Water → HCID 22259308, compound

HRID 1610988Notes

Reaction equation

HRID 1610988 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:16])([F:15])[CH2:10][S:11](Cl)(=[O:13])=[O:12].[F:17][C:18]([F:53])([F:52])[C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]2[O:28][CH:29]=[C:30]([CH2:32][O:33][C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][CH2:43][N:44]4[CH:48]=[CH:47][N:46]=[C:45]4[CH2:49][CH2:50][NH2:51])=[CH:36][CH:35]=3)[N:31]=2)=[CH:21][CH:20]=1.O>C1COCC1>[F:8][C:9]([F:16])([F:15])[CH2:10][S:11]([NH:51][CH2:50][CH2:49][C:45]1[N:44]([CH2:43][CH2:42][CH2:41][CH2:40][C:37]2[CH:38]=[CH:39][C:34]([O:33][CH2:32][C:30]3[N:31]=[C:27](/[CH:26]=[CH:25]/[C:22]4[CH:21]=[CH:20][C:19]([C:18]([F:53])([F:52])[F:17])=[CH:24][CH:23]=4)[O:28][CH:29]=3)=[CH:35][CH:36]=2)[CH:48]=[CH:47][N:46]=1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 22259339HCID 22259339, compound

Product 1

HCID 22259308HCID 22259308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (137 μl) and 2,2,2-trifluoroethanesulfonyl chloride (65.0 l) were added to a solution of 2-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]ethylamine (250 mg) in THF (5 ml) at 0° C., and the mixture was stirred at the same temperature for 110 min. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Chromatorex) (eluent; hexane:ethyl acetate=1:2 to 1:4) and recrystallized from ethyl acetate-methanol-hexane to give the titled compound (48 mg) as colorless needle crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Chromatorex) (eluent; hexane:ethyl acetate=1:2 to 1:4)
  6. customrecrystallized from ethyl acetate-methanol-hexane

Sources & evidence

ORD record
ord-a5ce3e5f938a4727b56c33f77d49b303
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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