Imidazole → HCID 20735492, compound

HRID 723623Notes

Reaction equation

HRID 723623 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=1.N1C=CN=C1.[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O>[Si:30]([O:9][CH2:8][CH2:7][N:6]1[C:2]([NH2:1])=[C:3]([CH2:12][C:13]2[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:4]([CH2:10][CH3:11])=[N:5]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 9944657HCID 9944657, compound

Product 1

HCID 20735492HCID 20735492, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the pyrazole of Example 89 (3.0 g, 9.6 mmol) in dimethylformamide (20 ml) was added imidazole (850 mg, 12.5 mmol), followed by tert-butyldimethylchlorosilane (1.58 g, 10.6 mmol). The solution was stirred at room temperature for 20 hours. The reaction mixture was partitioned between diethyl ether and aqueous sodium carbonate and the aqueous phase was separated and further extracted with diethyl ether. The combined organic phases were washed with water, washed with brine, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5, by volume) to afford the title compound (4.0 g) as a colourless oil.

Workup

  1. customThe reaction mixture was partitioned between diethyl ether and aqueous sodium carbonate
  2. customthe aqueous phase was separated
  3. extractionfurther extracted with diethyl ether
  4. washThe combined organic phases were washed with water
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5, by volume)

Sources & evidence

ORD record
ord-76f53d64e3a24fe2b3b4988e4c4ab098
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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