1,2-Dichloroethane → HCID 178457814, compound

Participants

Reaction Conditions

Reaction Steps

A solution of cis-4-(5-Amino-2-(methylsulfonyl)pyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (0.069 g, 0.195 mmol) in THF (0.5 mL) was cooled to 0° C. and 4-fluorobenzoyl isothiocyanate (0.053 g, 0.292 mmol) was added as a THF solution. The mixture was stirred at 0° C. for 30 minutes and then was warmed to 20° C. and stirred for 1 hour. To the mixture was added DIPEA (0.051 mL, 0.292 mmol) and EDC (0.056 g, 0.292 mmol), and the reaction was heated at 60° C. for 1 hour. The reaction mixture was diluted with DCM and then washed with water and brine. The organic layer was concentrated under vacuum. The sample was purified by flash chromatography, eluting with 0-70% 90/10/1 DCM/MeOH/NH4OH:DCM to afford impure product as a light yellow solid. The impure material was further purified by preparative TLC, eluting with 90/10/1 DCM/MeOH/NH4OH:DCM to afford (E)-4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(methylsulfonyl)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide as a pale yellow solid (0.046 g, 47.1% yield). MS, m/z (C24H28FN5O4S); Calcd, 501.58. found 502.2 [M+H].

Provenance & Evidence