Triethylamine → 1-[3-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-2H-pyrazolo[3,4-c]pyridin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

Participants

Reaction Conditions

Reaction Steps

7-Chloro-3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-2H-pyrazolo[3,4-c]pyridine (I-1A-1c; 71 mg, 0.17 mmol), 4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1f; 62 mg, 0.36 mmol) and triethylamine (52 microliters, 0.52 mmol) were combined in ethanol (1.2 ml) and the heterogeneous mixture was stirred and heated to 60° C. After 3 days, the reaction was cooled to room temperature and purified on a Biotage™ Flash 12M column using a solvent gradient of 0-2-4-6% methanol in methylene chloride as eluant to afford title compound I-1A-1 (73 mg, 78%) as a glass: +ESI MS (M+1) 543.1; 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=2.1 Hz, 1H), 7.60 (d, J=8.7 Hz, 1H), 7.57 (d, J=6.2 Hz, 1H), 7.49 (dd, J=8.3, 2.1 Hz, 1H), 7.38 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.3 Hz, 2H), 6.84 (d, J=6.2 Hz, 1H), 4.35-4.28 (m, 2H), 4.10 (ddd, J=13.3, 9.1, 3.3 Hz, 2H), 2.51 (q, J=7.1 Hz, 2H), 2.12 (ddd, J=13.7, 9.1, 3.7 Hz, 2H), 1.73 (dq, J=13.3, 3.3 Hz, 2H), 1.10 (t, J=7.1 Hz, 3H).

Provenance & Evidence