Triazolopyrazine Series

Synthesis of (E )-2-chloro-6-(2-(pyridin-3-methylene)hydrazinyl)pyrazine   (SGS 3-1)

12th November 2014 @ 17:10

Synthesis of SGS 3-1 (AEW 199-1)

http://malaria.ourexperiment.org/triazolopyrazine_se/byuser/www.google.com-accounts-o8-id-id=AItOawmEjK3bt7yI4QzJmveCLN2gxtJpm9NpHqk/page/3

Reaction performed by Jason Chami, Evan Hockings, James Kalas, James Manton-Hall, Andreas Orsmond, Mackenzie Shaw and Alex Su.

SGS 1-1 (1.01 g, 6.99 mmol) was added to 0.756 g (7.06 mmol) of 3-pyridinecarboxaldehyde with 0.45 mL of glacial acetic acid and 12 mL of MeCN solvent.  This was stirred at room temperature for 48 h. Volatiles were removed in vacuo to produce a pale brown solid which still smelt of AcOH.

To remove the AcOH, the pale brown solid as dissolved in DCM (200 mL), washed twice with aqueous NaHCO_3, then dried over MgSO₄, and filtered. The solvent was removed in vacuo to produce a pale brown solid.

The TLC shows the starting material (SGS 1-1) and SGS 3-1 prior to extraction (SGS 3-1 Crude) and after washing with NaHCO₃ (SGS 3-1 Extraction).  The extracted SGS 3-1 looks no purer that than the starting material from the results of the TLC but it no longer smelt of AcOH.

SMILES                

ClC1=CN=CC(NN)=N1 and 

O=C([H])C1=CN=CC=C1 to 

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

InChI

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

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

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