Water → HCID 10193632, compound

HRID 586562Notes

Reaction equation

HRID 586562 reaction equation
C([O:5][C:6]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[NH:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)=[O:7])(C)(C)C.[H-].[Na+].I[CH3:32].O>CN(C=O)C>[CH3:32][N:19]([C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:9]1[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:12][C:8]=1[C:6]([OH:5])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20826006HCID 20826006, compound

Product 1

HCID 10193632HCID 10193632, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-methyl-benzoylamino)-2-phenyl-thiazole-5-carboxylic acid t-butyl ester (50 mg) was dissolved in anhydrous DMF (5 mL). NaH (16 mg, 60% dispersion oil) was added. The mixture was stirred for 10 min., followed by adding iodomethane (25 μL). Stirring was continued for overnight and poured into water. The aqueous solution was extracted with methylene chloride, washed with water, brine and dried over MgSO4. Solvent was removed under reduced pressure. The residue was purified on silica gel using hexane:EtOAc 95:5. 9:1 and 85:5 as eluent. It yielded 25 mg of desired product.

Workup

  1. stirringStirring
  2. waitwas continued for overnight
  3. extractionThe aqueous solution was extracted with methylene chloride
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customSolvent was removed under reduced pressure
  7. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-64e5366b667f49daa7caf9d85431b62e
Source dataset
uspto-grants-2005_08
Patent number
US06936629B2

Reaction notes

Loading…