p-Toluenesulfonic acid → HCID 14182525, compound

HRID 1252633Notes

Reaction equation

HRID 1252633 reaction equation
COC1C=CC(C[N:10]2[CH:15]=[C:14]([O:16]CC3C=CC=CC=3)[C:13](=[O:24])[CH:12]=[C:11]2[C:25]([NH:27][CH2:28][CH2:29][NH:30]CC2C=CC=CC=2)=[O:26])=CC=1.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1.[H][H]>CO.[Pd]>[C:38]1([CH3:48])[CH:39]=[CH:40][C:41]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:42][CH:43]=1.[NH2:30][CH2:29][CH2:28][NH:27][C:25]([C:11]1[NH:10][CH:15]=[C:14]([OH:16])[C:13](=[O:24])[CH:12]=1)=[O:26]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14182523HCID 14182523, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14182525HCID 14182525, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1,4-Dihydro-1-[(4-methoxyphenyl)methyl]-4-oxo-5-(phenylmethoxy)-N-[2-[(phenylmethyl)amino]ethyl]-2-pyridinecarboxamide (9.95 g) and 7.7 g of p-toluenesulfonic acid in 100 ml of methanol were treated with 3 g of palladium on charcoal (10%) and hydrogen was bubbled through the reaction mixture at 45°-50° C. over six hours. A stream of argon was then bubbled through the reaction mixture for 10 minutes. Filtration and evaporation of the filtrate yielded beige crystals of the title compound which were washed first with 20 ml of cold methanol and then 50 ml of ether. Yield: 10.5 g, melting point 271° C.

Workup

  1. customwas bubbled through the reaction mixture at 45°-50° C. over six hours
  2. customA stream of argon was then bubbled through the reaction mixture for 10 minutes
  3. filtrationFiltration and evaporation of the filtrate

Sources & evidence

ORD record
ord-bffe38bb03a54edd95270e7d3fb81376
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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