Sodium Hydroxide → 5-(2-Hydroxyethyl)-4-methyl-N-{[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}thiophene-2-sulfonamide

HRID 1696782Notes

Reaction equation

HRID 1696782 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([S:13]([NH:16][C:17](=[O:30])[NH:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([CH3:29])[N:20]=2)(=[O:15])=[O:14])=[CH:10][C:11]=1[CH3:12])(=O)C.[OH-].[Na+]>CO>[OH:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([S:13]([NH:16][C:17](=[O:30])[NH:18][C:19]2[CH:24]=[C:23]([C:25]([F:27])([F:28])[F:26])[CH:22]=[C:21]([CH3:29])[N:20]=2)(=[O:15])=[O:14])=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 426288892-{3-Methyl-5-[({[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}amino)sulfonyl]-2-thienyl}ethyl acetate

Product 1

HCID 426288915-(2-Hydroxyethyl)-4-methyl-N-{[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}thiophene-2-sulfonamideYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.25 g 2-{3-methyl-5-[({[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}amino)sulfonyl]-2-thienyl}ethyl acetate in 5 ml methanol was added 0.01 ml 28% aqueous sodium hydroxide and the mixture was kept at room temperature for 3 h. The reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was washed with brine and evaporated. The residue was triturated with t-butylmethyl ether/heptane to yield 0.177 g of the title compound as off white powder MS (ISN) M−H+=422.4.

Workup

  1. customThe reaction mixture was partitioned between 10% citric acid and ethyl acetate
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. customevaporated
  5. customThe residue was triturated with t-butylmethyl ether/heptane

Sources & evidence

ORD record
ord-6efdcdb72bd448bbb62fab00f83fd978
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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