Hydrochloric Acid → HCID 66783111, compound

HRID 1096043Notes

Reaction equation

HRID 1096043 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:33])[C:19]([OH:32])([C:24]3[CH:29]=[CH:28][C:27](=[O:30])[N:26]([CH3:31])[CH:25]=3)[C:20]([F:23])([F:22])[F:21])=[C:14]([Cl:34])[C:13]=2[Cl:35])=[CH:7][N:6]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1>[Cl:35][C:13]1[C:14]([Cl:34])=[C:15]([CH:18]([CH3:33])[C:19]([OH:32])([C:24]2[CH:29]=[CH:28][C:27](=[O:30])[N:26]([CH3:31])[CH:25]=2)[C:20]([F:23])([F:21])[F:22])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66782416HCID 66782416, compound

Product 1

HCID 66783111HCID 66783111, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-{2,3-Dichloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-pyrazine-2-carboxylic acid methyl ester (Example 237; 160 mg, 0.3 mmol) in 1.2 ml THF was treated with 0.6 ml 1N aqueous NaOH and stirred at rt for 2 h. After addition of 1 ml 1N HCl, the reaction mixture was extracted twice with ethyl acetate and the combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered off and concentrated in vacuo to give 156 mg of the title compound as a white solid. MS (M+H+)=518.1

Workup

  1. extractionthe reaction mixture was extracted twice with ethyl acetate
  2. washthe combined organic phases were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e868641208a4d85a465c32078d76eac
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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