Water → N2-(3-cyanomethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide

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Reaction Steps

To a solution of 3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarbonyl chloride (0.49 g, 1.34 mmol) in dichloromethane (4 mL) was added 3-cyanomethyl-2,4,6-trimethylaniline (0.24 g, 1.34 mmol) at 0° C. Triethylamine (0.21 mL, 1.47 mmol) and 4-dimethylaminopyridine (16 mg, 0.13 mmol) were added. The mixture was stirred at room temperature for 2 hours, then mixed with water (10 mL). The organic material was separated, and the aqueous layer was extracted with dichloromethane (2×5 mL). The extracts were combined and washed with water (10 mL) and saturated sodium chloride (10 mL), dried (MgSO4), then concentrated. The residue was purified by flash chromatography (SiO2, hexane:ethyl acetate/3:1, then 1:1) to give N2-(3-cyanomethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide (0.28 g, 41%) as a yellow oil.

Provenance & Evidence