Tag Archives: Malaria

the third step to synthesis 5-chloro-3-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyrazine

summary

this step is order to synthesis 5-chloro-3-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyrazine to analysis the possible to form the target product

3.png

 

reference

 I just write the procedure to refer to the reference ( in the blow) and I am confused about the extraction agent is suitable for my product. Therefore, I highlight about the latter part.

 

https://au mynotebook.labarchives.com/doc/view/NjMuN3wyNTQyNC80OS9FbnRyeVBhcnQvNzI4NTI1MjA2fDE2MS4 nb_id=MzMwNTEuMjAwMDAwMDAwMDA0fDI1NDI0LzI1NDI0L05vdGVib29rLzg5MjQwOTYxNHw4Mzg5OS4y&page_num=0

procedure

Compound

Amount

(mg or mL)

n (mmol)

eq.

MW

density

 (if liquid)

(E)-2-Chloro-(2-(4-chloro)-benzylidene)hydrazineyl)prazine

0.6g

2.26mmol

1

265.13g/mol

 

(Diacetoxyiodo)benzene_____(PIDA)

0.79g

2.46mmol

1.09

322.096g/mol

 

DCM(CH2Cl2)

20ml

 

 

84.93g/mol

 

saturated solution

25ml

 

 

84.007 g/mol

 

 

 

 

 

 

 

5-chloro-3-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyrazine

 

NONE

 

 

262.13g/mol

 


(E)-2-Chloro-(2-(4-chloro)-benzylidene)hydrazineyl)prazine (0.6 g, 2.26mmol, 1 equiv.) was dissolved in DCM (16.7 mL) and PhI(OAc)2 (0.79g, 2 mmol, 1 equiv.) was added. The solution was stirred at rt for 2 hours. The reaction was diluted with DCM (4.75 mL) and quenched using sat. NaHCO3  (12.5 mL). The aqueous layer was extracted with DCM (8.35 mL) and the combined organic layers were washed with a sat. NaHCO3 (12.5mL) and brine (8.35 mL). The organic layer was dried with MgSO4 and concentrated under reduced pressure.  Then we get the 0.173g yellow crystal. The therapoy is 29.2%


risk assesment

Risk Assesment from yang.pdf


data 

TLC

531849928049343842.jpg


the nmr analysis will be published next time



the second step to synthesis the (E)-2-Chloro-(2-(4-chloro)-benzylidene)hydrazineyl)prazine

 

summary

 This is  the second to (E)-2-chloro-(2-(4-chloro)-benzylidene)hydrazineyl)prazine and the experiment will do the next step to synthesis the next product

 

step2NEW.png

 

Reference

Synthesis of 2-chloro-6-hydrazinylpyrazine #2

 

Procedure

Compound

Amount

(mg or mL)

n (mmol)

eq.

MW

density

 (if liquid)

2-Chloro-6-hydrazinylpyrazine

1g

6.91

1

144.56g/mol

 

4-chlorobenzaldehyde

0.97g

6.91

0.97

140.57g/mol

 

EtOH

24ml

 

 

46.07g/mol

 

(E)-2-Chloro-(2-(4-chloro)-benzylidene)hydrazineyl)prazine

NONE

 

 

265.13g/mol

 

 

 

 

 

 

 

 

 

 

 

 

 

2-chloro-6-hydrazinylpyrazine (1g)was stirred into a solution of ethanol (24mL). 4-chlorobenzaldehyde (0.97g) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 1 hours. The solvent was removed under reduced pressure the product was recrystallized in ethyl acetate to yield 2-chloro-6-[(E)-2-[(4-chlorophenyl)methylidene]hydrazin-1-yl]pyrazine as a white solid. NMR and mass spectrometry were used to fully characterize the compound. Then the experiment get the yellow crystal.

risk assessment

Risk Assesment from yang.pdf


DATA

260464514607168701.jpg


the nmr analysis will be publish next time. 

