Sodium Iodide → HCID 11858050, compound

HRID 1710756Notes

Reaction equation

HRID 1710756 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.Cl[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]([C:24]([N:26]([CH2:30][CH:31]3[CH2:33][CH2:32]3)[CH2:27][CH2:28][CH3:29])=[O:25])=[C:21]([CH3:23])[N:22]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH:31]1([CH2:30][N:26]([CH2:27][CH2:28][CH3:29])[C:24]([C:20]2[O:19][C:18]([C:15]3[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:3]4[CH2:4][CH2:5][CH2:6][CH:2]4[CH3:1])=[CH:17][CH:16]=3)=[N:22][C:21]=2[CH3:23])=[O:25])[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457473HCID 59457473, compound

Product 1

HCID 11858050HCID 11858050, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-methylpyrrolidine (0.24 ml, 2.46 mmol, 1.2 eq) is added to a solution of 2-[4-(3-chloropropoxy)phenyl]-N-(cyclopropylmethyl)-4-methyl-N-propyl-1,3-oxazole-5-carboxamide i44 (0.8 g, 2 mmol, 1 eq), potassium carbonate (0.55 g, 4 mmol, 2 eq) and a catalytic quantity of sodium iodide in refluxing acetonitrile (25 ml). After stirring for 20 h at reflux, the solvent is evaporated and the residue is taken up in ethyl acetate and washed two times with an aqueous solution of sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96:3.6:0.4) affords 0.31 g of N-(cyclopropylmethyl)-4-methyl-2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-N-propyl-1,3-oxazole-5-carboxamide 97.

Workup

  1. temperatureat reflux
  2. customthe solvent is evaporated
  3. washwashed two times with an aqueous solution of sodium hydrogenocarbonate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96:3.6:0.4)

Sources & evidence

ORD record
ord-daafeb98796b46d5b722e27e37060d92
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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