Sodium hydride → Methyl-6-[({[5-(2-hydroxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate

HRID 1696775Notes

Reaction equation

HRID 1696775 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([S:12]([NH:15][C:16]([NH:18][C:19]2[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)=[O:17])(=[O:14])=[O:13])=[CH:9][C:8]=1[CH3:33])(=O)C.[H-].[Na+]>CO>[CH3:28][O:27][C:25]([C:23]1[CH:22]=[C:21]([C:29]([F:31])([F:30])[F:32])[CH:20]=[C:19]([NH:18][C:16](=[O:17])[NH:15][S:12]([C:10]2[S:11][C:7]([CH2:6][CH2:5][OH:4])=[C:8]([CH3:33])[CH:9]=2)(=[O:14])=[O:13])[N:24]=1)=[O:26]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 42630611Methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate

Product 1

HCID 42630724Methyl-6-[({[5-(2-hydroxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 0.100 g methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate in 1.5 ml methanol was added 0.02 g sodium hydride 55% in oil. The resulting solution was stirred at room temperature for 18 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 to yield the title compound as white foam. MS (ISN) M−H+=466.3

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

Sources & evidence

ORD record
ord-8bb789dff0844980a69dbe1faf3b3271
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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