Biological Data from Dundee – July 2017 Compounds

A set of 26 Series 4 Triazolopyrazine compounds were sent to have their efficacy evaluated against Plasmodium flaciparum in-vitro at Dundee (GitHub issue #517)

The data has been posted here

Strings:

MMV1557931

IC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC(F)=C(F)C=C4)N32       InChI=1S/C19H13F2IN4O/c20-15-6-1-12(9-16(15)21)7-8-27-18-11-23-10-17-24-25-19(26(17)18)13-2-4-14(22)5-3-13/h1-6,9-11H,7-8H2                                                                       SYOXDOQMLHMQGB-UHFFFAOYSA-N

MMV1557932

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(C4=CC(F)=C(F)C=C4)=O)N32 InChI=1S/C20H12F4N4O3/c21-14-6-3-12(7-15(14)22)16(29)10-30-18-9-25-8-17-26-27-19(28(17)18)11-1-4-13(5-2-11)31-20(23)24/h1-9,20H,10H2                               OPCIMEMUOABUMK-UHFFFAOYSA-N

MMV1557933

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(OC)(OC)C4=CC(F)=C(F)C=C4)N32 InChI=1S/C22H18F4N4O4/c1-31-22(32-2,14-5-8-16(23)17(24)9-14)12-33-19-11-27-10-18-28-29-20(30(18)19)13-3-6-15(7-4-13)34-21(25)26/h3-11,21H,12H2,1-2H3                       HFRRKTROCJVLKP-UHFFFAOYSA-N

MMV1557934

FS(F)(F)(F)(F)C(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32   InChI=1S/C19H15F5N4OS/c20-30(21,22,23,24)16-8-6-15(7-9-16)19-27-26-17-12-25-13-18(28(17)19)29-11-10-14-4-2-1-3-5-14/h1-9,12-13H,10-11H2                             PEMORNCGKKXBCP-UHFFFAOYSA-N

MMV1557935

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4(CC5C6)CC6CC@@HC4)N32   InChI=1S/C24H26F2N4O2/c25-23(26)32-19-3-1-18(2-4-19)22-29-28-20-13-27-14-21(30(20)22)31-6-5-24-10-15-7-16(11-24)9-17(8-15)12-24/h1-4,13-17,23H,5-12H2/t15-,16?,17?,24?BSXLJNOXQMXUOB-CRFYJIHUSA-N

MMV1557936

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OC(C)CC4=CC=CC=C4)N32   InChI=1S/C21H18F2N4O2/c1-14(11-15-5-3-2-4-6-15)28-19-13-24-12-18-25-26-20(27(18)19)16-7-9-17(10-8-16)29-21(22)23/h2-10,12-14,21H,11H2,1H3                                         HJOHTEUEFDSADX-UHFFFAOYSA-N

MMV1557937

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC45CC@@HC[C@@h]6C4)N32   InChI=1S/C23H24F2N4O2/c24-22(25)31-18-3-1-17(2-4-18)21-28-27-19-11-26-12-20(29(19)21)30-13-23-8-14-5-15(9-23)7-16(6-14)10-23/h1-4,11-12,14-16,22H,5-10,13H2/t14-,15+,16-,23?PIOOGPDPQVQAFQ-QUXYOMGYSA-N

MMV1557938

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC4C[C@H]5C=C[C@@h]4C5)N32   InChI=1S/C20H18F2N4O2/c21-20(22)28-16-5-3-13(4-6-16)19-25-24-17-9-23-10-18(26(17)19)27-11-15-8-12-1-2-14(15)7-12/h1-6,9-10,12,14-15,20H,7-8,11H2/t12-,14+,15?/m0/s1 OMOCZBKUEFTIAC-DJIKBVBFSA-N

MMV1557939

CC1(C)[C@@h]2C[C@H]1C(CCOC3=CN=CC4=NN=C(C5=CC=C(OC(F)F)C=C5)N43)=CC2 InChI=1S/C23H24F2N4O2/c1-23(2)16-6-3-14(18(23)11-16)9-10-30-20-13-26-12-19-27-28-21(29(19)20)15-4-7-17(8-5-15)31-22(24)25/h3-5,7-8,12-13,16,18,22H,6,9-11H2,1-2H3/t16-,18-/m0/s1                                                                                             PQILDBPUDLGKJU-WMZOPIPTSA-N

MMV1557940

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(C4=CC=CC=C4)=O)N32 InChI=1S/C20H14F2N4O3/c21-20(22)29-15-8-6-14(7-9-15)19-25-24-17-10-23-11-18(26(17)19)28-12-16(27)13-4-2-1-3-5-13/h1-11,20H,12H2                                                         MQSMCJANEPVRGE-UHFFFAOYSA-N

