Triethylamine → 2-(3-Methoxy-[1,2,4]thiadiazol-5-ylamino)-acetamide

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Reaction Steps

To a suspension of glycinamide hydrochloride (0.55 g, 5 mmol) in DMF (10 mL) was added triethylamine (1.7 mL, 12 mmol) and the resulting mixture was stirred for 15 min at room temperature. This was added to a solution of 5-chloro-3-methoxy-[1,2,4]thiadiazole (0.38 g, 2.5 mmol, prepared according to the procedure by Goerdeler, J. et al. in Chem. Ber. 1955, 88, 843) in DMF (15 mL). Then, tetra-butylammonium bromide (50 mg) was added and the resulting suspension was heated at 80-85° C. for 1.5 h. On cooling to room temperature, the reaction mixture was diluted with water and ethyl acetate. The organic layer was collected, washed with brine, sat. Sodium bicarbonate solution, brine, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by column chromatography on silica gel using a solvent mixture of dichloromethane and methanol (95/5 and 9/1) afforded 2-(3-methoxy-[1,2,4]thiadiazol-5-ylamino)-acetamide (75 mg, 16%) as a white solid. 1H-NMR (MeOD) δ 4.03 (s, 2H, NCH2), 3.94 (s, 3H, OMe); 13C-NMR (MeOD) δ 182.0, 173.3, 170.0, 56.7 (MeO), 47.9; MS (m/z) 189 (M++1), 172, 144, 87.

Provenance & Evidence