Dimethylformamide → HCID 66906056, compound

Participants

Reaction Steps

A stirred solution of (R)-1-(6-(4-cyanophenyl)benzo[d]thiazol-2-yl)pyrrolidin-3-yl methanesulfonate (Reference Example 14b, 20 mg, 0.050 mmol), 2-methylpiperidine (0.029 mL, 0.25 mmol), and N,N-dimethylformamide (0.01 mL) in isopropanol (0.50 mL) was heated at 150° C. under microwave irradiation for 15 minutes. The reaction mixture was cooled to room temperature, concentrated, and purified by silica gel chromatography (100:0 to 70:30 dichloromethane/ethyl acetate, then 98:2 to 92:8 dichloromethane/methanol). Fractions containing product were combined and concentrated under reduced pressure to give 4-(2-435)-3-(2-methylpiperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazol-6-yl)benzonitrile. 1H NMR (300 MHz, CD2Cl2) δ ppm 1.06-1.12 (m, 3H), 1.37-1.45 (m, 2H), 1.54-1.61 (m, 1H), 1.67-1.77 (m, 2H), 2.01-2.16 (m, 2H), 2.19-2.29 (m, 1H), 2.35-2.51 (m, 1H), 2.63-2.70 (m, 1H), 2.81-2.95 (m, 1H), 3.36-3.50 (m, 1H), 3.50-3.79 (m, 5H), 7.55 (s, 2H), 7.72 (s, 4H), 7.88 (s, 1H); MS (ESI) m/z 403 (M+H)+.

Provenance & Evidence