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

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.

1. customprepared
2. temperaturethe resulting suspension was heated at 80-85° C. for 1.5 h
3. temperatureOn cooling to room temperature
4. customThe organic layer was collected
5. washwashed with brine, sat. Sodium bicarbonate solution, brine
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by column chromatography on silica gel using
10. additiona solvent mixture of dichloromethane and methanol (95/5 and 9/1)

ORDレコード

ord-1e401faa793449069b19165d8540c6b3

出典データセット

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06468977B1