[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:27]#[N:28])=[CH:12][N:13]=[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])[C:5]=3[C:4]=2[CH:3]=1.Cl>CC(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:27]#[N:28])=[CH:12][N:13]=[C:14]([NH:15][C@@H:16]4[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][C@H:17]4[CH3:26])[C:5]=3[C:4]=2[CH:3]=1To a stirred solution of 8-fluoro-1-{[(7R,8R)-7-methyl-1,4-dioxaspiro[4.5]dec-8-yl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (8.5 g, 22.3 mmol) in acetone (100 mL) was added HCl (1 M, 100 mL, 100 mmol). The mixture was heated to 50° C. for 1 h, diluted with EtOAc, and washed with 1 N NaOH. The organic layer was dried (sodium sulfate), and concentrated to afford the title compound. LRMS (APCI) calc'd for (C19H17FN4O) [M+H]+, 337.1. found 337.0.
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