Pyridine → HCID 178432776, compound

Participants

Reaction Steps

A solution of trans-5-chloro-N-(4-hydroxymethyl-cyclohexyl)-2-methyl-nicotinamide (Intermediate E, step 2) (100 mg, 0.354 mmol) and pyridine (3.6 ml) in dry DCM (3.5 ml) under nitrogen was cooled to approx. 0° C. using an ice-water bath. Methanesulfonyl chloride (0.030 ml, 0.389 mmol) was added dropwise. The reaction mixture was allowed to warm to room temp and stirred at this temp for 4 hours. The reaction was quenched by the addition of sat. NH4Cl at room temp and then extracted with diethyl ether (3×20 ml). The Et2O extracts were combined, washed with sat brine (20 ml), dried (MgSO4), filtered and evaporated to give the title compound as a colourless solid. LCMS 361.2/363.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.52 (1H, d), 7.65 (1H, d), 5.68 (1H, br d), 4.09 (2H, d), 3.96 (1H, m), 3.04 (3H, s), 2.65 (3H, s), 2.21 (2H, m), 1.96 (2H, m), 1.79 (1H, m), 1.27 (4H, m).

Provenance & Evidence