2-Fluoro-4-(trifluoromethyl)benzoyl chloride → HCID 22346946, compound

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Reaction Steps

A mixture of tert-butyl 4-[4-amino-3-(4-amino-3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (0.10 g, 0.228 mmol) in dichloromethane (2 mL) and pyridine (1 mL) was treated with 2-fluoro-4-trifluoromethylbenzoyl chloride (0.057 g, 0.251 mmol) then stirred for 1 hour. The solvents were evaporated then the residue was treated with trifluoroacetic acid (1 mL) in dichloromethane (2 mL). The mixture was stirred for 1 hour at ambient temperature then the solvents were evaporated under reduced pressure and the residue purified by RP preparative HPLC on a C18 column using acetonitrile-0.05 M ammonium acetate as a mobile phase. Lyophilization afforded the pure title compound: 1H NMR (DMSO-d6, 400 MHz) δ 9.90 (d, 1H), 8.31 (d, 1H), 8.24 (s, 1H), 7.99 (t, 1H), 7.89 (d, 1H), 7.75 (d, 1H), 7.33 (s, 1H), 7.30 (d, 1H), 4.78 (m, 1H), 3.94 (s, 3H), 3.10 (m, 2H), 2.69 (m, 2H), 2.08 (m, 2H), 1.85-2.0 (m, 5H); RP-HPLC (Hypersil HS C18Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 17.33 min; MS: MH+ 530.2.

Provenance & Evidence