Acetic Acid → HCID 67267101, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(4-Amino-2-methylphenyl)-2,2-dimethylpropionamide (300 mg, 1.45 mmol) and 5-(4-Chlorophenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (360 mg, 1.45 mmol) in acetonitrile (4 mL) was heated and stirred at 170° C. under microwave irradiation for 20 minutes. The obtained reaction mixture was added carefully into solution of sodium cyanoborohydride (0.36 g) in methanol followed by acetic acid (1 mL). After 60 minutes it was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution and the organic layer was evaporated. The title compound was separated by flash chromatography on SiO2 with gradient heptane-ethyl acetate and then precipitated from ethyl acetate with heptane. Yield 112 mg, 18%. LC/MS-TOF (m/z) 441; RT=2.34, (UV, ELSD) 98%, 100%. 1H NMR (DMSO-d6): 1.18 (s, 9H), 1.96 (s, 3H), 2.15 (s, 3H), 3.47 (s, 3H), 3.75 (d, 2H), 5.4 (t, 1H, NH), 6.29 (dd, 1H), 6.33 (d, 1H), 6.24 (d, 1H), 6.99 (d, 2H), 7.41 (d, 2H), 8.58 (s, 1H, NH).

Provenance & Evidence