Methyl 5-methoxy-3-oxopentanoate → HCID 178494792, compound

HRID 636431Notes

Reaction equation

HRID 636431 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][CH2:21][C:22](=O)[CH2:23][C:24]([O:26][CH3:27])=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][CH2:24][O:26][CH3:27])=[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 542416Methyl 5-methoxy-3-oxopentanoateHCID 110547174-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine

Product 1

HCID 178494792HCID 178494792, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.69 g (10 mmol) of) 4-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine and 1.6 g (10 mmol) of methyl 5-methoxy-3-oxo-valerate in 10 ml of acetic acid was heated at reflux for 4 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 20:1) yielded 2.40 g (61%) of 3-benzenesulphonyl-5-(2-methoxy-ethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol as a beige powder.

Workup

  1. temperatureat reflux for 4 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-a7f256e765f74f1fb1433246f2979beb
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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