Imidazole → HCID 59812765, compound

HRID 558310Notes

Reaction equation

HRID 558310 reaction equation
Cl[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([O:18][C:19]2[C:20]([CH3:28])=[N:21][N:22]([CH2:25][CH2:26][OH:27])[C:23]=2[CH3:24])[CH:17]=1)[C:13]#[N:14].N1C=CN=C1.O>CN(C)C=O>[Si:2]([O:27][CH2:26][CH2:25][N:22]1[C:23]([CH3:24])=[C:19]([O:18][C:16]2[CH:15]=[C:12]([CH:11]=[C:10]([Cl:9])[CH:17]=2)[C:13]#[N:14])[C:20]([CH3:28])=[N:21]1)([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 21949851HCID 21949851, compound

Product 1

HCID 59812765HCID 59812765, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloro-t-butyldimethylsilane (2.78 g, 18.5 mmol) was added in one portion to a stirred solution of the pyrazole of Example 114 (4.89 g, 16.8 mmol) and imidazole (1.48 g, 21.8 mmol) in N,N-dimethylformamide (30 ml) at room temperature under nitrogen. The reaction was stirred for 3 days and water (200 ml) was added. The aqueous phase was extracted with diethyl ether (3×200 ml) and the combined organic phases were washed with water (2×50 ml) and brine (2×50 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane to provide the title compound (5.60 g) as a yellow oil.

Workup

  1. extractionThe aqueous phase was extracted with diethyl ether (3×200 ml)
  2. washthe combined organic phases were washed with water (2×50 ml) and brine (2×50 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-b7203e68e13243d48e838f69518d4a4d
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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