5-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride → Tak-259

HRID 447887Notes

Reaction equation

HRID 447887 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:22]([NH2:24])=[O:23])[C:6](=[NH:21])[N:7]([CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=1>[OH-].[Na+]>[Cl:2][C:3]1[CH:4]=[C:5]([C:22]([NH2:24])=[O:23])[C:6](=[NH:21])[N:7]([CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=1

Participants

3

Reactant 1

HCID 669700865-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride

Product 1

HCID 44247584Tak-259Yield 84.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

5-Chloro-1-[5-chloro-2-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride obtained in Example 1 (0.30 g) was dissolved in 1N aqueous sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The precipitated crystals were collected by filtration to give the title compound (0.23 g).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-e66b35ffb4e34dd4aa5e90957621681b
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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