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30th April 2015 @ 22:41

Reaction performed by Jason Chami, Evan Hockings, Alex Su and James Kalas 

First step in the synthesis (below) to prepare four chloroarylpyrazine cores.

 

2,6-dichloropyrazine (40.2 g, 270 mmol) was dissolved in 120 mL EtOH and hydrazine hydrate (27.2 mL, 540 mmol) was added. The mixture was stirred under reflux for 7 h.   The cooled, crude mixture was allowed to stand overnight.

The solvent was then removed from the crude mixture in vacuo, giving an orange mixture of oil and solid to which EtOAc (200mL) and  water (150mL) was added. The aqueous layer was removed and washed with EtOAc (3x 100mL). The combined organic layers were concentrated in vacuo to produce an orange crystalline solid. 

64.3 g of orange crude was produced. Tlc (DCM) showed the presence of a new material (Rf =0.6). 

 

TLC

12th November 2014 @ 05:55

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.

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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 NaHCO3, then dried over MgSO4, and filtered. The solvent was removed in vacuo to produce a pale brown solid.

 

Displaying IMG_1992.JPG

The TLC shows the starting material (SGS 1-1) and SGS 3-1 prior to extraction (SGS 3-1 Crude) and after washing with NaHCO(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+