Potassium Carbonate → HCID 11526889, compound

HRID 1715099Notes

Reaction equation

HRID 1715099 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]([F:8])([F:7])[F:6].[N:9]1([NH:15][C:16]([C:18]2[N:19]=[C:20]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=3[Cl:38])[N:21]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[C:22]=2[CH3:23])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N:9]1([NH:15][C:16]([C:18]2[N:19]=[C:20]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=3[Cl:38])[N:21]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH2:2][CH2:3][CH2:4][C:5]([F:8])([F:7])[F:6])=[CH:28][CH:29]=3)[C:22]=2[CH3:23])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27751891,1,1-Trifluoro-4-iodobutaneHCID 589650752-(2,4-Dichlorophenyl)-1-(4-hydroxyphenyl)-5-methyl-1H-imidazole-4-carboxylic acid piperidin-1-ylamide

Product 1

HCID 11526889HCID 11526889, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Iodo-4,4,4-trifluorobutane (376 mg, 1.58 mmol) was added dropwise to a suspension of 2-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)-5-methyl-1H-imidazole-4-carboxylic acid piperidin-1-ylamide, from Ex 2, Step 1 (351 mg, 0.79 mmol) and K2CO3 (218 mg, 1.58 mmol) in 50 ml acetone. The reaction mixture was refluxed overnight, cooled, filtered and concentrated. Flash chromatography (silica, hexane:EtOAc 1:2) afforded 200 mg (46%) of the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cd4623abd8a34e54869ff68276135637
Source dataset
uspto-grants-2010_09
Patent number
US07799804B2

Reaction notes

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