[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C[Al](C)C.[Cl:11][C:12]1[CH:32]=[CH:31][C:15]2[C:16](=[O:30])[C:17]3[C:24]([C:25](OCC)=[O:26])=[N:23][NH:22][C:18]=3[C:19](=[O:21])[NH:20][C:14]=2[CH:13]=1>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:32]=[CH:31][C:15]2[C:16](=[O:30])[C:17]3[C:24]([C:25]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:26])=[N:23][NH:22][C:18]=3[C:19](=[O:21])[NH:20][C:14]=2[CH:13]=1Morpholine (268 μL, 3.06 mmol) was added to a solution of trimethylaluminum in toluene (1.56 mL, 3.13 mmol) and the solution was stirred for 20 minutes. A portion (365 μL) of the resulting solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (100 mg, 0.313 mmol) in toluene (0.760 mL). The resulting solution was stirred for 4 hours at room temperature and then quenched with aqueous hydrochloric acid (1.88 mL, 1N) and water (50 mL). The aqueous layer was extracted with chloroform (7×50 mL) and ethyl acetate (3×50 mL). The combined organic layers were concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20) to give the title compound (89.9 mg, 80% yield, m.p. 347° C.).
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