Sodium Hydroxide → 4-{6-[3-(4-tert-Butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid

HRID 551855Notes

Reaction equation

HRID 551855 reaction equation
C([O:3][C:4](=[O:40])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=[C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27](=[O:38])[C:28]4[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=4)[C:21]=3[CH3:39])[N:13]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([C:27]([NH:26][C:22]2[C:21]([CH3:39])=[C:20]([C:14]3[N:13]=[C:12]([NH:11][C:8]4[CH:7]=[CH:6][C:5]([C:4]([OH:40])=[O:3])=[CH:10][CH:9]=4)[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=3)[CH:25]=[CH:24][CH:23]=2)=[O:38])=[CH:29][CH:30]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118525664-{6-[3-(4-tert-Butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid ethyl ester

Product 1

HCID 248572334-{6-[3-(4-tert-Butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acidYield 38.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of give 4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid ethyl ester (6) (300 mg; 0.56 mmol), 1N NaOH (5 mL), and ethanol (5 mL) was heated at reflux for 1 hr. The mixture was cooled to room temperature and 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 give 4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid (7) as a gray solid (110 mg), MS 511.46 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  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-fa80cf547f794209b46937154e56cf08
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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