Lithium borohydride → 5-(2-Hydroxyethyl)-N-{[6-(hydroxymethyl)-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}-4-methylthiophene-2-sulfonamide

HRID 1696776Notes

Reaction equation

HRID 1696776 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](OC)=[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.[BH4-].[Li+]>O1CCCC1>[OH:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([S:12]([NH:15][C:16](=[O:17])[NH:18][C:19]2[CH:20]=[C:21]([C:29]([F:31])([F:32])[F:30])[CH:22]=[C:23]([CH2:25][OH:26])[N:24]=2)(=[O:14])=[O:13])=[CH:9][C:8]=1[CH3:33]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 42630611Methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate

Product 1

HCID 672743805-(2-Hydroxyethyl)-N-{[6-(hydroxymethyl)-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}-4-methylthiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 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 tetrahydrofuran was added 0.02 g lithiumborohydride and the mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated. The organic phase was washed with water. To he combined water phases was added 1 ml 10% citric acid and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and evaporated to yield the title compound as white foam (containing acetoxy and hydroxyethyl ca 1:1) The mixture was dissolved in ca 2 ml methanol and ca 0.05 ml 28% sodium hydroxide and kept at room temperature for 5 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 0.049 g of the title compound as white foam. MS (ISN) M−H+=438.4

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe phases were separated
  3. washThe organic phase was washed with water
  4. additionwas added 1 ml 10% citric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. customevaporated

Sources & evidence

ORD record
ord-7d52fae8c2a04dddb7d5dffcb121197a
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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