Tetrabutylammonium Fluoride → 8-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide

HRID 558990Notes

Reaction equation

HRID 558990 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][NH:13][C:14]([C:16]1[CH:47]=[CH:46][C:19]([CH2:20][NH:21][C:22]([N:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[F:34])[N:27]([CH2:35][CH2:36][O:37][Si](C(C)(C)C)(C)C)[C:26](=[O:45])[CH2:25]2)=[O:23])=[C:18]([CH3:48])[CH:17]=1)=[O:15].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][NH:13][C:14]([C:16]1[CH:47]=[CH:46][C:19]([CH2:20][NH:21][C:22]([N:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[F:34])[N:27]([CH2:35][CH2:36][OH:37])[C:26](=[O:45])[CH2:25]2)=[O:23])=[C:18]([CH3:48])[CH:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 670001684-[2-(tert-Butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide

Product 1

HCID 669995298-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-[2-(tert-butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide from Example 21F (0.34 mmol) in THF (5.0 ml) was added a solution of tetrabutylammonium fluoride in THF (1.0 M, 1.0 ml, 1.0 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 3 days. The mixture was evaporated in vacuo and the residue was taken up in CH2Cl2 and washed with ammonium chloride solution. The organic phase was dried and evaporated in vacuo and the residue was purified by flash chromatography on silica (eluant CHCl3:methanol 95:5) to give a white solid; yield 120 mg, 64%.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. customThe mixture was evaporated in vacuo
  3. washwashed with ammonium chloride solution
  4. customThe organic phase was dried
  5. customevaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica (eluant CHCl3:methanol 95:5)
  7. customto give a white solid

Sources & evidence

ORD record
ord-6da342f1447f4d7791a8d75e572dd316
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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