4-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine → HCID 178494547, compound

HRID 636434

Reaction equation

HRID 636434 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[O:19][CH2:20][C:21](=O)[CH2:22][C:23]([O:25][CH2:26]C)=O>C(O)(=O)C>[C:1]1([S:7]([C:10]2[C:14]([S:15][CH3:16])=[N:13][N:12]3[C:20]([OH:19])=[CH:21][C:22]([CH2:23][O:25][CH3:26])=[N:17][C:11]=23)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 110547174-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamineHCID 12645099Ethyl 4-methoxy-3-oxobutanoate

Product 1

HCID 178494547HCID 178494547, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.69 g (10 mmol) 4-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine and 1.46 g (10 mmol) of ethyl 4-methoxy-acetoacetate in 10 ml of acetic acid was heated at reflux for 3 hrs. The reaction solution was evaporated and the residue was partitioned between H2O and CH2Cl2. The aqueous phase was extracted three times with 80 ml of CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 25:1) yielded 3.1 g (85%) of 3-benzenesulphonyl-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol as a beige powder, m.p. 175-155°.

Workup

  1. temperatureat reflux for 3 hrs
  2. customThe reaction solution was evaporated
  3. customthe residue was partitioned between H2O and CH2Cl2
  4. extractionThe aqueous phase was extracted three times with 80 ml of CH2Cl2
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-71c13a4487e84535bdbd8749a6661bb8
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Linked notes

Loading…