Water → HCID 22259355, compound

HRID 1610955Notes

Reaction equation

HRID 1610955 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=[CH:4]1)=[O:2].[F:13][C:14]([F:49])([F:48])[C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[O:24][CH:25]=[C:26]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][CH2:39][N:40]4[CH:44]=[CH:43][N:42]=[C:41]4[CH2:45][CH2:46][OH:47])=[CH:32][CH:31]=3)[N:27]=2)=[CH:17][CH:16]=1.CN.O>C1COCC1>[CH3:4][NH:3][C:1](=[O:2])[O:47][CH2:46][CH2:45][C:41]1[N:40]([CH2:39][CH2:38][CH2:37][CH2:36][C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:28][C:26]3[N:27]=[C:23](/[CH:22]=[CH:21]/[C:18]4[CH:19]=[CH:20][C:15]([C:14]([F:48])([F:13])[F:49])=[CH:16][CH:17]=4)[O:24][CH:25]=3)=[CH:31][CH:32]=2)[CH:44]=[CH:43][N:42]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22259324HCID 22259324, compound

Product 1

HCID 22259355HCID 22259355, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,1′-Carbonyldiimidazole (143 mg) was 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]-1-ethanol (300 mg) in THF (3 ml) at 0° C., and the mixture was stirred at the same temperature for 3 hr. A solution (2.0 M; 1.47 ml) of methylamine in THF was added to the reaction mixture at 0° C., and the mixture was stirred at the same temperature for 3 hr and at room temperature for 30 min. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and recrystallized from diethyl ether-acetone-hexane to give the titled compound (310 mg) as a colorless crystal powder.

Workup

  1. stirringthe mixture was stirred at the same temperature for 3 hr and at room temperature for 30 min
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customrecrystallized from diethyl ether-acetone-hexane

Sources & evidence

ORD record
ord-a896d211b6f14926b452755110e110c1
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

Loading…