Hydrochloric Acid → HCID 122429367, compound

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Reaction Steps

A solution of (S)-4-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-5-fluoro-phenoxy]-azepane-1-carboxylic acid tert-butyl ester (180 mg; 1.11 mmol; 1 eq.) in a 4M solution of HCl in 1,4-dioxane (2 mL) was stirred at room temperature for 16 hours. The residue was diluted with 0.1M NaOH and extracted with DCM (2×). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (38 mg, 7%) as a yellow solid. 1H NMR (DMSO-d6) δ 8.34 (s, 1H), 7.37 (ddd, J=8.5, 6.8, 3.2 Hz, 1H), 7.12 (dd, J=11.7, 2.3 Hz, 1H), 6.88 (td, J=8.4, 2.3 Hz, 1H), 4.93-4.72 (m, 3H), 4.54 (d, J=15.1 Hz, 2H), 3.03-2.75 (m, 6.7H), 2.62 (s, 1.5H), 2.56 (s, 1.5H), 2.11-1.49 (m, 6.3H). HPLC (max plot) 90.3%, Rt 2.91 min. UPLC/MS: (MS+) 458.4 ([M+H]+).

Provenance & Evidence