Hydrochloric Acid → HCID 131736557, compound

Participants

Reaction Steps

4-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-5-fluoro-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (133 mg, 0.21 mmol) was added into a mixture of a 4N solution of HCl in dioxane (2 mL, 8.0 mmol) and water (0.4 mL). After 1 hour of stirring at RT, the reaction mixture was diluted with a 1N aqueous solution of NaOH (15 mL) and extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum. After purification by flash chromatography (silica, DCM/EtOH/28% aqueous ammonia), the parent compound was obtained as a white solid. The solid was dissolved in DCM (2 ml), then a 2N solution of HCl in Et2O (0.5 mL) was added, followed by Et2O (2 mL). The precipitate was filtered off, washed with Et2O (3×) and dried under vacuum to give the title compound as a white powder (34 mg, 32%). 1H NMR (D2O) δ 7.76-7.67 (m, 1H), 7.47-7.34 (m, 2H), 5.01 (s, 1H), 4.98 (s, 1H), 4.72 (s, 1H), 4.67 (s, 1H), 4.15 (s, 2H), 3.40-3.21 (m, 8H), 2.80 (s, 1.5H), 2.76 (s, 1.5H), 2.63 (s, 1.5H), 2.57 (s, 1.5H). HPLC (max plot) 99.9%, Rt 2.39 min. UPLC/MS: (MS+) 443.4 ([M+H]+), (MS−) 441.4 ([M−H]−).

Provenance & Evidence