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28th July 2015 @ 01:27

Reaction Scheme 

 

Summary

 This experiment will not be carried out.

Hazard & Risk Assessment

 

HIRAC CX 1-1.doc

 

References

 

http://malaria.ourexperiment.org/triazolopyrazine_se/10045/Synthesis_of_5chloro34difluoromethoxyphenyl124triazolo43apyrazine_AEW_205.html

 

http://malaria.ourexperiment.org/triazolopyrazine_se/10705/5chloro34difluoromethoxyphenyl124triazolo43apyrazine_JU_191.html

 

InChi Strings

InChI=1S/C11H8Cl2N4/c12-9-3-1-8(2-4-9)5-15-17-11-7-14-6-10(13)16-11/h1-7H,(H,16,17)/b15-5+

to

InChI=1S/C11H6Cl2N4/c12-8-3-1-7(2-4-8)11-16-15-10-6-14-5-9(13)17(10)11/h1-6H

 

SMILES

ClC1=CN=CC(N/N=C/C2=CC=C(Cl)C=C2)=N1

to

ClC1=CN=CC2=NN=C(C3=CC=C(Cl)C=C3)N21

 

Attached Files
27th July 2015 @ 01:49

Desired product was obtained. Recrystalization failed. Reaction was discarded.

Reaction started at 14:49. Reached temp at 15:05.

Procedure

5-Chloro-[1,2,4]triazolo[4,3-a]pyrazine (1 g, 6.49 mmol) and NBS (2 g, 11.2 mmol, 1.7 equiv.) were placed in chloroform (50 mL) and refluxed for 24 h. The reaction mixture was diluted with chloroform (50 mL), washed with saturated carbonate solution (20mL). The aqueous layer was then re-extracted with chloroform (3*40mL). The combined organic was then washed with brine (40ml) and the solvent was removed under reduced pressure to give a brown solid.

NMR of the crude showed that purification was needed. The solid was then purified by recrystallization in methanol (10ml) but did not dissolve well in methanol. Pale yellow solid was obtained. Ended up with mess.

Reaction was discarded.

Data

NMR data of the crude:

TZ 4-1 crude.pdf
 

HIRAC

 

HIRAC TZ 4-1.pdf

Strings

ClC1=CN=CC2=NN=CN21
to 
ClC1=CN=CC2=NN=C(Br)N21

InChI=1S/C5H3ClN4/c6-4-1-7-2-5-9-8-3-10(4)5/h1-3H
to
InChI=1S/C5H2BrClN4/c6-5-10-9-4-2-8-1-3(7)11(4)5/h1-2H


Attached Files
23rd July 2015 @ 06:16

SSP-3 original composition was a brown liquid. Solvent was evaporated and TLC was performed under various conditions to determine the eluent with the best seperating ability. An 8:2 ethyl acetate: petroleum eluent was used to run SSP-3 in a silica column (25g). A TLC in 8:2 ethyl acetate: petroleum was perfomed to determine fractions which contained the desired product, which were combined into a flask. The solvent was then evaporated under vacuum. The final product yield was 126mg and had a beige, solid appearance.

SSP-3

 

Strings:


SMILES:

ClC1=CC=CC(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)=C1

InChl:

InChI=1S/C19H15ClN4O/c20-16-8-4-7-15(11-16)19-23-22-17-12-21-13-18(24(17)19)25-10-9-14-5-2-1-3-6-14/h1-8,11-13H,9-10H2

Attached Files
23rd July 2015 @ 05:55

SSP-1 was washed with ethyl acetate (~100mL) and then dried.TLC under different conditions was perfomed to determine eluent with best seperation. SSP-1 was then run in a silica column (25g)  with a 9:1 DCM:Acetone eluent. The purified fraction were combined in a flask and the solvent was evaporated off. 1H NMR (200mHz, CDCl3) determined that the final product still contained impurities. A second silica column (25g) was run in a 8:2 ethyl acetate: petroleum eluent. Solvent was evaporated to yield 210.4 mg of product, which had a yellow solid appearance. 1H NMR (200mHz, CDCl3) determined that the final product still contained impurities.

                                SSP-1

 

 

Strings: 

SMILES

C12=NN=C(C3=CC=CC=C3)N1C(OCCC4=CC=CC=C4)=CN=C2

InCHl

InChI=1S/C19H16N4O/c1-3-7-15(8-4-1)11-12-24-18-14-20-13-17-21-22-19(23(17)18)16-9-5-2-6-10-16/h1-10,13-14H,11-12H2

Attached Files
20th July 2015 @ 13:13


Procedure: Started 14:00 20th July 2015

Crude AEW 246-1 was dissolved in 4M HCl in Dioxane (10 mL) and stirred at room temperature.

InChi:

CC(OC(N(CCC1)CC1C2=NN=C3N2C(OCC(OC4OCCCC4)C5=CC=CC=C5)=CN=C3)=O)(C)C

to

OC(C1=CC=CC=C1)COC2=CN=CC3=NN=C(C4CNCCC4)N32

InChI=1S/C28H37N5O5/c1-28(2,3)38-27(34)32-14-9-12-21(18-32)26-31-30-23-16-29-17-24(33(23)26)36-19-22(20-10-5-4-6-11-20)37-25-13-7-8-15-35-25/h4-6,10-11,16-17,21-22,25H,7-9,12-15,18-19H2,1-3H3

to

InChI=1S/C18H21N5O2/c24-15(13-5-2-1-3-6-13)12-25-17-11-20-10-16-21-22-18(23(16)17)14-7-4-8-19-9-14/h1-3,5-6,10-11,14-15,19,24H,4,7-9,12H2

Attached Files