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

HRID 1394894Notes

Reaction equation

HRID 1394894 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 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (70 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-(2-hydroxyethyl)-3-methoxy-N6-methyl- (64 mg, 0.11 mmol) in MeOH (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-N6-(2-hydroxyethyl)-3-methoxy-N6-methyl-(50 mg, 0.08 mmol, 78%) as a yellow solid. Mixture of atrope diasteromers:

Workup

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

Sources & evidence

ORD record
ord-31163c0607e44434b0babd5b1c9f6394
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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