7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide → 5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

HRID 1453385Notes

Reaction equation

HRID 1453385 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]=1

Participants

4

Reactant 1

HCID 688469427H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

Product 1

HCID 688492915H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

10% Palladium on carbon (75 mg, 0.07 mmol) was added to a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N10-[(dimethylamino)sulfonyl]-N6-[(1,3-dimethyl-1H-pyrazol-5-yl)methyl]-3-methoxy- (60 mg, 0.09 mmol) in MeOH/CH2Cl2 (2:1, 3 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-(1,3-dimethyl-1H-pyrazol-5-yl)methyl (51 mg, 0.08 mmol, 86%) as a bright yellow solid. Mixture of atrope diasteromers: 1HNMR (300 MHz, CD3OD) δ 8.09 (s, 0.3H), 7.98 (s, 0.7H), 7.90 (d, J=8.4 Hz, 0.3H), 7.88 (d, J=8.4 Hz, 0.7H), 7.61-7.53 (m, 1H), 7.42-7.34 (m, 1H), 7.07-6.98 (m, 1.7H), 6.86 (d, J=2.6 Hz, 0.3H), 6.23 (s, 0.3H), 6.15 (s, 0.7H), 4.87-4.57 (m, 2H), 4.54-4.34 (m, 2H), 3.90 (s, 2.1H), 3.89 (s, 0.9H), 3.87 (s, 0.9H), 3.84 (s, 2.1H), 3.26-3.07 (m, 1H) 3.03 (s, 6H), 2.99-2.67 (m, 3H), 2.29 (s, 0.9H), 2.26 (s, 2.1H), 2.21-1.20 (m, 10H). LCMS: m/e 647 (M+H)+, ret time 2.01 min, column C, 2 minute gradient.

Workup

  1. customflushed with nitrogen (3×)
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cffe85b790d2432cb6f7d02f657ed2c5
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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