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>[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 (50 mg, 0.05 mmol) was added to a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N6-[2-(diethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-methyl- (51 mg, 0.08 mmol) in MeOH (2 mL) and the reaction mixture was vacuum flushed with nitrogen (3×) and then with hydrogen (3×). The reaction mixture 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-N6-[2-(diethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-6,7-dihydro-3-methoxy-N6-methyl- (44 mg, 0.07 mmol, 86%) as an off-white solid. Partial 1HNMR (300 MHz, CDCl3) δ 11.3 (s, 1H), 8.04 (s, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 6.94-6.86 (m, 2H), 4.80-4.71 (m, 1H), 4.60-4.52 (m, 1), 3.86 (s, 3H), 3.33 (s, 3H), 3.01 (s, 6H). LCMS: m/e 664 (M−H)−, ret time 3.12 min, column A, 4 minute gradient.
Workup
- customflushed with nitrogen (3×)
- filtrationfiltered through a pad of celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8230aacf446b43f49f7cdc244258975f
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473688B2
Reaction notes
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