Sulfuric Acid → HCID 68275986, compound

HRID 1475948Notes

Reaction equation

HRID 1475948 reaction equation
[CH2:1]([N:6]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:7]([C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:23]([O:25]CC)=[O:24])[C:17](C(OCC)=O)=[C:11]2[CH:10]=1)=[O:8])[CH2:2][CH:3]([CH3:5])[CH3:4].S(=O)(=O)(O)O>>[CH2:28]([N:6]([CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[C:7]([C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:23]([OH:25])=[O:24])[CH:17]=[C:11]2[CH:10]=1)=[O:8])[CH2:29][CH:30]([CH3:32])[CH3:31]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 68275984HCID 68275984, compound

Product 1

HCID 68275986HCID 68275986, compoundYield 106.8%

Procedure

Diethyl 5-(diisopentylcarbamoyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate (0.35 g, 0.786 mmol) was added to 40% aqueous sulphuric acid (5 ml) and stirred at reflux for 3 h. The resulting suspension was cooled in an ice bath then extracted with ethyl acetate (3×25 ml). The combined organic layers were washed with brine and concentrated to afford, 0.29 g (98%) of the title compound as a white solid. LCMS m/z 346.2 (M+H)+. ret. time=2.57 min.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe resulting suspension was cooled in an ice bath
  3. extractionthen extracted with ethyl acetate (3×25 ml)
  4. washThe combined organic layers were washed with brine
  5. concentrationconcentrated
  6. customto afford

Sources & evidence

ORD record
ord-8223ff49aa10441bacd85345baeb6e8f
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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