Imidazole → HCID 58654364, compound

HRID 1170504Notes

Reaction equation

HRID 1170504 reaction equation
C(=O)([O-])[O-].[Cs+2].[CH3:6][O:7][N:8]([CH3:17])[C:9]([C:11]1[N:12]=[C:13](Br)[S:14][CH:15]=1)=[O:10].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>CN(C=O)C.CCOC(C)=O>[CH3:6][O:7][N:8]([CH3:17])[C:9]([C:11]1[N:12]=[C:13]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[S:14][CH:15]=1)=[O:10]

Participants

5

Reactant 2

HCID 795ImidazoleHCID 866052332-Bromo-N-methoxy-N-methylthiazole-4-carboxamide

Product 1

HCID 58654364HCID 58654364, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Cesium(II)carbonate (1.36 g, 4.18 mmol) was added to a solution of 2-bromo-thiazole-4-carboxylic acid methoxy-methyl-amide (500 mg, 1.99 mmol) and imidazole (135 mg, 1.99 mmol) in DMF (5 mL) under a nitrogen atmosphere at r.t. prior to heating at 120° C. for 40 minutes in the microwave reactor. The reaction was then cooled to r.t., diluted with EtOAc (100 mL), washed with 1M NaOH (75 mL), brine (75 mL), dried over Na2SO4, filtered and concentrated to a white solid. Purification was achieved using column chromatography (CH2Cl2 to 9:1 CH2Cl2/MeOH) to afford 435 mg (92%) of 2-imidazol-1-yl-thiazole-4-carboxylic acid methoxy-methyl-amide as a white solid. [M+H]+ 239.02.

Workup

  1. temperatureThe reaction was then cooled to r.t.
  2. washwashed with 1M NaOH (75 mL), brine (75 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid
  6. customPurification

Sources & evidence

ORD record
ord-8b2aacf67d004a399b8931c80b874527
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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