MMV1557941

ClC(C=C1)=CC(Cl)=C1C2=NN=C3C=NC=C(OCC45CC@@HC[C@@h]6C4)N32 InChI=1S/C22H22Cl2N4O/c23-16-1-2-17(18(24)6-16)21-27-26-19-10-25-11-20(28(19)21)29-12-22-7-13-3-14(8-22)5-15(4-13)9-22/h1-2,6,10-11,13-15H,3-5,7-9,12H2/t13-,14+,15-,22?XRHQAPBKYTXPOW-HBJUSLLUSA-N

MMV1557942

ClC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC45CC@@HC[C@@h]6C4)N32 InChI=1S/C22H23ClN4O/c23-18-3-1-17(2-4-18)21-26-25-19-11-24-12-20(27(19)21)28-13-22-8-14-5-15(9-22)7-16(6-14)10-22/h1-4,11-12,14-16H,5-10,13H2/t14-,15+,16-,22?         MFXXXMMQULKXIX-GGTBJBEQSA-N

MMV1557943

CC1(C)[C@@h]2C[C@H]1C(CCOC3=CN=CC4=NN=C(C5=C(Cl)C=C(Cl)C=C5)N43)=CC2 InChI=1S/C22H22Cl2N4O/c1-22(2)14-4-3-13(17(22)9-14)7-8-29-20-12-25-11-19-26-27-21(28(19)20)16-6-5-15(23)10-18(16)24/h3,5-6,10-12,14,17H,4,7-9H2,1-2H3/t14-,17-/m0/s1 OYFPJLPMJIFAIS-YOEHRIQHSA-N

MMV1557944

CC1(C)[C@@h]2C[C@H]1C(CCOC3=CN=CC4=NN=C(C5=CC=C(Cl)C=C5)N43)=CC2 InChI=1S/C22H23ClN4O/c1-22(2)16-6-3-14(18(22)11-16)9-10-28-20-13-24-12-19-25-26-21(27(19)20)15-4-7-17(23)8-5-15/h3-5,7-8,12-13,16,18H,6,9-11H2,1-2H3/t16-,18-/m0/s1 BDWPPKIAXRRNII-WMZOPIPTSA-N

MMV1557945

ClC(C=C1)=CC(Cl)=C1C2=NN=C3C=NC=C(OCC4C[C@H]5C=C[C@@h]4C5)N32 InChI=1S/C19H16Cl2N4O/c20-14-3-4-15(16(21)7-14)19-24-23-17-8-22-9-18(25(17)19)26-10-13-6-11-1-2-12(13)5-11/h1-4,7-9,11-13H,5-6,10H2/t11-,12+,13?/m0/s1                         OLAUIVKJLBCHFE-LAGVYOHYSA-N

MMV1557946

ClC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC4C[C@H]5C=C[C@@h]4C5)N32 InChI=1S/C19H17ClN4O/c20-16-5-3-13(4-6-16)19-23-22-17-9-21-10-18(24(17)19)25-11-15-8-12-1-2-14(15)7-12/h1-6,9-10,12,14-15H,7-8,11H2/t12-,14+,15?/m0/s1                       OWTVMOKESSEJOP-DJIKBVBFSA-N

MMV1557948

O=C(NC1=CC=NC=C1)C2=CN=CC3=NN=C(C4=CC=CC=C4)N32               InChI=1S/C17H12N6O/c24-17(20-13-6-8-18-9-7-13)14-10-19-11-15-21-22-16(23(14)15)12-4-2-1-3-5-12/h1-11H,(H,18,20,24)                                                                               JWMBXLLOVDKXRE-UHFFFAOYSA-N

MMV1557947

C12=NN=C(C3=CC=NC=C3)N1C(OCCC4=CC=CC=C4)=CN=C2                   InChI=1S/C18H15N5O/c1-2-4-14(5-3-1)8-11-24-17-13-20-12-16-21-22-18(23(16)17)15-6-9-19-10-7-15/h1-7,9-10,12-13H,8,11H2                                                                           BSTOZULDVQMNLS-UHFFFAOYSA-N

