Water → 2-(4-(8-Bromo-2-oxo-3-(2-propylpentanoyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

HRID 476189Notes

Reaction equation

HRID 476189 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1.[C:27]([O-:30])(=O)[CH3:28].[Na+].O>C(OC(=O)C(CCC)CCC)(=O)C(CCC)CCC>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([C:27](=[O:30])[CH:28]([CH2:9][CH2:4][CH3:5])[CH2:3][CH2:2][CH3:11])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:25])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 426095694-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile2×

Product 1

HCID 498536872-(4-(8-Bromo-2-oxo-3-(2-propylpentanoyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 109236242-Propylpentanoyl 2-propylpentanoateSolvent

Procedure

A mixture of 2-(4-(8-Bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 25 mg, 0.06 mmol) and sodium acetate (5 mg, 0.06 mmol) was heated at 110-120° C. in valproic anhydride (1 ml) for four hours. Reaction mixture was cooled to RT. Water was added and extracted with ethyl acetate. Ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 12 mg (38%); 1H NMR (CDCl3, 300 MHz): δ 9.849 (s, 1H), 7.98-8.01 (d, 1H, J=9 Hz), 7.78-7.81 (d, 2H, J=8.7 Hz), 7.63-7.67 (dd, 1H, J=9, 2.1 Hz), 7.54-7.57 (d, 2H, J=8.1 Hz), 7.02-7.03 (d, 1H, J=1.8 Hz), 2.38 (m, 1H), 1.84 (s, 6H), 1.67 (m, 4H), 1.49 (m, 4H), 0.9 (m, 6H); MS: m/z 533 (M+).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. washEthyl acetate layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, 2% acetone in chloroform)

Sources & evidence

ORD record
ord-efada919a2f44e88b7442bcd28c2e171
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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