Diisopropylethylamine → HCID 57964912, compound

Participants

Reaction Steps

To a stirred mixture of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 27; 60 mg, 0.123 mmol) and N,N-diisopropylethylamine (0.11 mL, 0.615 mmol) in dichloromethane (1.0 mL) at room temperature was added 4-methylvaleroyl chloride (Pfaltz & Bauer, Inc., Waterbury, Conn., USA; 20 mg; 0.15 mmol). After 1 h, the mixture was washed with 1 N HCl followed by water. The organic layer was dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was triturated with diethyl ether, filtered, washed with diethyl ether and allowed to air dry to provide 1-{4-[4-(4-Methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-4-methyl-pentan-1-one (32 mg, 55%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 0.87 (d, 6H, J=6.6 Hz), 1.36-1.44 (m, 2H), 1.50-1.59 (m, 1H), 1.94-2.10 (m, 4H), 2.33-2.38 (m, 2H), 2.74-2.86 (m, 1H), 3.30 (water peak and SO2CH3), 3.98-4.08 (m, 1H), 4.46-4.57 (m, 1H), 5.00-5.14 (m, 1H), 7.62 (d, 2H, J=8.5 Hz), 8.04 (d, 2H, J=8.7 Hz), 8.38 (s, 1H), 8.55 (s, 1H). Mass spectrum MH+=472.

Provenance & Evidence