MMV1557950

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OC/C(C4=CC=CC=C4)=N/O)N32 InChI=1S/C20H15F2N5O3/c21-20(22)30-15-8-6-14(7-9-15)19-25-24-17-10-23-11-18(27(17)19)29-12-16(26-28)13-4-2-1-3-5-13/h1-11,20,28H,12H2/b26-16-                                   VJSBQKQNONLQQJ-QQXSKIMKSA-N

MMV1557949

FC(C=C1)=C(F)C=C1CCOC2=CN=CC3=NN=C(C4=CC=CC=C4)N32         InChI=1S/C19H14F2N4O/c20-15-7-6-13(10-16(15)21)8-9-26-18-12-22-11-17-23-24-19(25(17)18)14-4-2-1-3-5-14/h1-7,10-12H,8-9H2                                               RGEIFMMWUNGFHD-UHFFFAOYSA-N

MMV025100

NS(C1=CC(C2=CC3=NC=NC(N)=C3S2)=CC=C1)(=O)=O                     InChI=1S/C12H10N4O2S2/c13-12-11-9(15-6-16-12)5-10(19-11)7-2-1-3-8(4-7)20(14,17)18/h1-6H,(H2,13,15,16)(H2,14,17,18)                                                                               MQMXDJVOZKMSNT-UHFFFAOYSA-N

MMV897709

FC(C=C1)=C(F)C=C1C(OC)COC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3                           PERKBMZWWUEZNJ-UHFFFAOYSA-N

MMV1557952

FC(C=C1)=C(F)C=C1C@@HCOC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3/t18-/m0/s1         PERKBMZWWUEZNJ-SFHVURJKSA-N

MMV1557951

FC(C=C1)=C(F)C=C1C@HCOC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3/t18-/m1/s1         PERKBMZWWUEZNJ-GOSISDBHSA-N

MMV1557953

FC(C=C1)=C(F)C=C1C(OC)COC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3                           PERKBMZWWUEZNJ-UHFFFAOYSA-N

MMV1557962

C12=NN=C(N3CCCCC3)N1C(OCCC4=CC=CC=C4)=CN=C2                           InChI=1S/C18H21N5O/c1-3-7-15(8-4-1)9-12-24-17-14-19-13-16-20-21-18(23(16)17)22-10-5-2-6-11-22/h1,3-4,7-8,13-14H,2,5-6,9-12H2                                                               QFNWKXKUHMYRFI-UHFFFAOYSA-N

Biological Data from Dundee – July 2017 Compounds

A set of 26 Series 4 Triazolopyrazine compounds were sent to have their efficacy evaluated against Plasmodium flaciparum in-vitro at Dundee (GitHub issue #517)

The data has been posted here

Strings:

MMV1557931

IC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC(F)=C(F)C=C4)N32       InChI=1S/C19H13F2IN4O/c20-15-6-1-12(9-16(15)21)7-8-27-18-11-23-10-17-24-25-19(26(17)18)13-2-4-14(22)5-3-13/h1-6,9-11H,7-8H2                                                                       SYOXDOQMLHMQGB-UHFFFAOYSA-N

MMV1557932

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(C4=CC(F)=C(F)C=C4)=O)N32 InChI=1S/C20H12F4N4O3/c21-14-6-3-12(7-15(14)22)16(29)10-30-18-9-25-8-17-26-27-19(28(17)18)11-1-4-13(5-2-11)31-20(23)24/h1-9,20H,10H2                               OPCIMEMUOABUMK-UHFFFAOYSA-N

MMV1557933

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(OC)(OC)C4=CC(F)=C(F)C=C4)N32 InChI=1S/C22H18F4N4O4/c1-31-22(32-2,14-5-8-16(23)17(24)9-14)12-33-19-11-27-10-18-28-29-20(30(18)19)13-3-6-15(7-4-13)34-21(25)26/h3-11,21H,12H2,1-2H3                       HFRRKTROCJVLKP-UHFFFAOYSA-N

MMV1557934

FS(F)(F)(F)(F)C(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32   InChI=1S/C19H15F5N4OS/c20-30(21,22,23,24)16-8-6-15(7-9-16)19-27-26-17-12-25-13-18(28(17)19)29-11-10-14-4-2-1-3-5-14/h1-9,12-13H,10-11H2                             PEMORNCGKKXBCP-UHFFFAOYSA-N

