Triethylamine → 2-(Quinolin-4-ylmethylthio)-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide

HRID 599363Notes

Reaction equation

HRID 599363 reaction equation
C(N(CC)CC)C.[SH:8][C:9]1[C:14]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1.Cl[CH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>CN(C)C=O>[N:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31]([CH2:30][S:8][C:9]2[C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:26])([F:27])[F:28])=[CH:20][CH:19]=3)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 123557014-(Chloromethyl)quinolineHCID 1785222352-mercapto-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide

Product 1

HCID 118470442-(Quinolin-4-ylmethylthio)-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (66 μL, 0.47 mmol) was added to a solution of 2-mercapto-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide (Reference Compound No. 8-3, 52 mg, 0.17 mmol) and 4-(chloromethyl)quinoline (Reference Compound No. 5-1, 28 mg, 0.16 mmol) in anhydrous N,N-dimethylformamide (11.0 mL) at room temperature, and the mixture was stirred for 18 hours. Ethyl acetate (50 mL) was added thereto, then the whole was washed with saturated aqueous sodium hydrogencarbonate solution (5 mL) and brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography to give 40 mg of the title compound as a white amorphous (Yield: 52%).

Workup

  1. washthe whole was washed with saturated aqueous sodium hydrogencarbonate solution (5 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ce95029d13354666ae5c0ec456e1fa88
Source dataset
uspto-grants-2011_03
Patent number
US07897774B2

Reaction notes

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