Triethylamine → 2-(2-Acetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

HRID 1984715Notes

Reaction equation

HRID 1984715 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:13](=[S:18])[NH:14][CH:15]=[CH:16][CH:17]=2)=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:19]([NH:22][C:23]1[CH:28]=[C:27]([CH2:29]OS(C)(=O)=O)[CH:26]=[CH:25][N:24]=1)(=[O:21])[CH3:20].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O>[C:19]([NH:22][C:23]1[CH:28]=[C:27]([CH2:29][S:18][C:13]2[C:12]([C:10]([NH:9][C:4]3[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=3)=[O:11])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:26]=[CH:25][N:24]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 231510342-Acetylamino-4-methanesulfonyloxymethylpyridineHCID 23151038N-(3,5-Dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 111889642-(2-Acetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Or the compound is also synthesized in the following method. N-(3,5-Dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide (Reference compound No. 10-1, 200 mg, 0.77 mmol) and 2-acetylamino-4-methanesulfonyloxymethylpyridine (Reference compound No. 13-1, 190 mg, 0.77 mmol) were suspended in N,N-dimethylformamide (2.0 mL) under ice-cooling and under nitrogen atmosphere, then triethylamine (0.22 mL, 1.5 mmol) was added thereto, and then the mixture was stirred for 2 hours at room temperature. Ethyl acetate (40 mL) was added to the reaction mixture, and then the whole was washed with water (30 mL) and brine (20 mL). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting solid was filtered off with the solvent mixture consisting of diisopropyl ether and ethyl acetate and dried under reduced pressure at 40° C. to give 250 mg of the target compound as a pale yellow solid. (Yield 81%)

Workup

  1. customOr the compound is also synthesized in the following method
  2. temperaturecooling and under nitrogen atmosphere
  3. washthe whole was washed with water (30 mL) and brine (20 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. filtrationThe resulting solid was filtered off with the solvent mixture
  7. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-748807e7a21b424fa1335d34d34145fb
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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