3-Methyl-3-phenylbutanoyl chloride → N-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-2-yl]-3-methyl-3-phenylbutanamide

Participants

Reaction Steps

To the product from Example 117A (82 mg, 0.42 mmol) was added a solution of the product from Example 99A (59 mg, 0.2 mmol) in pyridine (2.0 mL). The mixture was stirred at ambient temperature for 1 hour and then at 40° C. for 1 hour. The reaction mixture was concentrated under vacuum and purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 30-100% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.13-10.16 (bs, 1H), 9.09 (dd, J=7.0, 1.7 Hz, 1H), 8.60 (dd, J=4.1, 1.7 Hz, 1H), 7.68-7.72 (m, 2H), 7.40-7.45 (m, 4H), 7.27-7.35 (m, 2H), 7.15-7.22 (m, 1H), 7.12 (dd, J=7.0, 4.1 Hz, 1H), 2.70 (s, 2H), 1.41 (s, 6H); MS (ESI) m/z 405 (M+H)+; Anal. calculated for C23H21ClN4O.0.1H2O: C, 67.93; H, 5.25; N, 13.78. Found C, 67.65; H, 5.08; N, 13.61.

Provenance & Evidence