7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide → 5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide
Reaction equation
[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([NH2:21])=[O:20])=[CH:17][C:18]=4[N:9]3[CH2:8][C:7]([C:22]([NH2:24])=[O:23])=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>[Pd].CO.C(Cl)Cl>[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([NH2:21])=[O:20])=[CH:17][C:18]=4[N:9]3[CH:8]=[C:7]([C:22]([NH2:24])=[O:23])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
10% Palladium on carbon (77 mg, 0.07 mnol) was added to a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-(2-methoxyethyl)-N6-methyl- (65 mg, 0.11 mmol) in MeOH/CH2Cl2 (1:1, 4 mL) and the reaction mixture was vacuum flushed with nitrogen (3×) and then with hydrogen (3×). The reaction was stirred under a balloon of hydrogen overnight, filtered through a pad of celite and concentrated to yield 5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N10-[(dimethylamino)sulfonyl]-6,7-dihydro-3-methoxy-N6-(2-methoxyethyl)-N6-methyl- (60 mg, 0.10 mmol, 92%) as a light yellow solid. Mixture of atrope diastereomers. 1HNMR (300 MHz, CD3OD) δ 8.10-7.92 (m, 1H), 7.91-7.83 (m, 1H), 7.62-7.51 (m, 1H), 7.42-7.33 (m, 1H), 7.10-6.84 (m, 2H), 4.67-4.44 (m, 1H), 3.93-3.86 (m, 3H), 3.84-3.21 (m, 1H), 3.06-2.86 (m, 8H), 2.83-2.64 (m, 2H), 2.18-1.19 (m, 10H). LCMS: m/e 611 (M+H)+, ret time 2.12 min, column C, 2 minute gradient.
Workup
- customflushed with nitrogen (3×)
- filtrationfiltered through a pad of celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2371824742464c8fa53263a8cdde1b83
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473688B2
Reaction notes
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