Hydrochloric Acid → HCID 131736567, compound

Participants

Reaction Steps

A 4M solution of HCl in 1,4-dioxane (4 mL; 16 mmol; 82 eq.) was added to a solution of 4-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-3-trifluoromethyl-piperidine-1-carboxylic acid tert-butyl ester (116 mg; 0.20 mmol; 1 eq.) in 1,4-dioxane (2 mL) and the reaction mixture was stirred at room temperature for 16 hours then concentrated in vacuo. Crystallization from cold iPrOH afforded the title compound (65 mg, 62%) as a white solid. 1H NMR (DMSO-d6) δ 9.14 (s, 2H), 7.48 (d, J=7.6 Hz, 1H), 7.44-7.34 (m, 1H), 7.30 (d, J=8.5 Hz, 1H), 7.15 (t, J=7.4 Hz, 1H), 5.23 (br s, 1H), 4.87 (d, J=6.3 Hz, 2H), 4.63-4.34 (m, 2H), 3.52-3.38 (m, 1H), 3.31-3.23 (m, 1H), 3.20-2.88 (m, 3H), 2.85 (s, 1.5H), 2.81 (s, 1.5H), 2.62 (s, 1.5H), 2.56 (s, 1.5H), 2.16-2.03 (m, 1H), 2.00-1.86 (m, 1H). HPLC (max plot) 96.5%, Rt 3.12 min. UPLC/MS: (MS+) 494.3 ([M+H]+).

Provenance & Evidence