MMV1557935

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4(CC5C6)CC6CC@@HC4)N32   InChI=1S/C24H26F2N4O2/c25-23(26)32-19-3-1-18(2-4-19)22-29-28-20-13-27-14-21(30(20)22)31-6-5-24-10-15-7-16(11-24)9-17(8-15)12-24/h1-4,13-17,23H,5-12H2/t15-,16?,17?,24?BSXLJNOXQMXUOB-CRFYJIHUSA-N

MMV1557936

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OC(C)CC4=CC=CC=C4)N32   InChI=1S/C21H18F2N4O2/c1-14(11-15-5-3-2-4-6-15)28-19-13-24-12-18-25-26-20(27(18)19)16-7-9-17(10-8-16)29-21(22)23/h2-10,12-14,21H,11H2,1H3                                         HJOHTEUEFDSADX-UHFFFAOYSA-N

MMV1557937

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC45CC@@HC[C@@h]6C4)N32   InChI=1S/C23H24F2N4O2/c24-22(25)31-18-3-1-17(2-4-18)21-28-27-19-11-26-12-20(29(19)21)30-13-23-8-14-5-15(9-23)7-16(6-14)10-23/h1-4,11-12,14-16,22H,5-10,13H2/t14-,15+,16-,23?PIOOGPDPQVQAFQ-QUXYOMGYSA-N

MMV1557938

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC4C[C@H]5C=C[C@@h]4C5)N32   InChI=1S/C20H18F2N4O2/c21-20(22)28-16-5-3-13(4-6-16)19-25-24-17-9-23-10-18(26(17)19)27-11-15-8-12-1-2-14(15)7-12/h1-6,9-10,12,14-15,20H,7-8,11H2/t12-,14+,15?/m0/s1 OMOCZBKUEFTIAC-DJIKBVBFSA-N

MMV1557939

CC1(C)[C@@h]2C[C@H]1C(CCOC3=CN=CC4=NN=C(C5=CC=C(OC(F)F)C=C5)N43)=CC2 InChI=1S/C23H24F2N4O2/c1-23(2)16-6-3-14(18(23)11-16)9-10-30-20-13-26-12-19-27-28-21(29(19)20)15-4-7-17(8-5-15)31-22(24)25/h3-5,7-8,12-13,16,18,22H,6,9-11H2,1-2H3/t16-,18-/m0/s1                                                                                             PQILDBPUDLGKJU-WMZOPIPTSA-N

MMV1557940

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(C4=CC=CC=C4)=O)N32 InChI=1S/C20H14F2N4O3/c21-20(22)29-15-8-6-14(7-9-15)19-25-24-17-10-23-11-18(26(17)19)28-12-16(27)13-4-2-1-3-5-13/h1-11,20H,12H2                                                         MQSMCJANEPVRGE-UHFFFAOYSA-N

MMV1557941

ClC(C=C1)=CC(Cl)=C1C2=NN=C3C=NC=C(OCC45CC@@HC[C@@h]6C4)N32 InChI=1S/C22H22Cl2N4O/c23-16-1-2-17(18(24)6-16)21-27-26-19-10-25-11-20(28(19)21)29-12-22-7-13-3-14(8-22)5-15(4-13)9-22/h1-2,6,10-11,13-15H,3-5,7-9,12H2/t13-,14+,15-,22?XRHQAPBKYTXPOW-HBJUSLLUSA-N

MMV1557942

ClC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC45CC@@HC[C@@h]6C4)N32 InChI=1S/C22H23ClN4O/c23-18-3-1-17(2-4-18)21-26-25-19-11-24-12-20(27(19)21)28-13-22-8-14-5-15(9-22)7-16(6-14)10-22/h1-4,11-12,14-16H,5-10,13H2/t14-,15+,16-,22?         MFXXXMMQULKXIX-GGTBJBEQSA-N

MMV1557943

CC1(C)[C@@h]2C[C@H]1C(CCOC3=CN=CC4=NN=C(C5=C(Cl)C=C(Cl)C=C5)N43)=CC2 InChI=1S/C22H22Cl2N4O/c1-22(2)14-4-3-13(17(22)9-14)7-8-29-20-12-25-11-19-26-27-21(28(19)20)16-6-5-15(23)10-18(16)24/h3,5-6,10-12,14,17H,4,7-9H2,1-2H3/t14-,17-/m0/s1 OYFPJLPMJIFAIS-YOEHRIQHSA-N

