2-(Dimethylamino)acetohydrazide → HCID 178483334, compound

Participants

Reaction Steps

The title compound was prepared according to the procedure of Example 367 C using N-cyclopropyl(3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl)carboxamide.2HCl (377 mg, 0.89 mmol), N-amino-2-(dimethylamino) acetamide (315 mg, 2.69 mmol) and sodium methoxide (515 μL of a 25% w/w in methanol) in anhydrous methanol (5.0 mL) with a reaction time of 24 h. Purification of the residue by flash chromatography on silica gel with 50% methanol in ethyl acetate gave the desired product as a light orange solid. Further purification by preparatory TLC using 50% methanol in ethyl acetate afforded the title compound (145 mg, 40% yield) as an off-white powder. 1H NMR (DMSO-d6) δ 8.8 (br d, 1H), 8.7 (s, 1H), 8.4 (s, 1H), 8.14-8.05 (m, 2H), 7.84 (d, 1H), 7.7-7.6 (m, 2H), 3.55 (s, 2H), 2.92-2.85 (m, 1H), 2.2 (s, 6H); ES-MS (m/z) 402 [M+H]+.

Provenance & Evidence