Water → HCID 59389399, compound

HRID 2357895Notes

Reaction equation

HRID 2357895 reaction equation
[CH2:1]([C:3]1[CH:13]=[C:6]2[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].C1C(=O)N([Cl:21])C(=O)C1.O>CN(C=O)C>[Cl:21][C:13]1[C:3]([CH2:1][CH3:2])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:6]=12

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 219845782-Ethyl-4-methoxypyrazolo[1,5-a]pyridine

Product 1

HCID 59389399HCID 59389399, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 49 (2.07 g) was dissolved in DMF (60 mL). To this solution, NCS (1.88 g) was added and the mixture was stirred at room temperature for 5.5 hours. Subsequently, water was added and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=3:1) afforded the title compound as a gray powder (2.28 g).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvent
  5. customunder reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a70763205d99471992fafb195b2c2ba9
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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