2-amino-N-cyclopropylacetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methylpyridine-3-carbodithioate (2.97 g, 17.52 mmol) in methanol (10 mL) was added a solution of 2-amino-N-cyclopropylacetamide (2 g, 17.52 mmol) (HCl salt) and triethylamine (3.55 g, 35.0 mmol). The mixture was stirred at room temperature for 1 hour and then diluted with ethyl acetate and washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered, and concentrated in vacuo to give N-cyclopropyl-2-(pyridine-3-carbothioamido)acetamide as a yellow solid (3.60 g, 83%): mp 152-153° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.60 (s, 1H), 8.91 (ddd, J=7.0, 2.3, 0.7 Hz, 1H), 8.76-8.56 (m, 1H), 8.10 (m, 2H), 7.57-7.32 (m, 1H), 4.26 (m, 2H), 2.73-2.57 (m, 1H), 0.77-0.61 (m, 2H), 0.50-0.29 (m, 2H); ESIMS (m/z) 234 ([M−H]−). washed with saturated aqueous NaHCO3, brine dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-cyclopropylglycinamide (1.22 g) (J. Med. Chem. 2005, 48, 7808-7820) in ethanol (12 mL) was added 4-thioxo-1,3-thiazolidin-2-one (1.42 g), and the mixture was stirred at room temperature for 5 hr. The precipitate was collected by filtration, and the solid was washed with ethanol to give the title compound (2.0 g). The precipitate was collected by filtration the solid was washed with ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methylpyridine-3-carbodithioate (2.97 g, 17.52 mmol) in methanol (10 mL) was added a solution of 2-amino-N-cyclopropylacetamide (2 g, 17.52 mmol) (HCl salt) and triethylamine (3.55 g, 35.0 mmol). The mixture was stirred at room temperature for 1 hour and then diluted with ethyl acetate and washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered, and concentrated in vacuo to give N-cyclopropyl-2-(pyridine-3-carbothioamido)acetamide as a yellow solid (3.60 g, 83%): mp 152-153° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.60 (s, 1H), 8.91 (ddd, J=7.0, 2.3, 0.7 Hz, 1H), 8.76-8.56 (m, 1H), 8.10 (m, 2H), 7.57-7.32 (m, 1H), 4.26 (m, 2H), 2.73-2.57 (m, 1H), 0.77-0.61 (m, 2H), 0.50-0.29 (m, 2H); ESIMS (m/z) 234 ([M−H]−). washed with saturated aqueous NaHCO3, brine dried over MgSO4 filtered concentrated in vacuo