Triethylamine → 2,3-Dimethyl-N-(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)-benzamide

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Reaction Steps

Preparation of example 98 from the title compound of Example 7 (hydrochloride) (42 mg, 0.134 mmol), 2,3-dimethyl-benzoic acid (24 mg, 0.161 mmol), triethylamine (0.056 mL, 0.402 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (61 mg, 0.161 mmol) in CH2Cl2 (0.4 mL) and N,N-dimethylformamide (0.4 mL) was carried out analogously to Example 11. The mixture was stirred as a thick slurry and additional 2,3-dimethyl-benzoic acid (12 mg, 0.08 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (30 mg, 0.08 mmol) were added after 48 hours to drive the reaction to completion. The mixture was filtered to collect the solids which were then washed with methanol. After drying the solids under high vacuum, the title compound (32 mg, 0.078 mmol) was obtained as a yellow powder in 58% yield.

Provenance & Evidence