Acetic Acid → HCID 178470704, compound

HRID 636427Notes

Reaction equation

HRID 636427 reaction equation
[C:1]1([S:7]([C:10]2[C:14]([S:15][CH3:16])=[N:13][NH:12][C:11]=2[NH2:17])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([CH:21]1[CH2:26][CH2:25][O:24][C:22]1=[O:23])(=O)[CH3:19].[OH2:27].[C:28](O)(=O)[CH3:29]>>[C:1]1([S:7]([C:10]2[C:14]([S:15][CH3:16])=[N:13][N:12]3[C:22]([OH:23])=[C:21]([CH2:26][C:25]([O:24][CH2:28][CH3:29])=[O:27])[C:18]([CH3:19])=[N:17][C:11]=23)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 106012-AcetylbutyrolactoneHCID 110547174-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine

Product 1

HCID 178470704HCID 178470704, compoundYield 36%

Procedure

A solution of 2.69 g (10 mmol) of 4-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine and 1.28 g (10 mmol) of 2-acetyl-butyrolactone in 10 ml of acetic acid was heated at reflux for 1.5 hrs. After cooling to RT the mixture was treated with 50 ml of H2O and extracted three times with CH2Cl2. The organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 20:1) of the residue yielded 1.5 g (36%) of ethyl 2-(3-benzenesulphonyl-7-hydroxy-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-6-yl)-acetate as a colorless foam.

Workup

  1. temperatureat reflux for 1.5 hrs
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1da3f4662bc442a1bd074f52e2d50ee7
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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