Acetic Acid → HCID 71622962, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (90 mg; 0.42 mmol; 4 eq.) was added to a solution of (6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-[2-(pyrrolidin-3-ylmethoxy)-phenyl]-methanone formic acid salt (50 mg; 0.11 mmol; 1 eq.), acetone (47 μL; 0.64 mmol; 6 eq.) and AcOH (7 μL; 0.13 mmol; 1.2 eq.) in DCM (3 mL) and the reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with DCM, washed with sat. aq. NaHCO3, dried over sodium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (47 mg, 76%) as a white solid. 1H NMR (CDCl3) δ 7.44-7.30 (m, 2H), 7.12-6.98 (m, 1H), 6.98-6.87 (m, 1H), 5.07-4.92 (m, 2H), 4.63 (br s, 2H), 4.09-3.86 (m, 2H), 2.88 (d, J=18.2 Hz, 4H), 2.65 (d, J=23.0 Hz, 5H), 2.50-2.05 (m, 3H), 2.04-1.84 (m, 1H), 1.58 (dt, J=13.2, 5.8 Hz, 1H), 1.02-0.81 (m, 6H). HPLC (max plot) 94.3%, Rt 2.92 min. UPLC/MS: (MS+) 468.5 ([M+H]+).

Provenance & Evidence