Sodium Sulfate → HCID 59428115, compound

HRID 1480924Notes

Reaction equation

HRID 1480924 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:10]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([S:19]([NH:18][C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[N:9]2[CH:10]=[C:6]([CH2:4][OH:3])[CH:7]=[N:8]2)(=[O:21])=[O:20])=[CH:27][CH:26]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 25134745HCID 25134745, compound

Product 1

HCID 59428115HCID 59428115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of 1-[2-(4-tert-butyl-benzenesulfonylamino)-5-chloro-phenyl]-1H-pyrazole-4-carboxylic acid ethyl ester (synthesized according to general procedure D, 220 mg, 0.47 mmol) in THF (5 mL) was added LiAlH4 (1.0 mL, 2.4 M solution in THF) dropwise and the resultant reaction mixture was stirred for one hour at room temperature. Saturated Na2SO4 solution (3 mL) was subsequently added slowly at 0° C. and the precipitated solid was filtered through celite and washed thoroughly with EtOAc (100 mL). The filtrate was dried over Na2SO4, concentrated in vacuo, and purified by automated flash chromatography to afford the title compound: MS (ES) M+H expected 420.1, found 420.1.

Workup

  1. customthe resultant reaction mixture
  2. filtrationthe precipitated solid was filtered through celite
  3. washwashed thoroughly with EtOAc (100 mL)
  4. dry with materialThe filtrate was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by automated flash chromatography

Sources & evidence

ORD record
ord-808e2affe6464d12b5ca439452d084cf
Source dataset
uspto-grants-2016_08
Patent number
US09409909B2

Reaction notes

Loading…