4-Methylmorpholine → HCID 18712865, compound

Participants

Reaction Conditions

Reaction Steps

Sodium 1,1-dimethylethyl 4-(8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(S)-yl)-2(R)-carboxy-1-piperazinecarboxylate (prepared as described in Preparative Example 6 (sodium salt)) (0.5239 g, 1.09 mmoles), 2-[2-(1H-imidazol-1-yl)ethyl]piperidine (prepared as described in Preparative Example 57, Step D) (0.2544 g, 1.42 mmoles), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.272 g, 1.42 mmoles), 1-hydroxybenzotriazole (0.1918 g, 1.42 mmoles) and 4-methylmorpholine (0.156mL, 1.42 mmoles) were dissolved in anhydrous DMF (23.5 mL) and the mixture was stirred under argon at 25° C. for 286 h. The solution was evaporated to dryness and the residue was taken up in dichloromethane and washed with 1N NaOH, dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed on silica gel using 2.5% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (0.2298 g, 32%): HRFABMS: m/z 619.3169 (MH+) (Calcd. m/z 691.3163).

Provenance & Evidence