MMV1557944

CC1(C)[C@@h]2C[C@H]1C(CCOC3=CN=CC4=NN=C(C5=CC=C(Cl)C=C5)N43)=CC2 InChI=1S/C22H23ClN4O/c1-22(2)16-6-3-14(18(22)11-16)9-10-28-20-13-24-12-19-25-26-21(27(19)20)15-4-7-17(23)8-5-15/h3-5,7-8,12-13,16,18H,6,9-11H2,1-2H3/t16-,18-/m0/s1 BDWPPKIAXRRNII-WMZOPIPTSA-N

MMV1557945

ClC(C=C1)=CC(Cl)=C1C2=NN=C3C=NC=C(OCC4C[C@H]5C=C[C@@h]4C5)N32 InChI=1S/C19H16Cl2N4O/c20-14-3-4-15(16(21)7-14)19-24-23-17-8-22-9-18(25(17)19)26-10-13-6-11-1-2-12(13)5-11/h1-4,7-9,11-13H,5-6,10H2/t11-,12+,13?/m0/s1                         OLAUIVKJLBCHFE-LAGVYOHYSA-N

MMV1557946

ClC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC4C[C@H]5C=C[C@@h]4C5)N32 InChI=1S/C19H17ClN4O/c20-16-5-3-13(4-6-16)19-23-22-17-9-21-10-18(24(17)19)25-11-15-8-12-1-2-14(15)7-12/h1-6,9-10,12,14-15H,7-8,11H2/t12-,14+,15?/m0/s1                       OWTVMOKESSEJOP-DJIKBVBFSA-N

MMV1557948

O=C(NC1=CC=NC=C1)C2=CN=CC3=NN=C(C4=CC=CC=C4)N32               InChI=1S/C17H12N6O/c24-17(20-13-6-8-18-9-7-13)14-10-19-11-15-21-22-16(23(14)15)12-4-2-1-3-5-12/h1-11H,(H,18,20,24)                                                                               JWMBXLLOVDKXRE-UHFFFAOYSA-N

MMV1557947

C12=NN=C(C3=CC=NC=C3)N1C(OCCC4=CC=CC=C4)=CN=C2                   InChI=1S/C18H15N5O/c1-2-4-14(5-3-1)8-11-24-17-13-20-12-16-21-22-18(23(16)17)15-6-9-19-10-7-15/h1-7,9-10,12-13H,8,11H2                                                                           BSTOZULDVQMNLS-UHFFFAOYSA-N

MMV1557950

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OC/C(C4=CC=CC=C4)=N/O)N32 InChI=1S/C20H15F2N5O3/c21-20(22)30-15-8-6-14(7-9-15)19-25-24-17-10-23-11-18(27(17)19)29-12-16(26-28)13-4-2-1-3-5-13/h1-11,20,28H,12H2/b26-16-                                   VJSBQKQNONLQQJ-QQXSKIMKSA-N

MMV1557949

FC(C=C1)=C(F)C=C1CCOC2=CN=CC3=NN=C(C4=CC=CC=C4)N32         InChI=1S/C19H14F2N4O/c20-15-7-6-13(10-16(15)21)8-9-26-18-12-22-11-17-23-24-19(25(17)18)14-4-2-1-3-5-14/h1-7,10-12H,8-9H2                                               RGEIFMMWUNGFHD-UHFFFAOYSA-N

MMV025100

NS(C1=CC(C2=CC3=NC=NC(N)=C3S2)=CC=C1)(=O)=O                     InChI=1S/C12H10N4O2S2/c13-12-11-9(15-6-16-12)5-10(19-11)7-2-1-3-8(4-7)20(14,17)18/h1-6H,(H2,13,15,16)(H2,14,17,18)                                                                               MQMXDJVOZKMSNT-UHFFFAOYSA-N

MMV897709

FC(C=C1)=C(F)C=C1C(OC)COC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3                           PERKBMZWWUEZNJ-UHFFFAOYSA-N

