Trimethylaluminum → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-(2,2,2-trifluoroacetamido)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 5 (25 mg, 0.085 mmol) and trimethylaluminum (0.170 mL, 0.341 mmol) in toluene (1 mL) was stirred for 30 min. Ethyl 7-(2,2,2-trifluoroacetamido)thieno[2,3-b]pyrazine-6-carboxylate 10 (27.2 mg, 0.085 mmol) in toluene (1 mL) was added and stirred overnight at 60° C. Poured in NaHCO3 solution and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated. Purification by chromatography (20->80 ethylacetate in CH2Cl2) gave the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-(2,2,2-trifluoroacetamido)thieno[2,3-b]pyrazine-6-carboxamide 44 (10 mg, 20%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.26 (s, 3H), 7.29 (d, J=8.2 Hz, 1H), 7.58-7.66 (m, 2H), 7.76 (d, J=8.2 Hz, 1H), 7.91-7.98 (m, 2H), 8.05 (s, 1H), 8.85 (s, 1H), 8.94 (s, 1H), 10.20 (br s, 1H), 10.38 (s, 1H), 11.80 (br s, 1H). (m/z)=567 (M+H)+.

Provenance & Evidence