Triethylamine → N-(5-(3-(3-(2-cyanopropan-2-yl)phenyl)ureido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2-cyanopropan-2-yl)benzoic acid 3 (50 mg, 0.264 mmol), diphenylphosphoryl azide (0.074 mL, 95 mg, 0.344 mmol) and triethylamine (0.110 mL, 0.793 mmol) in toluene (1 mL) was stirred at 100° C. for 1 h. N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride 29 (85 mg, 0.264 mmol) in THF (1 mL) was added and stirred at 90° C. for 1 h. Evaporated to dryness and purified by chromatography (0-50% EtOAc in CH2Cl2) to yield the title compound N-(5-(3-(3-(2-cyanopropan-2-yl)phenyl)ureido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 40 (88 mg, 70.8%). NMR (400 MHz, DMSO) 2.21 (s, 3H), 7.11 (m, 1H), 7.23 (m, 2H), 7.33 (t, J=7.8 Hz, 1H), 7.40 (m, 1H), 7.63 (d, J=1.9 Hz, 1H), 7.69 (t, J=1.9 Hz, 1H), 8.53 (s, 1H), 8.73 (s, 1H), 8.76 (d, J=2.3 Hz, 1H), 8.83 (s, 1H), 8.88 (d, J=2.3 Hz, 1H), 10.47 (s, 1H). (m/z)=471 (M+H)+.

Provenance & Evidence