Diisopropylethylamine → 7-amino-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid 8 (32 mg, 0.164 mmol), HATU (74.8 mg, 0.197 mmol) and DIPEA (0.054 mL, 0.328 mmol) in DMF (2 mL) was stirred for 15 at rt. N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide 67 (48.2 mg, 0.164 mmol) was added and stirred overnight at 80° C. The reaction mixture was poured in cold citric acid solution and the resulting precipitate was collected. Purification by HPLC gave the title compound 7-amino-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 70 (14 mg, 18%). NMR (400 MHz, DMSO-d6) 2.23 (s, 3H), 7.07 (s, 2H), 7.28 (d, J=8.2 Hz, 1H), 7.62 (dd, J=8.2 Hz and 2.0 Hz, 1H), 7.79 (t, J=7.8 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.97 (d, J=7.8 Hz, 1H), 8.28 (d, J=8.2 Hz, 1H), 8.31 (s, 1H), 8.78 (dd, J=5.1 Hz and 2.3 Hz, 2H), 9.48 (s, 1H), 10.49 (s, 1H). (m/z)=472 (M+H)+.

Provenance & Evidence