Potassium Carbonate → ethyl 4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-[(2-phenyl-1H-imidazol-1-yl)(4-phenyl-2-thiazolyl)methyl]-3-quinolinecarboxylate

HRID 1830816Notes

Reaction equation

HRID 1830816 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18](Cl)[C:19]4[S:20][CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[N:23]=4)[CH:16]=3)[NH:11][C:10](=[O:31])[C:9]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:5]=[CH:6][CH:7]=1.[C:37]1([C:43]2[NH:44][CH:45]=[CH:46][N:47]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([N:44]4[CH:45]=[CH:46][N:47]=[C:43]4[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:19]4[S:20][CH:21]=[C:22]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:23]=4)[CH:16]=3)[NH:11][C:10](=[O:31])[C:9]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 695912-PhenylimidazoleHCID 22048490Ethyl 4-(3-chlorophenyl)-6-[chloro(4-phenyl-2-thiazolyl)methyl]-1,2-dihydro-2-oxo-3-quinolinecarboxylate

Product 1

HCID 22048487ethyl 4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-[(2-phenyl-1H-imidazol-1-yl)(4-phenyl-2-thiazolyl)methyl]-3-quinolinecarboxylateYield 5.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of intermediate (20) (0.0245 mol), 2-phenyl-1H-imidazole (0.0368 mol) and K2CO3 (0.0735 mol) in acetonitrile (150n) was stirred at 60° C. The solvent was evaporated till dryness. The residue was taken up in DCM and water. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.8 g (5.1%) of ethyl 4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-[(2-phenyl-1H-imidazol-1-yl)(4-phenyl-2-thiazolyl)methyl]-3-quinolinecarboxylate.

Workup

  1. customThe solvent was evaporated till dryness
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-85fae8dde66846bdb1c3fb598379479b
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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