Hydrochloric Acid → HCID 69001819, compound

HRID 230808Notes

Reaction equation

HRID 230808 reaction equation
[OH-].[Na+].[F:3][C:4]([F:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14]C)=[O:13])=[CH:8][CH:7]=1.Cl>CO>[F:22][C:4]([F:3])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68997700HCID 68997700, compound

Product 1

HCID 69001819HCID 69001819, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 4 N sodium hydroxide solution (300 μL) was added to a methanol solution (5 mL) of methyl 4-(2,2-difluoro-2-pyridin-2-ylethyl)benzenecarboxylate (90 mg) obtained in Production Example 21-2, and stirred at room temperature for 3 hours. The reaction liquid was neutralized with aqueous 1 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to obtain a crude product of 4-(2,2-difluoro-2-pyridin-2-ylethyl)benzenecarboxylic acid. Next, diisopropylethylamine (86 μL) was added to a DMF (5 mL) solution of the obtained carboxylic acid, the compound (61 mg) obtained in Production Example 39-4 and HATU (94 mg), and stirred at room temperature for 4 hours. Water was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, and then dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform/methanol=90/1) to obtain the entitled compound (20 mg) as a white solid.

Workup

  1. customobtained in Production Example 21-2
  2. customThe reaction liquid
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d84606f9368d4902a48425678d8bfa39
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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