HCID 118598561, compound → HCID 118599084, compound

Participants

Reaction Steps

To a solution of 6′-bromo-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-c]pyridine]-1′,5′-dione (2, 0.3 g, 0.96 mmol) in tetrahydrofuran (25 mL), n-butyllithium (0.58 g, 2.89 mmol) was added at −78° C. The reaction mixture was stirred for 30 min. To the mixture N-methoxy-N-methylpyrimidine-4-carboxamide (1, 0.25 g, 1.44 mmol) was added at −78° C. and then the mixture was stirred at room temperature for 16 h. After completion, the reaction was quenched with aqueous solution of ammonium chloride (50 mL) and extracted with dichloromethane (2×50 mL). The organic layer was separated and was hed with brine (25 mL) and the solvent was evaporated under reduced pressure. The crude was purified by silica gel (220-400 mesh) column chromatography using 0.5% methanol in dichloromethane as eluent. The fractions were concentrated to afford 8′-methyl-6′-(pyrimidine-4-carbonyl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione as yellow solid. Yield: 0.001 g, 3.0%; MS (ESI) m/z 339.13 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 10.58 (s, 1H), 9.26 (s, 1H), 9.07 (d, J=5.08 Hz, 1H), 9.97 (s, 1H), 7.83 (d, J=5.2 Hz, 1H), 2.85-2.75 (m, 2H), 2.45 (s, 3H), 1.68-162 (m, 2H), 1.60-1.53 (m, 3H), 1.46-1.43 (m, 2H), 1.10-1.09 (m, 1H).

Provenance & Evidence