Dimethylformamide → HCID 59351688, compound

HRID 1889410Notes

Reaction equation

HRID 1889410 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:20]([O:22]C)=O)[CH:4]=1)[CH3:2].CN(C)C=O.[H-].[Na+].Br[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:40]([C:45]#[N:46])=[CH:41][CH:42]=[CH:43][CH:44]=2)=[CH:35][CH:34]=1>C(OCC)(=O)C>[CH2:1]([C:3]1[S:7][C:6]2[N:8]([CH2:32][C:33]3[CH:34]=[CH:35][C:36]([C:39]4[C:40]([C:45]#[N:46])=[CH:41][CH:42]=[CH:43][CH:44]=4)=[CH:37][CH:38]=3)[C:9](=[O:19])[C:10]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[C:20]([OH:22])[C:5]=2[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 59351472HCID 59351472, compound

Product 1

HCID 59351688HCID 59351688, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 5-ethyl-2-[(4-phenylbutanoyl)amino]thiophene-3-carboxylate (15 g) and N,N-dimethylformamide (150 mL) was added 60% sodium hydride (2.17 g), and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added 4′-(bromomethyl)biphenyl-2-carbonitrile (14.8 g), and the mixture was further stirred for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% potassium hydrogensulfate and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. After purification by silica gel column chromatography, the obtained residue was dissolved in tetrahydrofuran (200 mL), potassium tert-butoxide (5.3 g) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was extracted with saturated aqueous ammonium chloride solution and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless oil (4.89 g, 22%).

Workup

  1. stirringthe mixture was further stirred for 3 hr
  2. washwashed with 5% potassium hydrogensulfate
  3. dry with materialsaturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customAfter purification by silica gel column chromatography
  6. dissolutionthe obtained residue was dissolved in tetrahydrofuran (200 mL)
  7. additionpotassium tert-butoxide (5.3 g) was added
  8. stirringthe mixture was stirred at room temperature for 16 hr
  9. extractionThe reaction mixture was extracted with saturated aqueous ammonium chloride solution and ethyl acetate
  10. washThe obtained ethyl acetate layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-54b2d14dbb9c4fa9886566dcdf6b797b
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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