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

HRID 1394893Notes

Reaction equation

HRID 1394893 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]=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 23938PalladiumCatalyst2×HCID 887MethanolSolvent

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-N10-[(dimethylamino)sulfonyl]-N6,N6-bis(2-hydroxyethyl)-3-methoxy- (47 mg, 0.08 mmol) in MeOH (3 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. Additional 10% palladium on carbon (30 mg, 0.03 mmol) was added and the reaction mixture was once again 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-N11-[(dimethylamino)sulfonyl]-6,7-dihydro-N6,N6-bis(2-hydroxyethyl)-3-methoxy- (39 mg, 0.06 mmol, 83%) as a yellow solid. Mixture of atrope diasteromers: 1HNMR (300 MHz, CD3OD) δ 8.13-7.93 (m, 1H), 7.88-7.79 (m, 1H), 7.66-7.58 (m, 1H), 7.40-7.31 (m, 1H), 7.06-6.88 (m, 2H), 4.56-4.34 (m, 2H), 3.94-3.86 (m, 3H), 3.85-3.64 (m, 8H), 3.48-3.37 (m, 1H), 3.03-2.82 (m, 2H), 2.99 (s, 6H), 2.77-2.63 (m, 1H), 2.19-1.17 (m, 10H). LCMS: m/e 625 (M−H)−, ret time 2.44 min, column A, 4 minute gradient.

Workup

  1. customflushed with nitrogen (3×)
  2. customflushed with nitrogen (3×)
  3. stirringThe reaction was stirred under a balloon of hydrogen overnight
  4. filtrationfiltered through a pad of celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-943621f46c5f41b88aa9d446afc816d9
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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