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

HRID 1453374Notes

Reaction equation

HRID 1453374 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 (80 mg, 0.08 mmol) was added to a solution of 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N6-[2-(dimethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-methyl- (35 mg, 0.06 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 for 2.5 d, filtered through a pad of celite and concentrated. The residue was purified by preparative HPLC (MeOH/H2O with an NH4OAc buffer) to yield 5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N6-[2-(dimethylamino)-2-oxoethyl]-N10-[(dimethylamino)sulfonyl]-6,7-dihydro-3-methoxy-N6-methyl- (6 mg, 0.01 mmol, 20%) as an off-white solid. 1HNMR (500 MHz, CDCl3) δ 11.11 (s, 1H), 8.09 (s. 1H), 7.74 (d, J=8.6 Hz, 1H), 7.71 (dd, J=1.2, 8.6 Hz, 1H), 7.34 (d, J=8.2 Hz, 1H), 6.96-6.90 (m, 2H), 4.85 (d, J=15.9 Hz, 1H), 4.58 (d, J=14.7 Hz, 1H), 4.04-3.84 (m, 3H), 3.89 (s, 3H), 3.51-3.45 (m, 1H), 3.35 (s, 3H), 3.40-3.20 (m, 3H), 3.09-3.01 (m, 1H), 3.04 (s, 3H), 3.03 (s, 6H), 3.00 (s, 3H), 2.64-2.58 (m, 1H), 2.10-1.19 (m, 10H). LCMS: m/e 636 (M−H)−, ret time 2.69 min, column E, 4 minute gradient.

Workup

  1. customflushed with nitrogen (3×)
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC (MeOH/H2O with an NH4OAc buffer)

Sources & evidence

ORD record
ord-84d14b284d9f40ebb81df81a478e4882
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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