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

HRID 1453388Notes

Reaction equation

HRID 1453388 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 (60 mg, 0.06 mmol) was added to a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-methyl-N6-[2-(4-morpholinyl)-2-oxoethyl]- (59 mg, 0.09 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. The reaction mixture was once again vacuum flushed with nitrogen (3×) and then with hydrogen (3×) and stirred under a balloon of hydrogen overnight. The solution was 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-methyl-N6-[2-(4-morpholinyl)-2-oxoethyl]- (31 mg, 0.05 mmol, 53%) as a yellow solid. Mixture of atrope diastereomers: 1HNMR (500 MHz, CDCl3) δ 10.85 (br s, 1H), 8.07 (s, 1H), 7.85 (d, J=8.5 Hz, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.34 (d, J=8.2 Hz, 1H), 6.93 (d, J=8.2 Hz, 1H), 6.91 (s, 1H), 4.75-4.33 (m, 2H), 3.88 (s, 3H), 3.94-2.44 (m, 13H), 3.31 (s, 3H), 3.02 (s, 6H), 2.95-2.84 (m, 1H), 2.19-1.17 (m, 10H). LCMS: m/e 678 (M−H)−, ret time 2.77 min, column A, 4 minute gradient.

Workup

  1. customflushed with nitrogen (3×)
  2. customflushed with nitrogen (3×)
  3. stirringwith hydrogen (3×) and stirred under a balloon of hydrogen overnight
  4. filtrationThe solution was filtered through a pad of celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c709a66da4047ce806e7bbb730ed0c8
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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