MMV1557952

FC(C=C1)=C(F)C=C1C@@HCOC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3/t18-/m0/s1         PERKBMZWWUEZNJ-SFHVURJKSA-N

MMV1557951

FC(C=C1)=C(F)C=C1C@HCOC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3/t18-/m1/s1         PERKBMZWWUEZNJ-GOSISDBHSA-N

MMV1557953

FC(C=C1)=C(F)C=C1C(OC)COC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3                           PERKBMZWWUEZNJ-UHFFFAOYSA-N

MMV1557962

C12=NN=C(N3CCCCC3)N1C(OCCC4=CC=CC=C4)=CN=C2                           InChI=1S/C18H21N5O/c1-3-7-15(8-4-1)9-12-24-17-14-19-13-16-20-21-18(23(16)17)22-10-5-2-6-11-22/h1,3-4,7-8,13-14H,2,5-6,9-12H2                                                               QFNWKXKUHMYRFI-UHFFFAOYSA-N

Synthesis of 5-chloro-[1,2,4]triazolo[4,3-a]pyrazine #2

Summary

This is the 2nd step and is the process of synthesising 5-chloro-[1,2,4]triazolo[4,3-a]pyrazine. There will be another two reactions after this, to create the brominated "Jasper 3" compund to test its functionalities.


Reference

Synthesis of 5-chloro-[1,2,4]triazolo[4,3-a]pyrazine

 

Reaction

JT_2-1_.PNG

 

Procedure 

7.44g of 2-chloro-6-hydrazinylpyrazine was dissolved using 75ml of toluene, 9ml of Triethyl orthoformate and 0.9g of TsOH. It was then heated and stirred for (Insert when reflux is done and continue procedure) 

 

Risk Assessment 

WIll be uploaded when my laptop gets fixed 

 

Data 

TLC and NMR will be uploaded when the reaction is complete 

 

Compound strings 

Synthesis of 2-chloro-6-hydrazinylpyrazine #2

Summary

This is the first step, synthesising 2-Chloro-6-hydrazinylpyrazine. There will be another 3 reactions after this, to create the brominated "Jasper 3" compund to test its functionalities. This is a repeat of the first experiment, except purification will be done before moving onto the next experiment and more starting product will be used. Differing amounts of solvents were used as well to test for better yielding methods. 


References 

Synthesis of 2-Chloro-6-hydrazinylpyrazine

 

Procedure

7.45g of 2,6-dichloropyrazine will be placed in an RB flask. 52ml of Isopropanol was then be added to the flask with 6.2ml of hydrazine  added with a syringe. The flask was then be attached to the reflux apparatus and refluxed at 100C for 3 hours. TLC was done after 3 hours and 10mins and showed a complete reaction. The sample will then be cooled down to room temperature, placed in an ice bath, where it started to solidify. It was then filtered twice with isopropanol and once with diethyl ether and placed under vacuum to remove the solvents. 

 

Risk assessment 

Lachlan Klein Risk Assesment form ex 1.doc

 

Data

TLC will be uploaded when the NMR is complete 

 

Compound strings

 

 

Synthesis of 5-chloro-[1,2,4]triazolo[4,3-a]pyrazine #1

Summary

This is the 2nd step and is the process of synthesising 5-chloro-[1,2,4]triazolo[4,3-a]pyrazine. There will be another two reactions after this, to create the brominated "Jasper 3" compund to test its functionalities.

The experiment yieleded only 40mg of possible product and was found to be not pure and therefore the experiment has been restarted from the beginning 


Reference

Synthesis of 5-chloro-[1,2,4]triazolo[4,3-a]pyrazine

 

Reaction

 

JT_2-1_.PNG

 

Procedure 

1.01g of 2-chloro-6-hydrazinylpyrazine was dissolved using 10ml of toluene, 1.20ml of Triethyl orthoformate and 120mg of TsOH. It was then heated and stirred for 24 hours and the solvents removed under reduced pressure. There was a yield of 40mg which was insufficient in progressing with the experiment. 

 

Risk Assessment 

 WIll be uploaded soon 

 

Data 

There were no TLC's recorded for this experiment

 

Compound strings

Synthesis of 2-Chloro-6-hydrazinylpyrazine

Summary:

The 2-Chloro-6-hydrazinylpyrazine is the first step of the whole experiment. The method of experiment is created by Jasper Tyler.


