Sodium Iodide → HCID 11857968, compound

HRID 1710753Notes

Reaction equation

HRID 1710753 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[N:16]=2)=[CH:8][CH:7]=1.[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[N:16]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457492HCID 59457492, compound

Product 1

HCID 11857968HCID 11857968, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-({2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}carbonyl)morpholine i35 (0.26 g, 0.75 mmol, 1 eq) is reacted with 2-methylpyrrolidine (0.11 ml, 1.13 mmol, 1.5 eq) in the presence of potassium carbonate (0.2 g, 1.5 mmol, 2 eq) and a catalytic amount of sodium iodide in refluxing acetonitrile (15 ml) overnight. The solvent is then evaporated, and the residue 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 0.11 g of 4-[(2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)carbonyl]morpholine 90.

Workup

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

Sources & evidence

ORD record
ord-e8eb7ed49d9d407c85fd14b48fb4aecd
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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