Potassium Hydroxide → HCID 178509159, compound

Participants

Reaction Conditions

Reaction Steps

1-[({5-Amino-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylmethyl}carbamoyl)-methyl]pyrrolidine-2-carboxylic acid methyl ester (80 mg, 0.20 mmole) was dissolved in 1.5 mL of 95% ethanol with KOH (19.7 mg (85%), 0.29 mmole). The solution was heated at 76° C. for 1 hour. The reaction was quenched by the addition of 1 mL of water and then acidified to pH 3 with 1.5 M HCl. The solution was evaporated to dryness together with 2-PrOH and silica gel. The resulting powder was then placed onto a silica gel column. The crude material was purified by column chromatography (CH2Cl2:MeOH:H2O:HOAc=240:60:4.7:2.2) to yield 70 mg of the title compound as a yellow powder. MS (m/z, ES−): 388 (M−1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 8.77 (br s, 1H), 7.35-7.60 (m, 3H), 7.09 (m, 1H), 6.99 (br s, 2H), 4.50 (m, 2H), 3.31 (m, 1H), 3.01 (m, 2H), 2.29 (m, 1H), 2.05 (m, 1H), 1.93 (m, 1H), 1.72 (m, 1H), 1.50-1.61 (m, 2H).

Provenance & Evidence