Triethylamine → HCID 59489563, compound

Participants

Reaction Steps

To a solution of 2-[1-(2-amino-ethyl)-1H-pyrazol-3-yl]-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide (0.1 g, 0.29 mmol) in methylene chloride (5 mL) was added 4-fluoro-benzoyl chloride (0.07 mL, 0.44 mmol) and triethyl amine (0.08 mL, 0.58 mmol). The reaction mixture was stirred under nitrogen at room temperature for 16 hr. The reaction mixture was diluted with methylene chloride (50 mL), water (100 mL) and brine (100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (hexanes:ethyl acetate, 1:1) to provide 2-{1-[2-(4-fluoro-benzoylamino)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide as a white solid (0.56 g, 43%). 1H NMR (400 MHz, CDCl3) δ 8.63 (bs, 1H), 8.57 (d, J=4 Hz, 1H), 7.70-7.81 (m, 3H), 7.46 (d, J=2 Hz, 1H), 7.29-7.33 (m, 1H), 7.09 (t, J=8 Hz, 2H), 6.84 (d, J=2 Hz, 1H), 6.84-6.88 (m, 1H), 6.10-6.15 (bm, 1H), 4.65 (d, J=4 Hz, 2H), 4.42 (bt, J=5 Hz, 2H), 3.89-3.97 (m, 2H), 2.75 (s, 3H); MS (M+H)+=464.8; Rt=1.04 min; HRMS (M+H)+=465.15.

Provenance & Evidence