[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@@H:16]4[CH2:25][CH2:24][C:19]5(OCC[O:20]5)[CH2:18][C@H:17]4[CH3:26])=[N:13][CH:12]=[C:11]([C:27]#[N:28])[C:7]=3[NH:8][C:9]=2[CH:10]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CC(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@@H:16]4[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][C@H:17]4[CH3:26])=[N:13][CH:12]=[C:11]([C:27]#[N:28])[C:7]=3[NH:8][C:9]=2[CH:10]=1To a stirred solution of 7-chloro-1-{[(7R,8R)-7-methyl-1,4-dioxaspiro[4.5]dec-8-yl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (147 mg, 0.37 mmol) in acetone (15 mL) was added pTsOH.H2O (176 mg, 0.93 mmol). The mixture was left to stir overnight, diluted with EtOAc, and washed with aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate), and concentrated to afford the title compound. LRMS (APCI) calc'd for (C19H17ClN4O) [M+H]+, 353.1. found 353.0.
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