Ethyl Acetate → 4-(3-Chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)-amino]-(3-methyl-3h-imidazol-4-yl)-methyl]-1h-quinolin-2-one

HRID 1936318Notes

Reaction equation

HRID 1936318 reaction equation
[NH2:1][C:2]([C:27]1[CH:28]=[N:29][C:30]([Cl:33])=[CH:31][CH:32]=1)([C:21]1[N:22]([CH3:26])[CH:23]=[N:24][CH:25]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.[CH:34](=O)[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1.[OH-].N.C(OCC)(=O)C>C(O)(=O)C>[Cl:20][C:16]1[CH:15]=[C:14]([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:2]([C:27]4[CH:28]=[N:29][C:30]([Cl:33])=[CH:31][CH:32]=4)([N:1]=[CH:34][C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=4)[C:21]4[N:22]([CH3:26])[CH:23]=[N:24][CH:25]=4)[CH:4]=3)[NH:9][C:8](=[O:13])[CH:7]=2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 312444-MethoxybenzaldehydeHCID 120507296-[Amino-(6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1H-quinolin-2-oneHCID 21862953Ammonia hydroxide

Product 1

HCID 120507304-(3-Chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)-amino]-(3-methyl-3h-imidazol-4-yl)-methyl]-1h-quinolin-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the title compound of example 42 (11.89 g, 25.03 mmol) in acetic acid (75 ml) was added p-anisaldehyde (6.09 ml, 60.06 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 4 hours after which time it was cooled to 0° C. 10 ml of ammonia hydroxide was added followed by addition of ethyl acetate. After separation, the organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to yield the crude product. It was chromatographed on silica gel with MeOH-CHCl3—NH4OH (1:99:0.1 to 5:95:0.1) as eluents to afford the title compound of Example 43A as a white solid (11.58 g, 78% yield).

Workup

  1. temperaturewas cooled to 0° C
  2. customAfter separation
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customto yield the crude product
  7. customIt was chromatographed on silica gel with MeOH-CHCl3—NH4OH (1:99:0.1 to 5:95:0.1) as eluents

Sources & evidence

ORD record
ord-74bf49d893d240f8a7a8e0731d92266e
Source dataset
uspto-grants-2002_05
Patent number
US06388092B2

Reaction notes

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