Methyl iodide → HCID 67276238, compound

Participants

Reaction Steps

Methyl iodide (263 μL, 4.2 mmol) and 2,4-dichloro-N-[{4-[(cyclopropylmethyl)sulphonyl]phenyl}(pyridin-3-yl)methyl]benzamide (prepared as described in Example 53, 200 mg, 0.42 mmol) were stirred in acetone (4 mL) for 16 h under nitrogen. The resulting yellow suspension was concentrated in vacuo to give 3-{{4-[(cyclopropylmethyl)sulphonyl]phenyl}[(2,4-dichlorobenzoyl)amino]methyl}-1-methylpyridinium iodide. The salt was dissolved in methanol (5 mL) and the solution cooled to −10° C. Sodium borohydride (18 mg, 0.47 mmol) was added and the mixture was stirred at −10° C. for 10 mins and then allowed to warm to room temperature, with stirring, over 1 h. The reaction was quenched with 1N NaOH(aq) (20 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated. Purification by chromatography on silica eluting with 5% methanol in dichloromethane (+<0.5% ammonia) was followed by salt formation by treatment with ethereal HCl to give the title compound as a white solid (123 mg, 55% yield). m/z (ES+) 495 (M+H), 493 (M+H).

Provenance & Evidence