Water → HCID 67962963, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium perborate tetrahydrate (95%, 3.12 g, 19.3 mmol) and trifluoroacetic acid (10 mL) was heated to 75° C. To this was added a solution of ethyl 3-amino-5-benzyl-1-methyl-1H-pyrazole-4-carboxylate (prepared according to the method of Y. Xia et al., J. Med. Chem. 1997, 40, 4372-4377; 1.00 g, 3.86 mmol) in trifluoroacetic acid, and the mixture was allowed to react at 75° C. for 2.5 hours. The reaction was then cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo; purification via silica gel chromatography (Eluant: 30% EtOAc in heptane) provided C20 as a dark yellow oil. Yield: 333 mg, 1.15 mmol, 30%. LCMS m/z 290.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.32 (t, J=7.1 Hz, 3H), 3.74 (s, 3H), 4.33 (br s, 2H), 4.34 (q, J=7.1 Hz, 2H), 7.14-7.18 (m, 2H), 7.25-7.30 (m, 1H), 7.31-7.36 (m, 2H).

Provenance & Evidence