Reference:

Synthesis of 2-Chloro-6-hydrazinylpyrazine

 

Reation:


Procedure:

Equipment required: Flasks; Stirrer hot plate; Oil bath; Condenser; High vacuum pump; Separating funnel.

 

  1. Dissolve 2,6-dichloropyrazin(2.1g, 14.1mmol, 1eq) in EtOH(28mL) and add hydrazine hydrate(1.35mL, 8.1mmol, 2eq);
  2. Stir the reaction mixture at reflux for 3 hours and remove the solvent;
  3. Add water(20ml) and EtOAc(25mL) to dissolve all the solid;
  4. Extract the aqueous layer with EtOAc(3*10mL) and wash the combined organic layers with brine(5mL);
  5. Dry the mixture with MgSO4.

Risk Assessment


Data

The data will be uploaded once the experiment is complete.



Synthesis of 2-chloro-6-hydrazinylpyrazine #2

Summary

This is the first step, synthesising 2-Chloro-6-hydrazinylpyrazine. There will be another 3 reactions after this, to create the brominated "Jasper 3" compund to test its functionalities. This is a repeat of the first experiment, except purification will be done before moving onto the next experiment. 


References 

Synthesis of 2-Chloro-6-hydrazinylpyrazine

 

Reaction

step1.png

 

Procedure

Approxiametly 2g of 2,6-dichloropyrazine will be placed in an RB flask. 10ml of EtOH will then be added to the flask with 1.4ml of hydrazine  added with a syringe. The flask will then be attached to the reflux apparatus and refluxed at 100C for 3 hours. TLC will be done at 3 hours to monitor the reaction. The sample will then be cooled down to room temperature, the solvent evaporated and the sample dried using high vacuum. Purification will be done using column chromatography and the NMR will then be analysed.

 

Risk assessment 

Lachlan Klein Risk Assesment form ex 1.doc

 

Data

The data will be uploaded once the experiment is complete.


Compound strings

Synthesis of 3-bromo-5-chloro-[1,2,4]triazolo[4,3-a]pyrazine

Reaction Scheme:

Step3ReactionScheme.png

Compound

MW (g/mol)

Mol (mmol)

Mass (g)

Density (g/mL)

Volume (mL)

Equiv

5-chloro-[1,2,4]triazolo[4,3-a]pyrazine

154

1.69

0.26

 

 

1

NBS

177.98

1.52

0.281

 

 

0.9

Chloroform

 

 

 

 

15

 

3-bromo-5-chloro-[1,2,4]triazolo[4,3-a]pyrazine

231.92

1.69

0.392

 

 

1

 

Procedure:

6/14/17 NBS was recrystallized before the reaction. Water (35 ml) was added to NBS (3 g). The mixture was stirred and heated at 100 celsius degree until NBS was dissolved to make a yellow solution. The solution was cooled to room temperature. White crystals formed. The crystals were filtered out and washed with ice water. The crystals were placed on the high vac in a dessicator over P2O5 to dry overnight.

7/5/17 5-chloro-[1,2,4]triazolo[4,3-a]pyrazine (0.26 g, 2 mmol) and N-bromosuccinimide (0.281 g, 1.6 mmol, 0.9equiv.) were placed in chloroform (50 mL) and refluxed for 44 h. Reflux started at 10:30 am.

7/6/17 TLC showed that there was still starting material. Another 0.5 equivalents of NBS were added to the reaction. TLC at 2:00 pm still showed a lot of starting material.

7/7/17 TLC still showed mostly starting material. There seems to be a faint product spot. Another 0.5 equivalents of NBS were added, but TLC at the end of the day was still the same, so reaction was stopped. Flask was kept covered with aluminum foil to block light.

BrClfinalTLC.png

7/19/17 Solvent removed under reduced pressure. NMR showed that some product had formed, but there was still unreacted starting material.

NMRcrudeBrCl.png

7/21/17 Product was purified by column chromatography using 70:30 EtOAc: Hexanes. The NBS came off first, followed by the product. Solvent was removed under reduced pressure to yield a yellow solid (0.37 g, 1.6 mmol, 94% yield). NMR obtained.

BrClFinalNMR.png