2,2,2-Trifluoroethanol → HCID 89435477, compound

HRID 1774684Notes

Reaction equation

HRID 1774684 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].C1(OC(=O)O[CH2:18][N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][N:37]([C:40]5[C:48]6[CH:47]=[CH:46][S:45][C:44]=6[CH:43]=[CH:42][CH:41]=5)[CH2:36][CH2:35]4)[CH:27]=3)[CH2:22][CH2:21][C:20]2=[O:49])C=CC=CC=1>C1COCC1>[S:45]1[CH:46]=[CH:47][C:48]2[C:40]([N:37]3[CH2:36][CH2:35][N:34]([CH2:33][CH2:32][CH2:31][CH2:30][O:29][C:26]4[CH:27]=[C:28]5[C:23]([CH2:22][CH2:21][C:20](=[O:49])[N:19]5[CH2:18][O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[CH:24][CH:25]=4)[CH2:39][CH2:38]3)=[CH:41][CH:42]=[CH:43][C:44]1=2

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 86273004HCID 86273004, compound

Product 1

HCID 89435477HCID 89435477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,2,2-Trifluoroethanol (0.10 ml) was dissolved in anhydrous THF (3 ml) under a nitrogen atmosphere and sodium hydride (about 55% oil) (60 mg) was added under ice-cooling. The reaction mixture was stirred at room temperature for 30 min under a nitrogen atmosphere. The obtained solution was ice-cooled again and, under a nitrogen atmosphere, a solution (3 ml) of carbonic acid 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethyl ester phenyl ester (0.25 g) obtained in Example 5 in anhydrous THF was added using a cannula. The reaction mixture was stirred at room temperature for 18 hr under a nitrogen atmosphere. To the reaction mixture was added ice water to discontinue the reaction, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated by filtration. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (90 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooled again and, under a nitrogen atmosphere
  3. stirringThe reaction mixture was stirred at room temperature for 18 hr under a nitrogen atmosphere
  4. customthe reaction
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated by filtration
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ef6d31ce9fd54199a5c14b295d34b68d
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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