Sodium Iodide → HCID 23001175, compound

HRID 397975Notes

Reaction equation

HRID 397975 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][C:6]1[NH:11][C:10]([CH3:12])=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:7]=1[C:24](=[O:41])[NH:25][CH2:26][CH2:27][CH:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[I-].[Na+].[N-:44]=[N+]=[N-].[Na+].CN(C=O)C>CC(O)C.C(OCC)(=O)C>[NH2:44][CH2:2][CH2:3][O:4][CH2:5][C:6]1[NH:11][C:10]([CH3:12])=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:7]=1[C:24](=[O:41])[NH:25][CH2:26][CH2:27][CH:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 33557Sodium AzideHCID 23001155HCID 23001155, compound

Product 1

HCID 23001175HCID 23001175, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.12 g (0.20 mmol) of methyl 6-(2-chloroethoxy)methyl-4-(3-chlorophenyl)-5-(3,3-diphenylpropylcarbamoyl)-2-methyl-1,4-dihydropyridine-3-carboxylate and 0.030 g (0.20 mmol) of sodium iodide were dissolved in 2 ml of 2-propanol, and the obtained solution was stirred at 70° C. for 24 hours. The solvent was evaporated under reduced pressure. Dichloromethane was added to the residue, and sodium iodide thus precipitated was separated by the filtration. The filtrate was treated under reduced pressure, and 15 mg (0.23 mmol) of sodium azide and 2 ml of DMF were added thereto. The reaction mixture was stirred at 50° C. for 16 hours. Ethyl acetate was added thereto. After washing with water and saturated aqueous sodium chloride solution, the organic layer was concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=7/3) to obtain the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionDichloromethane was added to the residue, and sodium iodide
  3. customthus precipitated
  4. customwas separated by the filtration
  5. additionwere added
  6. stirringThe reaction mixture was stirred at 50° C. for 16 hours
  7. washAfter washing with water and saturated aqueous sodium chloride solution
  8. concentrationthe organic layer was concentrated under reduced pressure
  9. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-b831095505f8434fbd62cba8fc90ef69
Source dataset
uspto-grants-2003_08
Patent number
US06610717B2

Reaction notes

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