1,3,4-Thiadiazole-2-carboxamide, 5-amino-N-methyl- synthesis

Yield:-

Reaction Conditions:

in methanol;ethanol at 20 - 70;

Steps:

45; 46

To a suspension of ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate (106 mg, 0.612 mmol) in methanol (1.5 mL) was added 33 wt % ethanol solution of methylamine (0.5 mL, 4.00 mmol). The mixture was stirred at room temperature for 6 h, heated to 70 ⁰C and cooled. The mixture was concentrated, mixed with water and lyophilized to give 5-amino-N-methyl-l,3,4-thiadiazole-2-carboxamide as a white solid (99 mg). ¹H NMR (400 MHz, DMSO-d6) δ ppm 8.69 (q, J=4.8 Hz, 1 H), 7.70 (s, 2 H) 2.73 (d, J=4.78 Hz, 3 H); MS (ES+) m/z: 159 (M+H); LC retention time: 0.44 min (analytical HPLC Method A).

References:

WO2009/100171,2009,A1 Location in patent:Page/Page column 105-106