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15th June 2015 @ 23:13

Reaction performed by Evan Hockings, Alex Su, James Kalas and James Manton-Hall.

SGS 4-3 (crude, 1.73 g, 7.4 mmol) was stirred into DCM (100 mL) along with PIDA (2.38 g, 7.4 mmol). The mixture (a dark green suspension) was stirred for 24 hours at room temperature.

The 6-2 was washed with saturated sodium hydrogencarbonate and then the organic layer was collected and solvent was removed by evaporation.

TLC:

InChI=1S/C10H6ClN5/c11-8-5-12-6-9-14-15-10(16(8)9)7-3-1-2-4-13-7/h1-6H

SMILES ClC1=CN=CC2=NN=C(C3=NC=CC=C3)N21

12th March 2015 @ 20:43

Resynthesis of SGS 4-1. 

SGS 1-2 (crude, 1.007 g, 7.1 mmol) was stirred into MeCN (12 ml). 3-Pyridinecarboxaldehyde (0.74 g, 6.9 mmol, density 1.137 g/mL) was added and the reaction mixture (light brown suspension) was observed. The reaction mixture was stirred at room temperature for 7 days. 

TLC

TLC

19th November 2014 @ 06:17

19 November 2014 @ 16:51

Synthesis of SGS 4-1 (AEW 198-1)

http://malaria.ourexperiment.org/triazolopyrazine_se/11058/Synthesis_of_E2chloro62pyridin2ylmethylenehydrazinylpyrazine_AEW_1982.html

Reaction performed by Jason Chami and Mackenzie Shaw.

SGS 1-1 (1.06 g, 7.33 mmol) was stirred into MeCN (15 mL). 2-Pyridinecarboxaldehyde (0.77 g, 7.2 mmol) and AcOH (0.4 mL) were added to the mixture.  This reaction mixture was then stirred at room temperature overnight.

TLC: 

TLC SGS 4-1

Synthesis of SGS 4-1

SMILES

ClC1=CN=CC(NN)=N1

and

O=C([H])C1=CC=CC=N1

to

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

 

InchI Strings

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)

and

InChI=1S/C6H5NO/c8-5-6-3-1-2-4-7-6/h1-5H

to


InChI=S/C10H8ClN5/c11-9-6-12-7-10(15-9)16-14-5-8-3-1-2-4-13-8/h1-7H,(H,15,16)/b14-5+