4-Cyanobenzenesulfonyl chloride → HCID 59095495, compound

Participants

Reaction Steps

A mixture of 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.026 g, 0.08 mmol), 4-cyanobenzenesulfonyl chloride (0.019 g, 0.10 mmol) and pyridine (0.40 ml) was stirred at room temperature overnight. Most of pyridine was removed under reduced pressure and the residue was purified by preparative RP-HPLC (Rainin C18, 8 μm, 300 A, 25 cm; 25%-100% acetonitrile-0.1M ammonium acetate over 25 min, 21 ml/min) to give N1-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxy-phenyl]-4-cyano-1-benzenesulfonamide as yellow solids (0.018 g, 0.04 mmol): 1H NMR (DMSO-d6, 400 MHz) δ 9.91 (s, 1H), 8.13 (s, 1H), 8.05 (d, 2H), 7.89 (d, 2H), 7.44 (s, 1H), 7.27 (d, 1H), 7.00 (dd, 1H), 6.98 (d, 1H), 6.07 (broad, 2H), 5.07 (m, 1H), 3.49 (s, 3H), 2.11 (m, 2H), 1.88 (m, 4H), 1.69 (m, 2H); MH+489; TLC (ethyl acetate/methanol=9:1) Rf 0.49; RP-HPLC (Hypersil C18, 5 μm, 200 A, 25 cm; 25%-100% acetonitrile-0.1M ammonium acetate over 25 min, 1 ml/min) Rt 14.65 min.

Provenance & Evidence