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12th November 2014 @ 04:48

Crude from: http://malaria.ourexperiment.org/triazolopyrazine_se/11186/Synthesis_of_2chloro6hydrazinylpyrazine_SGS_11.html

Using modified procedure from:

http://malaria.ourexperiment.org/triazolopyrazine_se/11087/Synthesis_of_2chloro624difluoromethoxybenzylidenehydrazinylpyrazine_AEW_2041.html

Resynthesis of JU 2-4:

http://malaria.ourexperiment.org/triazolopyrazine_se/9977/Synthesis_of_426Chloropyrazin2ylhydrazonomethylbenzonitrile_JU_24.html

Reaction performed by Will Talbot and Hugh Russell.

 

 

 

1.36 g of crude SGS 1-1 was stirred into MeCN (12 mL) along with 4-formylbenzonitrile (1.00 g). Glacial AcOH (0.45 mL) was added and the mixture (a light brown suspension) was stirred overnight at room temperature.

Attached Files
7th November 2014 @ 07:02

Resynthesis of TM 34-4

Resynthesis of 2-chloro-6-hydrazinylpyrazine (TM 34-3).

Reaction performed by William Talbot, Sebastian Schwartz and Hugh Russell.

 

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

 

2,6-dichloropyrazine (21 g, 141 mmol) was dissolved in 100 mL EtOH and hydrazine hydrate (13.5 mL, 270 mmol) was added. The mixture was stirred under reflux for 7 h.  At this time tlc (DCM) showed the presence of a new material (Rf =0.21).  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. 

11.84 g of crude was produced.

 

SMILES

ClC1=CN=CC(Cl)=N1 to

ClC1=CN=CC(NN)=N1

InChI

InChI=1S/C4H2Cl2N2/c5-3-1-7-2-4(6)8-3/h1-2H to

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

Attached Files