Hydrazinecarboxylic acid, ethyl ester → HCID 136597019, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl trans-3-((3-cyanoisoquinolin-1-yl)oxy)-4-methylpyrrolidine-1-carboxylate (790 mg, 2.235 mmol), ethyl hydrazinecarboxylate (1164 mg, 11.18 mmol) and DBU (168 μL, 1.118 mmol) in N-methyl-2-pyrrolidinone (5.6 mL) and under a nitrogen atmosphere was heated at 170° C. in a sealed vial for 16 hours. The reaction mixture was allowed to cool to RT and was poured onto ice water, forming a pale yellow precipitate. After the ice melted (total volume was 100 mL) the solid was filtered and dried to give the title compound as a pale yellow solid (647 mg, 70.3%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.12 (d, 3H), 1.40 (d, 9H), 3.11 (d, 1H), 3.70 (dd, 2H), 3.86-4.04 (m, 2H), 5.70-5.80 (1H, m), 7.68 (t, 1H), 7.81 (t, 1H), 7.98 (s, 1H), 8.02 (d, 1H), 8.18 (d, 1H), 11.79 (s, 1H), 12.03 (d, 1H); ESI-MS m/z [M+H-Boc]+ 312.7.

Provenance & Evidence