Imidazole → HCID 21055102, compound

HRID 2114673Notes

Reaction equation

HRID 2114673 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:24]=[C:25]([Cl:27])[CH:26]=1)[O:13][C:14]1[C:15]([CH3:23])=[N:16][N:17]([CH2:20][CH2:21][OH:22])[C:18]=1[CH3:19].N1C=CN=C1.O>CN(C)C=O>[Si:2]([O:22][CH2:21][CH2:20][N:17]1[C:18]([CH3:19])=[C:14]([O:13][C:12]2[CH:24]=[C:25]([Cl:27])[CH:26]=[C:10]([Cl:9])[CH:11]=2)[C:15]([CH3:23])=[N:16]1)([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 9944171HCID 9944171, compound

Product 1

HCID 21055102HCID 21055102, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloro-t-butyldimethylsilane (1.93 g, 12.8 mmol) was added in one portion to a stirred solution of the pyrazole of Example 1 (3.50 g, 11.6 mmol) and imidazole (1.03 g, 15.1 mmol) in N,N-dimethylformamide (23 ml) at room temperature under nitrogen. The reaction was stirred for 2 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 pentane:ethyl acetate (80:20, by volume) to provide the title compound (4.82 g) as a colourless 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 pentane:ethyl acetate (80:20, by volume)

Sources & evidence

ORD record
ord-7446495e97f34fbdbb3427702acd2fb9
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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