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3rd June 2014 @ 05:38

Reaction completed successfully, giving ~60 % yield of pure TM 24-1 after flash chromatography.

scheme

TM 22-1 (from Synthesis of N-(5-chloro-2-methylphenyl)-6-hydrazinylpyrazine-2-carboxamide (TM 22-1): 300 mg, crude, 1.08 mmol if pure) was combined with 4-difluoromethoxybenzaldehdye (186 mg, 1.08 mmol, 1 eq) and catalytic AcOH (~0.1 mL) in MeCN (5 mL), and stirred at RT for 4 h.

Volatiles were removed under vacuum, and the crude product was purified by automatic column chromatography (eluent: 5 -> 40 % EtOAc : hexanes), giving 271 mg (0.63 mmol, 58 % assuming (unjustifiably) that TM 22-1 was pure) of pure TM 24-1 as bright yellow flakes.

 

Pure NMR:

1H (DMSO-d6, 400 MHz):

TM 24-1 1H DMSO 400 MHz.pdf

13C (DMSO-d6, 200 MHz):

TM 24-1 13C DMSO 400 MHz.pdf

TM 24-1 CHARACTERISATION.zip

 

1H (DMSO-d6, 200 MHz):

TM 24-1 pure 1H DMSO 200 MHz.pdf

TM 24-1 pure DMSO.zip

 

InChI:

InChI=1S/C12H12ClN5O/c1-7-2-3-8(13)4-9(7)17-12(19)10-5-15-6-11(16-10)18-14/h2-6H,14H2,1H3,(H,16,18)(H,17,19)

InChI=1S/C8H6F2O2/c9-8(10)12-7-3-1-6(5-11)2-4-7/h1-5,8H

to

InChI=1S/C20H16ClF2N5O2/c1-12-2-5-14(21)8-16(12)27-19(29)17-10-24-11-18(26-17)28-25-9-13-3-6-15(7-4-13)30-20(22)23/h2-11,20H,1H3,(H,26,28)(H,27,29)/b25-9+

HIRAC:

24-1 hirac.pdf
Linked Posts
Attached Files
24-1 hirac.pdf
scheme.png
TM 24-1 pure 1H DMSO 200 MHz.pdf
TM 24-1 pure DMSO.zip
TM 24-1 1H DMSO 400 MHz.pdf
TM 24-1 13C DMSO 400 MHz.pdf
TM 24-1 CHARACTERISATION.zip