Benzoyl bromide → 2-(4-(3-Benzoyl-8-chloro-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

HRID 476197Notes

Reaction equation

HRID 476197 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[NH:14][C:15](=[O:28])[N:16]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])=[CH:19][CH:18]=4)[C:7]=3[C:6]=2[CH:5]=1.[C:29](Br)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[C:29]([N:14]1[C:8]2[CH:9]=[N:10][C:11]3[CH:12]=[CH:13][C:4]([Cl:3])=[CH:5][C:6]=3[C:7]=2[N:16]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:27])[C:24]#[N:25])=[CH:19][CH:18]=2)[C:15]1=[O:28])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 12056Benzoyl bromideHCID 24758Sodium hydrideHCID 668963372-(4-(8-chloro-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile2×

Product 1

HCID 498537952-(4-(3-Benzoyl-8-chloro-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (22 mg, 0.557 mmol) was added to dry DMF (5 mL) in a nitrogen atmosphere. The reaction flask was cooled in an ice-bath to 0° C., and 2-(4-(8-chloro-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 2, 100 mg, 0.27 mmol) was added. After 15 minutes benzoyl bromide (61 mg, 0.33 mmol) was added, and the reaction mixture was heated at 50° C. for 24 hours. The reaction mixture was concentrated in vacuum. The crude product was purified by column chromatography (silica gel, 2.5% acetone in chloroform) to obtain the title compound. Yield: 30 mg (23%); 1H NMR (DMSO-d6, 300 MHz): δ 9.372 (s, 1H), 8.048-8.078 (d, 1H, J=9 Hz), 7.905-7.929 (d, 2H, J=7.2 Hz), 7.810-7.839 (d, 2H, J=8.7 Hz), 7.730-7.759 (d, 2H, J=8.7 Hz), 7.611-7.666 (m, 2H), 7.449-7.523 (m, 2H), 6.698-6.705 (d, 1H, J=2.1 Hz), 1.752 (s, 6H); MS: m/z 467 (M+).

Workup

  1. temperaturethe reaction mixture was heated at 50° C. for 24 hours
  2. concentrationThe reaction mixture was concentrated in vacuum
  3. customThe crude product was purified by column chromatography (silica gel, 2.5% acetone in chloroform)

Sources & evidence

ORD record
ord-9a8f2b4cff024003a1de600a9bfaa5e2
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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