Hydrochloric Acid → 4-(N-(Benzofuran-5-ylmethyl)-N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoic acid

HRID 73058Notes

Reaction equation

HRID 73058 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([C:32]([F:35])([F:34])[F:33])=[CH:27][N:26]=3)[S:12]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+].Cl>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([C:32]([F:33])([F:35])[F:34])=[CH:27][N:26]=3)[S:12]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66837870methyl 4-(N-(benzofuran-5-ylmethyl)-N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate

Product 1

HCID 569493314-(N-(Benzofuran-5-ylmethyl)-N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-(N-(benzofuran-5-ylmethyl)-N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)sulfamoyl)benzoate (step-2 of Example 1, 2.3 g, 4.3 mmol) in THF (15 mL) was added 2 M aqueous NaOH (9.0 mL) at room temperature, and the mixture was heated at 60° C. for 2 hrs. The mixture was cooled with ice bath, and acidified by the addition of 2 M aqueous HCl (10 mL). The mixture was extracted with DCM (30 mL×2), dried over Na2SO4, filtered and the filtrate was concentrated to give a white solid. The residual solid was triturated with IPE (50 mL), the precipitates were collected by filtration, washed with IPE, and dried in vacuo at 50° C. to give 1.6 g (74% yield) of the titled compound as a white powder.

Workup

  1. temperatureThe mixture was cooled with ice bath
  2. extractionThe mixture was extracted with DCM (30 mL×2)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give a white solid
  7. customThe residual solid was triturated with IPE (50 mL)
  8. filtrationthe precipitates were collected by filtration
  9. washwashed with IPE
  10. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-fde55e4cf992452989d10ddd389e8374
Source dataset
uspto-grants-2014_09
Patent number
US08829026B2

Reaction notes

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