Imidazole → HCID 57792032, compound

HRID 421988Notes

Reaction equation

HRID 421988 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:14][O:15][CH3:16])[C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[N:5]=[C:4]([CH2:17][OH:18])[CH:3]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:17][O:18][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[N:5]=[C:6]([N:8]([CH2:14][O:15][CH3:16])[C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57792034HCID 57792034, compound

Product 1

HCID 57792032HCID 57792032, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

18.5 g of (4-bromo-6-((methoxymethyl)(1,3-thiazol-2-yl)amino)pyridin-2-yl)-methanol was dissolved in 110 mL of dimethylformamide and 9.64 g of imidazole was added thereto. Under cooling with an ice bath, 10.2 g of tert-butyldimethylsilyl chloride was added thereto followed by stirring at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate and washed with water and brine. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 4/1) to give the title compound.

Workup

  1. temperatureUnder cooling with an ice bath
  2. washwashed with water and brine
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 4/1)

Sources & evidence

ORD record
ord-74fe00d96fc641729efd33f70ea595f7
Source dataset
uspto-grants-2012_01
Patent number
US08101621B2

Reaction notes

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