Diisopropylethylamine → 2-((1S)-1-((6-amino-5-(trifluoromethyl)-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 (Prepared in Example 20, 150 mg, 0.581 mmol), 6-chloro-5-(trifluoromethyl)pyrimidin-4-amine (172 mg, 0.871 mmol) and 1,1′-dimethyltriethylamine (202 μL, 1.161 mmol) in n-butanol (2 mL) was stirred at 120° C. After 42 h, the mixture was cooled to rt and 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) with 0.2% NH4OH as eluent to give 2-((1S)-1-((6-amino-5-(trifluoromethyl)-4-pyrimidinyl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide: 1H NMR (400 MHz, DMSO-d6) δ 8.50-8.41 (m, 1H), 8.05 (s, 1H), 7.66 (d, J=8 Hz, 1H), 7.28-7.18 (m, 2H), 6.90-6.78 (m, 2H), 5.89-5.81 (m, 1H), 3.40-3.33 (m, 1H), 2.82 (d, J=4 Hz, 3H), 1.60 (d, J=8 Hz, 3H), 1.16-1.03 (m, 2H), 0.95-0.75 (m, 2H); LC-MS (ESI) m/z 420.1 [M+H]+.

Provenance & Evidence