Hydrochloric Acid → HCID 24803118, compound

HRID 2094223Notes

Reaction equation

HRID 2094223 reaction equation
C([O:3][C:4]([C:6]1[N:10]([C:11]2[CH:15]=[CH:14][O:13][N:12]=2)[C:9]([C:16]2[C:21]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=3)(=[O:25])=[O:24])=[CH:20][C:19]([Cl:37])=[CH:18][N:17]=2)=[N:8][N:7]=1)=O)C.[BH4-].[Li+].CO.Cl>C1COCC1>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([NH:22][C:21]2[C:16]([C:9]3[N:10]([C:11]4[CH:15]=[CH:14][O:13][N:12]=4)[C:6]([CH2:4][OH:3])=[N:7][N:8]=3)=[N:17][CH:18]=[C:19]([Cl:37])[CH:20]=2)(=[O:25])=[O:24])=[CH:27][C:28]=1[C:33]([F:36])([F:35])[F:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4148881Lithium borohydrideHCID 24804763HCID 24804763, compound

Product 1

HCID 24803118HCID 24803118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[5-Chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-4-isoxazol-3-yl-4H-[1,2,4]triazole-3-carboxylic acid ethyl ester (28 mg, 0.05 mmol), 0.14 ml (0.28 mmol) of lithium borohydride (2.0M) and 0.020 ml of methanol in 1.5 ml of THF was stirred at room temperature for 2 hours. The mixture was mixed with diluted HCl (1.0M), extracted with ethyl acetate, and the extracts were combined and washed with brine and dried. After concentration the residue was purified by prep TLC to afford title compound as a white solid. MS (ES) [M+H]+ expected 535.0. found 535.0

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. customdried
  4. concentrationAfter concentration the residue
  5. customwas purified by prep TLC

Sources & evidence

ORD record
ord-d09648a823654c4ea1fc960b5dc892d9
Source dataset
uspto-grants-2013_05
Patent number
US08445518B2

Reaction notes

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