Isopropylamine → HCID 178457832, compound

Participants

Reaction Conditions

Reaction Steps

trans-4-(2-Chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylic acid hydrochloride (0.500 g, 1.487 mmol) was suspended in THF (3 mL). Thionyl chloride (0.434 mL, 5.95 mmol) was added to the suspension, and the reaction mixture was stirred at 20° C. for 2 hours. The resulting mixture was concentrated in vacuo. The solid was resuspended in THF (5 mL) and then propan-2-amine (0.153 mL, 1.785 mmol) was added. The mixture was stirred at RT for 16 hours, and additional propan-2-amine (0.128 mL, 1.487 mmol) was added. Stirring at RT was continued for 1 hour. The reaction mixture was diluted with DCM and washed with saturated aqueous NaHCO3 and brine. The organic layer was concentrated in vacuo, and the residual material was purified via silica gel chromatography, eluting with 20-100% EtOAc in hexanes, to yield trans-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide as a yellow solid (0.312 g, 61.6% yield). MS m/z=341.0 [M+H], calc 340.81 for C15H21ClN4O3.

Provenance & Evidence