Acetic Acid → Ethyl 1,4-dihydro-2,6-diisopropyl-4-(4-fluorophenyl)-5-phenyl-pyridine-3-carboxylate

HRID 1609564Notes

Reaction equation

HRID 1609564 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14](=O)[CH:15]([CH3:17])[CH3:16])=[CH:8][CH:7]=1.[NH2:25][C:26]([CH:33]([CH3:35])[CH3:34])=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C(O)CO>[CH:33]([C:26]1[NH:25][C:14]([CH:15]([CH3:17])[CH3:16])=[C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]([C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)[C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 544349341-(4-Fluorophenyl)-4-methyl-2-phenyl-penten-3-oneHCID 59557418Ethyl 3-amino-4-methyl-pent-2-enoate

Product 1

HCID 20081859Ethyl 1,4-dihydro-2,6-diisopropyl-4-(4-fluorophenyl)-5-phenyl-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

2.86 ml (50 mmol) of glacial acetic acid are added to 13.45 g (50 mmol) of the compound from Example 97 and 17.4 g (100 ml) of ethyl 3-amino-4-methyl-pent-2-enoate in 80 ml of ethylene glycol and the mixture is heated to reflux overnight. After cooling to room temperature, it is concentrated vacuo and the residue is dissolved in dichloromethane and extracted several times using water. The organic phase is dried over magnesium sulphate and concentrated in vacuo, and the residue is taken up in ethyl acetate. After extracting using 10% strength hydrochloric acid, water and saturated sodium hydrogen carbonate solution, the organic phase is dried again and concentrated, and the residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether)).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux overnight
  3. concentrationit is concentrated vacuo
  4. dissolutionthe residue is dissolved in dichloromethane
  5. extractionextracted several times
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. extractionAfter extracting
  9. customthe organic phase is dried again
  10. concentrationconcentrated
  11. customthe residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether))

Sources & evidence

ORD record
ord-eb77d059aecd40ba92e161ce3b525c19
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

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