2'-Methoxyacetophenone → HCID 178489295, compound

Participants

Reaction Steps

DIPEA (99 mg, 0.76 mmol) was added to a stirred solution {[5-(2-methoxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (60 mg, 0.22 mmol) (prepared by the method used for the synthesis of Intermediate 30, starting from (2′-methoxy)acetophenone) in DMF (2.0 mL) followed by HOBt (34 mg, 0.25 mmol) and EDCI.HCl (49 mg, 0.25 mmol). After 2 minutes of stirring, (2-chloro-phenyl)-piperidin-4-yl-amine dihydrochloride (54 mg, 0.22 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine and concentrated. The residue was purified washing with diethyl ether to afford 67 mg (43.5% Yield) of 5-(2-methoxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 468.2, 98.33%. 1H NMR (300 MHz, DMSO-d6): δ13.6 (S, 1H), 8.05 (m, 1H), 7.7 (m, 1H), 7.35 (m, 1H), 7.24 (m, 1H), 7.12 (m, 2H), 7.0 (m, 2H), 6.82 (m, 1H), 4.85 (d, 1H), 4.3 (d, 1H), 4.1 (d, 2H), 3.9 (s, 3H), 3.85 (m, 1H), 3.6 (m, 1H), 3.1 (m, 1H), 2.7 (m, 1H), 1.9 (m, 2H), 1.4 (m, 2H).

Provenance & Evidence