Sulfuric Acid → HCID 59303029, compound

HRID 1692138Notes

Reaction equation

HRID 1692138 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=2[C:23]2[N:27]([CH3:28])[C:26]([CH:29]3CCC[O:31][CH2:30]3)=[N:25][N:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].OS(O)(=O)=O>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=2[C:23]2[N:27]([CH3:28])[C:26]([CH2:29][CH2:30][OH:31])=[N:25][N:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 24992254HCID 24992254, compound

Product 1

HCID 59303029HCID 59303029, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 25 mL scintillation vial was charged with {5-[2-(4-tert-butyl-benzenesulfonylamino)-5-chloro-4-fluoro-phenyl]-4-methyl-4H-[1,2,4]triazol-3-yl}-acetic acid ethyl ester (synthesized according to general procedure P, 95 mg, 0.186 mmol) in 2 mL of anhydrous MeOH. To this solution under a nitrogen atmosphere was added of lithium aluminum hydride (14 mg, 0.372 mmol) at room temperature. LCMS indicated completion of the reaction after 30 minutes and 1 mL of 20% H2SO4 was added. The solvent was subsequently removed in vacuo and the residue was extracted with DCM. The organic layer was then washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The resultant residue was purified via automated silica gel chromatography to afford 4-tert-butyl-N-{4-chloro-5-fluoro-2-[5-(2-hydroxy-ethyl)-4-methyl-4H-[1,2,4]triazol-3-yl]-phenyl}-benzenesulfonamide as a white powder: MS (ES) M+H expected 467.1, found 467.4.

Workup

  1. customcompletion of the reaction after 30 minutes
  2. customThe solvent was subsequently removed in vacuo
  3. extractionthe residue was extracted with DCM
  4. washThe organic layer was then washed with saturated NaHCO3 and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified

Sources & evidence

ORD record
ord-4dd3622ad86543e88b2729869d8db765
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

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