Water → HCID 68685023, compound

Participants

Reaction Steps

A solution of N-(4-cyclopropylmethanesulfonyl-1-cyclopropylmethylcyclohexylmethyl)-2-methylsulfanyl-6-trifluoromethylnicotinamide (44 mg, 0.087 mmol) in acetone (2 ml) was treated with a solution of oxone (161 mg, 0.26 mmol) in water (2 ml) and the mixture heated under reflux for 2 hours. The mixture was allowed to cool to ambient temperature and the pH of the mixture adjusted to 7 by the addition of saturated sodium hydrogen carbonate solution. The mixture was diluted with water (5 ml) and extracted with dichloromethane (5 ml). The mixture was separated using a 5 micron PTFE frit and the filtrate was evaporated. The colourless oil was purified by preparative plate chromatography on silica eluting with 10% ethyl acetate in dichloromethane. Collecting the appropriate band, trituration of the silica with ethyl acetate, filtration and evaporation gave a white foam (36 mg, 80%). 1H NMR δ (ppm)(CDCl3): 8.47 (1H, d, J=8.0 Hz), 7.98 (1H, d, J=8.0 Hz), 7.06 (1H, s), 3.65 (2H, d, J=6.0 Hz), 3.48 (3H, s), 2.94-2.89 (3H, m), 2.06-1.91 (6H, m), 1.41-1.35 (2H, m), 1.30 (2H, d, J=6.7 Hz), 1.22-1.15 (1H, m), 0.76-0.66 (3H, m), 0.49-0.41 (4H, m), 0.07 (2H, q, J=4.9 Hz). MS (m/e)=5.37.

Provenance & Evidence