Imidazole → HCID 23151134, compound

HRID 1984702Notes

Reaction equation

HRID 1984702 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C:14]([O:18][C:19]([NH:21][C:22]1[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[CH:24][N:23]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(OCC)(=O)C>CN(C)C=O>[C:14]([O:18][C:19]([NH:21][C:22]1[CH:27]=[C:26]([CH2:28][O:29][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH:25]=[CH:24][N:23]=1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 231510012-(Boc-amino)-4-(hydroxymethyl)pyridine

Product 1

HCID 23151134HCID 23151134, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (2.1 g, 31 mmol) and tert-butyldimethylsilyl chloride (4.4 g, 29 mmol) were added to a solution of (2-tert-butoxycarbonylaminopyridin-4-yl)methanol (Reference compound No. 4-1, 6.2 g, 28 mmol) in N,N-dimethylformamide (120 mL) at room temperature, and the mixture was stirred for 2 hours. Ethyl acetate (300 mL) was added to the reaction mixture, then the mixture was washed with water (750 mL) and brine (200 mL), and then the mixture was dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure to give 9.0 g of the title reference compound as a colorless solid. (Yield 96%)

Workup

  1. washthe mixture was washed with water (750 mL) and brine (200 mL)
  2. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  3. customThe organic layer was evaporated under reduced pressure
  4. customto give 9.0 g of the title reference compound as a colorless solid

Sources & evidence

ORD record
ord-ea6ae4e3653f4ad3970e309a6caffcd4
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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