Water → 4-Morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 2263367Notes

Reaction equation

HRID 2263367 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:21]Br)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.O>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:21][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 179517684-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

Product 1

HCID 595946784-Morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 69.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 500 mg of 4-bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester in 5 mL of acetonitrile was added 190 mg of potassium carbonate and 110.5 mg of morpholine. The resulting mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 50/50) followed by washing of the collected solid with diisopropyl ether to give 355 mg of 4-morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 50/50)
  6. washby washing of the collected solid with diisopropyl ether

Sources & evidence

ORD record
ord-5067e6cf5c034caea3319a75abeb5214
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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