Methanamine, N-methoxy-, hydrochloride (1:1) → 2,6-Dichloro-N-methoxy-N-methylisonicotinamide

Participants

Reaction Steps

HATU (1.97 g, 5.20 mmol), HOAT (707 mg, 5.20 mmol) and DIEA (1.77 ml, 10.5 mmol) were added to 2,6-dichloroisonicotinic acid (1 g, 5.20 mmol) in anhydrous DMF (5 ml). The mixture was stirred for 5 minutes, then N-methyl methoxylamine hydrochloride (507 mg, 5.20 mmol) was added in one portion followed by DIEA (800 μl, 5.2 mmol). The reaction was stirred for 30 minutes, then the crude product was partitioned between EtOAc (50 ml) and water (50 ml) and the organic level washed with water (3×50 ml). The organic phase was dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography eluting with EtOAc:n-hexanes (2:3) to afford the title compound (1.12 g).

Provenance & Evidence