Methyl 3-(3-thienyl)benzoate → N-(2-methyl-5-(3-(thiophen-3-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride 29 (73.5 mg, 0.229 mmol) in toluene (1.5 mL) was added trimethylaluminum (0.458 mL, 0.916 mmol) and was stirred for 15 min. methyl 3-(thiophen-3-yl)benzoate 82 (50 mg, 0.229 mmol) in toluene (1.5 mL) was added. The reaction mixture was stirred overnight at 60° C. Quenched with a saturated solution of NaHCO3 and extracted twice with EtOAc. Organic layer was washed with brine, dried, and evaporated. Purification by HPLC gave the title compound N-(2-methyl-5-(3-(thiophen-3-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 83 (6 mg, 5%). NMR (400 MHz, DMSO-d6) 2.27 (s, 3H), 7.32 (d, J=8.2 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.64-7.72 (m, 3H), 7.87 (d, J=7.8 Hz, 1H), 7.91 (d, J=2.3 Hz, 1H), 7.94 (d, J=7.8 Hz, 1H), 8.01 (dd, 2.7 Hz and 1.6 Hz, 1H), 8.27 (t, J=1.6 Hz, 1H), 8.55 (s, 1H), 8.76 (d, J=2.3 Hz, 1H), 8.89 (d, J=2.3 Hz, 1H), 10.37 (s, 1H), 10.53 (s, 1H). (m/z)=471 (M+H)+.

Provenance & Evidence