Hydrochloric Acid → HCID 86707382, compound

HRID 878744Notes

Reaction equation

HRID 878744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:30]3[N:31]=[CH:32][C:33]4[C:38]([C:39]=3[CH3:40])=[CH:37][CH:36]=[CH:35][CH:34]=4)[S:16]([C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][N:15]([C:30]3[N:31]=[CH:32][C:33]4[C:38]([C:39]=3[CH3:40])=[CH:37][CH:36]=[CH:35][CH:34]=4)[S:16]([C:19]3[CH:29]=[CH:28][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68289682HCID 68289682, compound

Product 1

HCID 86707382HCID 86707382, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of ethyl 4-{[[(4′-fluorobiphenyl-4-yl)methyl](4-methylisoquinolin-3-yl)amino]sulfonyl}benzoate (88.0 mg, 0.16 mmol) prepared in Example 7 and 1 mol/L aqueous sodium hydroxide solution (320 μl, 0.32 mmol) in methanol (1.6 ml) was stirred at room temperature overnight, and then to the reaction solution was added 2 mol/L hydrochloric acid solution (400 μl). The mixture was extracted with chloroform twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give 4-{[[(4′-fluorobiphenyl-4-yl)methyl](4-methylisoquinolin-3-yl)amino]sulfonyl}benzoic acid (62.1 mg, 74%) as a colorless powder.

Workup

  1. extractionThe mixture was extracted with chloroform twice
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record
ord-78a4a68688264954bf5ac4ce44daeb39
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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