Lithium Hydroxide → HCID 59264675, compound

Participants

Reaction Steps

5-Methyl-1-[4-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-1H-pyrazole-4-carboxylic acid ethyl ester from Example 56 (270 mg, 0.66 mmole) is hydrolysed using lithium hydroxide in aqueous methanol and the resulting lithium salt recovered by freeze drying. The lithium salt, pyrrolidine (140 mg, 2 mmole), TBTU (325 mg, 1 mmole) and triethylamine (212 mg, 2 mmole) are dissolved in dimethylformamide (10 mL) and the mixture is stirred for 18 hours. The reaction is diluted with water, extracted with ethyl acetate, washed with water, dried and evaporated to dryness. The product is purified by chromatography on silica gel using 10% methanol in dichloromethane and the title compound recovered by crystallization from ethyl acetate. MS (m/e): 436.3 (M+1).

Provenance & Evidence