Sodium Iodide → HCID 86590784, compound

HRID 1727911Notes

Reaction equation

HRID 1727911 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:12]([C:21](=[O:38])[NH:22][CH2:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:11]([CH2:39][O:40][CH2:41][CH2:42]Cl)[NH:10][C:9]=1[CH3:44])=[O:7])#[N:2].[I-].[Na+].[N-:47]=[N+:48]=[N-:49].[Na+].C(OCC)(=O)C>CC(O)C.CN(C=O)C>[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:12]([C:21](=[O:38])[NH:22][CH2:23][CH2:24][CH:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:11]([CH2:39][O:40][CH2:41][CH2:42][N:47]=[N+:48]=[N-:49])[NH:10][C:9]=1[CH3:44])=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 69940917HCID 69940917, compound

Product 1

HCID 86590784HCID 86590784, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

270 mg (0.430 mmol) of 6-(2-chloroethoxy) methyl-4-(3-chlorophenyl)-5-(3,3-diphenylpropylcarbamoyl)-2-methyl-1,4-dihydropyridine-3-carboxylic acid (2-cyanoethyl) ester was dissolved in 3 ml of 2-propanol. 600 mg (0.400 mmol) of sodium iodide was added thereto and stirred at 60° C. for 20 hours. After the solvent was evaporated under reduced pressure, sodium iodide separated by adding dichloromethane was taken by filtration. The filtrate was concentrated under reduced pressure and stirred together with 33.0 mg (0.490 mmol) of sodium azide at 50° C. for 6 hours in 2 ml of DMF. After adding ethyl acetate, the reaction mixture was washed with water and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. customAfter the solvent was evaporated under reduced pressure, sodium iodide
  2. customseparated
  3. additionby adding dichloromethane
  4. filtrationwas taken by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe reaction mixture was washed with water and saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4178ff102ce747ceb04f89cb96b3e768
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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