HCID 89649744, compound → HCID 131736554, compound

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Reaction Steps

A solution of 3-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxymethyl]-azetidine-1-carboxylic acid tert-butyl ester (920 mg; 1.8 mmol; 1 eq.) in TFA (5 mL) and DCM (5 mL) was stirred at room temperature for 1 hour and then concentrated in vacuo. The residue was taken up in water, the pH made basic with 5M NaOH and extracted with DCM (2×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (10 mg, 1%) a yellow gum. 1H NMR (CDCl3) δ 10.56 (s, 1H), 8.82 (s, 1H), 7.50-7.40 (m, 2H), 7.15-7.02 (m, 2H), 5.09 (s, 0.6H), 5.05 (s, 1.4H), 4.83 (s, 1.4H), 4.70 (s, 0.6H), 4.43-4.27 (m, 3H), 3.93-3.78 (m, 1H), 3.21-3.09 (m, 1H), 3.03 (s, 2H), 2.92 (s, 1H), 2.79 (s, 2H), 2.78 (s, 1H). HPLC (max plot) 99.3%, Rt 2.65 min. UPLC/MS: (MS+) 412.4 ([M+H]+).

Provenance & Evidence