Hydrochloric Acid → HCID 131736546, compound

Participants

Reaction Steps

HCl (2.64 mL) was added to a solution of (S)-3-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-5-fluoro-phenoxy]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.4 g; 2.64 mmol; 1 eq.) in 1,4-dioxane (10 mL) and the reaction mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was taken up in DCM, washed with 0.1M NaOH, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (48 mg, 4%) as a yellow solid. 1H NMR (DMSO-d6) δ 8.28 (s, 1H), 7.44-7.33 (m, 1H), 7.17-7.09 (m, 1H), 6.91 (td, J=8.4, 2.3 Hz, 1H), 5.14-5.06 (m, 1H), 4.86-4.78 (m, 2H), 4.63-4.42 (m, 2H), 3.35-3.21 (m, 1H), 3.08-2.85 (m, 3H), 2.83 (s, 1.5H), 2.80 (s, 1.5H), 2.61 (s, 1.5H), 2.55 (s, 1.5H), 2.16-1.97 (m, 1H), 1.95-1.83 (m, 1H). HPLC (max plot) 93.3%, Rt 2.67 min. UPLC/MS: (MS+) 430.4 ([M+H]+).

Provenance & Evidence