N-Methylcyclohexylamine → HCID 13987626, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 1-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-4-piperidinecarboxylic acid (3.12 g, 10 mmol) and N-cyclohexyl-N-methylamine (1.36 g, 12 mmol) were combined in dimethylformamide (200 mL) and cooled to -20° C. Triethylamine (2.91 mL, 21 mmol) and diphenylphosphoryl azide (2.59 mL, 12 mmol) were added, the mixture stirred at -20° C. for 3 hours, and allowed to warm to room temperature. After 18 hours, the mixture was diluted with CH2Cl2 (200 mL), scratched to initiate crystallization, and stirred for an additional 72 hours. The resultant precipitate was collected, washed with CH2Cl2, and dried to give 2.09 g of a pale yellow solid (51%). Crystallization from dimethylformamide (80 mL) gave 1.02 g of pale yellow crystals, m.p. 318°-321° C.

Provenance & Evidence