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

HRID 987008Notes

Reaction equation

HRID 987008 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[CH:21]1[C:26](C(O)=O)=[C:25]([CH3:30])[NH:24][C:23]([CH3:31])=[C:22]1[C:32]([O:34][CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:33].C1(C)C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[CH:21]1[C:26]([C:1]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[O:2])=[C:25]([CH3:30])[NH:24][C:23]([CH3:31])=[C:22]1[C:32]([O:34][CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:33]

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)-3-cyclopentyloxycarbonyl-1.4-dihydro-2,6-dimethylpyridine-5-carboxylic acid in 350 ml of tetrahydrofuran and the mixture is heated to reflux for 3 h. Thin-layer chromatographic checking (silica gel, toluene/ethyl acetate 1:1) shows complete reaction, after which the reaction mixture is concentrated, the residue is taken up in ethyl acetate, and the solution 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 m.p. 150° C.

Workup

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

Sources & evidence

ORD record
ord-b3d851f4dd9344baa677055af27932aa
Source dataset
uspto-grants-2003_10
Patent number
US06630494B2

Reaction notes

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