Hydrochloric Acid → HCID 66547443, compound

HRID 878746Notes

Reaction equation

HRID 878746 reaction equation
[CH2:1]([O:3][C:4]([C:10]1[CH:42]=[CH:41][C:13]([CH2:14][N:15]([C:30]2[N:31]=[CH:32][C:33]3[C:38]([C:39]=2[CH3:40])=[CH:37][CH:36]=[CH:35][CH:34]=3)[S:16]([C:19]2[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1)([CH3:9])[C:5]([F:8])([F:7])[F:6])[CH3:2].[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH2:1]([O:3][C:4]([C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]([C:30]2[N:31]=[CH:32][C:33]3[C:38]([C:39]=2[CH3:40])=[CH:37][CH:36]=[CH:35][CH:34]=3)[S:16]([C:19]2[CH:29]=[CH:28][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)(=[O:17])=[O:18])=[CH:41][CH:42]=1)([CH3:9])[C:5]([F:6])([F:7])[F:8])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68289434HCID 68289434, compound

Product 1

HCID 66547443HCID 66547443, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl 4-{[[4-(1-ethoxy-2,2,2-trifluoro-1-methylethyl)benzyl](4-methylisoquinolin-3-yl)amino]sulfonyl}benzoate (102 mg, 0.17 mmol) prepared in Example 13 in ethanol (1 mL) and tetrahydrofuran (1 mL) was added 2 mol/L aqueous sodium hydroxide solution (340 μL, 0.68 mmol) at room temperature. The reaction solution was stirred at room temperature overnight, and then to the reaction solution was added 2 mol/L hydrochloric acid solution (1 ml). The mixture was extracted with chloroform three times. The organic layer was combined, 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→10:1) to give 4-{[[4-(1-ethoxy-2,2,2-trifluoro-1-methylethyl)benzyl](4-methylisoquinolin-3-yl)amino]sulfonyl}benzoic acid (82 mg, 85%) as a colorless powder.

Workup

  1. extractionThe mixture was extracted with chloroform three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→10:1)

Sources & evidence

ORD record
ord-b6966a1fecf24cd199f8a3358fa8a590
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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