Imidazole → HCID 178466768, compound

HRID 2220138Notes

Reaction equation

HRID 2220138 reaction equation
[C:1]([O:5][C:6]([N:8]([C:18]1[N:23]2[N:24]=[CH:25][CH:26]=[C:22]2[C:21]([C:27]#[N:28])=[C:20]([OH:29])[C:19]=1[CH2:30][CH2:31][OH:32])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]([Si:37]([CH3:40])([CH3:39])Cl)([CH3:36])([CH3:35])[CH3:34].N1C=CN=C1.CO>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:18]1[N:23]2[N:24]=[CH:25][CH:26]=[C:22]2[C:21]([C:27]#[N:28])=[C:20]([OH:29])[C:19]=1[CH2:30][CH2:31][O:32][Si:37]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:40])[CH3:39])[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 178466767HCID 178466767, compound

Product 1

HCID 178466768HCID 178466768, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butoxy-N-[4-cyano-5-hydroxy-6-(2-hydroxyethyl)pyrazolo[1,5-a]pyridin-7-yl]-N-(4-ethoxyphenyl)carboxamide (42) (128 mg) was dissolved in dichloromethane (2.9 mL). To this solution, tert-butyldimethylchlorosilane (110 mg) and imidazole (50 mg) were added and the solution was stirred at room temperature for 3 h. To this reaction solution, methanol (2.9 mL) was added and the solution was further stirred at room temperature for 15 h. The reaction solution was diluted with ethyl acetate and washed with brine. After the organic layer was dried over sodium sulfate, the solvent was removed under reduced pressure and the residue was purified with silica-gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to obtain the title compound (43) (107.3 mg, Yield 66%).

Workup

  1. stirringthe solution was further stirred at room temperature for 15 h
  2. washwashed with brine
  3. dry with materialAfter the organic layer was dried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified with silica-gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-51533265b42442dab5ddfb8b8d9804ce
Source dataset
uspto-grants-2008_08
Patent number
US07417053B2

Reaction notes

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