1,1'-Carbonyldiimidazole → Cyclopentyl 4-(2-chloro-6-fluorophenyl)-1,4-dihydro-5-(1-imidazolylcarbonyl)-2,6-dimethylpyridine-3-carboxylate

HRID 1108295Notes

Reaction equation

HRID 1108295 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[CH:13]1([O:18][C:19]([C:21]2[CH:26]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:34])[C:25](C(O)=O)=[C:24]([CH3:38])[NH:23][C:22]=2[CH3:39])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([F:33])[C:27]=1[CH:26]1[C:25]([C:1]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[O:2])=[C:24]([CH3:38])[NH:23][C:22]([CH3:39])=[C:21]1[C:19]([O:18][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:20]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 152854344-(2-Chloro-6-fluorophenyl)-3-cyclopentyloxycarbonyl-1,4-dihydro-2,6-dimethylpyridine-5-carboxylic acidHCID 21584019Toluene ethylacetate

Product 1

HCID 15285435Cyclopentyl 4-(2-chloro-6-fluorophenyl)-1,4-dihydro-5-(1-imidazolylcarbonyl)-2,6-dimethylpyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.6 g (83 mmol) of carbonyldiimidazole are added to 33.0 g (83 mmol) of 4-(2-chloro-6-fluorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid monocyclopentyl ester in 350 ml of tetrahydrofuran and the mixture is heated under reflux for 3 hours. Monitoring by thin layer chromatography (silica gel, toluene/ethyl acetate 1:1) shows complete conversion, after which the reaction mixture is concentrated, the residue is taken up in ethyl acetate and the mixture is washed twice with water, dried over sodium sulphate and concentrated again. The target compound precipitates from ether in the form of white crystals of melting point 150° C. Yield: 29.7 g

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. concentrationafter which the reaction mixture is concentrated
  4. washthe mixture is washed twice with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated again
  7. customThe target compound precipitates from ether in the form of white crystals of melting point 150° C

Sources & evidence

ORD record
ord-0f932a94b31f418695203b226566b128
Source dataset
uspto-grants-2000_05
Patent number
US06066655

Reaction notes

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