1,2-Dichloroethane → HCID 178449063, compound

Participants

Reaction Steps

To 1H-pyrazole-3-carboxylic acid (Matrix, 350 mg, 3.12 mmol) in DMF (8.7 mL) were added EDC (658 mg, 3.43 mmol), HOBT (622 mg, 4.06 mmol), i-Pr2EtN (1.6 mL, 9.37 mmol) and n-butylamine (550 μL, 3.28 mmol). The resulting solution was stirred at room temperature overnight. The reaction mixture was then quenched with sat. aq. NH4Cl solution, washed with 1N aq. HCl solution and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified using flash column chromatography (gradient from 0% to 5% (MeOH/CH2Cl2) to give the title compound (530 mg, 76%) as a colorless crystalline solid. 1H NMR (CD3OD, 1.5:1 mixture of amide rotamers) δ 7.74 (br s, 1H), 6.67 (br s, 1H), 6.38 (br s, 1H), 3.70-3.39 (m, 4H), 1.64 (quin, J=7.6 Hz, 4H), 1.36 (dt, J=14.4, 7.0 Hz, 4H), 1.04-0.88 (m, 6H); MS(ESI+) m/z 224.3 (M+H)+.

Provenance & Evidence