HCID 178457845, compound → HCID 178457844, compound

Participants

Reaction Steps

To a solution of cis-N-isopropyl-4-(2-morpholino-5-nitropyridin-4-ylamino)cyclohexanecarboxamide (121 mg, 0.309 mmol) in EtOH (5 mL) and EtOAc (3 mL) was added 10% palladium on carbon (32.9 mg, 0.031 mmol). The reaction was stirred under a hydrogen atmosphere (H2 balloon) at RT. After 3 hours, the reaction mixture was filtered through Celite® brand filter aid (washed with MeOH and DCM), and concentrated to afford cis-4-(5-amino-2-morpholinopyridin-4-ylamino)-N-isopropylcyclohexane-carboxamide as a dark oil. The diamine was dissolved in THF (3 mL), and 4-fluorobenzoyl isothiocyanate (61.8 mg, 0.341 mmol) was added. The reaction was stirred at 0° C. for 15 minutes, and then EDC (89 mg, 0.465 mmol) and DIPEA (0.081 mL, 0.465 mmol) were added. The reaction was stirred at 60° C. for 2 hours and then overnight at RT. After 16 hours, the reaction mixture was concentrated, and adsorbed onto a plug of silica gel. The residue was purified by column chromatography, eluting with 0-100% EtOAc in DCM, to provide (E)-4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-morpholino-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide as a light-yellow powder (38 mg, 24.11% yield). MS, m/z (C27H33FN6O3): calcd, 508.3. found, 509.1 [M+H].

Provenance & Evidence