Diisopropylethylamine → 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-2-(1-aminoethyl)-1-cyclopropyl-N-methyl-1H-benzo[d]imidazole-7-carboxamide (95 mg, 0.37 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (56.8 mg, 0.368 mmol) and 1,1′-dimethyltriethylamine (128 μL, 0.74 mmol) in n-butanol (2 mL) was stirred at 120° C. for 5 h. After cooling to rt, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using 0 to 10% gradient of MeOH in DCM-EtOAc (1:1) as eluent to give 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide: 1H NMR (400 MHz, DMSO-d6) δ 8.45-8.40 (m, 1H), 8.05 (s, 1H), 7.66 (d, J=8 Hz, 1H), 7.62 (d, J=4 Hz, 1H), 7.31 (br, 2H), 7.24 (d, J=8 Hz, 1H), 7.19 (dd, J=8, 8 Hz, 1H), 5.89-5.81 (m, 1H), 2.83 (d, J=4 Hz, 3H), 1.62 (d, J=8 Hz, 3H), 1.12-1.04 (m, 2H), 0.95-0.79 (m, 2H); LC-MS (ESI) m/z 377.2 [M+H]+.

Provenance & Evidence