Hydrochloric Acid → 2-chloro-6-(hydroxymethyl)-N-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide

HRID 623633Notes

Reaction equation

HRID 623633 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12](=[O:29])[NH:13][CH:14]([C:16]2[CH:17]=[N:18][C:19]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[C:20]([CH3:22])[CH:21]=2)[CH3:15])[CH:9]=[C:8]([Cl:30])[N:7]=1)(=O)C.[OH-].[Na+].Cl>C1COCC1>[Cl:30][C:8]1[CH:9]=[C:10]([CH:11]=[C:6]([CH2:5][OH:4])[N:7]=1)[C:12]([NH:13][CH:14]([C:16]1[CH:17]=[N:18][C:19]([O:23][CH2:24][C:25]([F:27])([F:28])[F:26])=[C:20]([CH3:22])[CH:21]=1)[CH3:15])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 87426913(6-Chloro-4-((1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)pyridin-2-yl)methyl acetate

Product 1

HCID 874274592-chloro-6-(hydroxymethyl)-N-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamideYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (6-chloro-4-((1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)pyridin-2-yl)methyl acetate (95 mg, 0.21 mmol, Step-2, single enantiomer) in THF (5 mL) is added 2M aqueous sodium hydroxide solution (0.16 mL, 0.32 mmol) at room temperature, and the mixture is stirred at room temperature for 1 day. The reaction mixture is neutralized with 2M hydrochloric acid (0.16 mL, 0.32 mmol) and extracted with dichloromethane (50 mL×2). The organic layer is washed with brine, dried over sodium sulfate. The organic solvent is removed under reduced pressure to give 72 mg (84% yield) of the title compound as yellow oil.

Workup

  1. extractionextracted with dichloromethane (50 mL×2)
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe organic solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-a359dd0e81d34cb8a79c6e3ee2e6c181
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

Loading…