Water → HCID 22372116, compound

HRID 725828Notes

Reaction equation

HRID 725828 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[N:8]2[N:26]=[C:27]([CH3:29])[CH:28]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].C1C(=O)N([Cl:37])C(=O)C1.O>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12](=[O:25])[C:13]2[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)[N:8]2[N:26]=[C:27]([CH3:29])[C:28]([Cl:37])=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 9801000HCID 9801000, compound

Product 1

HCID 22372116HCID 22372116, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-n-Butyl-2-methyl-7-(3,4,5-trimethoxybenzoyl-amino) pyrazolo[1,5-a]pyrimidine (the compound of Example 53; 0.78 g) was dissolved in 10 ml of chloroform. After addition of 0.28 g of NCS, the mixture was refluxed with heating for 1 hour and allowed to cool. After addition of some water, the reaction mixture was extracted with chloroform. The organic layer was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:2) and recrystallized from ethanol-n-hexane to provide 0.61 g of the object compound as colorless crystals. Table 3 shows the structure and melting point of the compound obtained.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 1 hour
  3. temperatureto cool
  4. extractionthe reaction mixture was extracted with chloroform
  5. customThe organic layer was collected
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:2)
  9. customrecrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-82c3d8fbe349412bb2d3f382278ecd0c
Source dataset
uspto-grants-1998_01
Patent number
US05707997

Reaction notes

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