Sodium Hydroxide → HCID 24857232, compound

HRID 551849Notes

Reaction equation

HRID 551849 reaction equation
C([O:3][C:4](=[O:40])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13](=[O:39])[N:14]([CH3:38])[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:36])[C:26]4[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=4)[C:19]=3[CH3:37])[CH:17]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([C:25]([NH:24][C:20]2[C:19]([CH3:37])=[C:18]([C:16]3[CH:17]=[C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:40])=[O:3])=[CH:6][CH:7]=4)[C:13](=[O:39])[N:14]([CH3:38])[CH:15]=3)[CH:23]=[CH:22][CH:21]=2)=[O:36])=[CH:31][CH:30]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 593748354-{5-[3-(4-tert-Butyl-benzoylamino)-2-methylphenyl]-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino}-benzoic acid ethyl ester

Product 1

HCID 24857232HCID 24857232, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-{5-[3-(4-tert-butyl-benzoylamino)-2-methylphenyl]-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino}-benzoic acid ethyl ester (6) (460 mg; 0.86 mmol), 1N NaOH (10 mL), and ethanol (10 mL) was heated at reflux for 1.5 h. The mixture was cooled to room temperature, the resulting slurry was washed with ethyl acetate (2×40 mL), and the ethyl acetate was decanted off. The aqueous slurry was taken to pH 5 with 1N HCl, filtered, washed with water and then diethyl ether to yield 4-{5-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino}-benzoic acid (7) as a light brown solid (248 mg), MS 510.34 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. washthe resulting slurry was washed with ethyl acetate (2×40 mL)
  4. customthe ethyl acetate was decanted off
  5. filtrationfiltered
  6. washwashed with water

Sources & evidence

ORD record
ord-eb130eecf91f4cfb8ea7d0b1b5ca9801
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

Loading…