Sodium Hydroxide → HCID 23093762, compound

HRID 493241Notes

Reaction equation

HRID 493241 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([NH:11][C:12]([C:14]2[C:15]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]([O:30]CC)=[O:29])[CH:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])[CH:7]=[C:8]([CH3:10])[CH:9]=1>CO.C(OCC)(=O)C>[C:28]([C:24]1[CH:23]=[C:22]([CH2:21][S:20][C:15]2[C:14]([C:12]([NH:11][C:6]3[CH:7]=[C:8]([CH3:10])[CH:9]=[C:4]([CH3:3])[CH:5]=3)=[O:13])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:27]=[CH:26][N:25]=1)([OH:30])=[O:29]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10070822HCID 10070822, compound

Product 1

HCID 23093762HCID 23093762, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1N aqueous sodium hydroxide solution (0.5 mL) was added to a solution of N-(3,5-dimethylphenyl)-2-(2-ethoxycarbonylpyridin-4-ylmethylthio)pyridine-3-carboxamide (95 mg, 0.22 mmol, Compound No. 1-241) in methanol (2 mL), then the mixture was stirred at room temperature for 1.5 hours. 1N hydrochlroric acid (1 mL) was added to the reaction mixture, and this mixture was diluted with ethyl acetate (35 mL). The mixture was washed with brine (20 mL), and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, then the resulting residue was filtered off. The solid was washed with diethyl ether, and then dried at 50° C. under reduced pressure to give 74 mg of the target compound as an orange solid. (Yield 84%)

Workup

  1. washThe mixture was washed with brine (20 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe resulting residue was filtered off
  5. washThe solid was washed with diethyl ether
  6. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-e0ca86491ddd4577b30e179edb9f17ac
Source dataset
uspto-grants-2009_05
Patent number
US07534802B2

Reaction notes

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