Hydrazine hydrate (1:1) → HCID 70999583, compound

HRID 1878526Notes

Reaction equation

HRID 1878526 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.O.[NH2:24][NH2:25]>C(O)C>[CH:15](=[N:24][NH:25][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)3×HCID 585311415-Chloro-7-(4-morpholinyl)-2-phenylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 70999583HCID 70999583, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidine (51.4 mg, 0.163 mM) was suspended in ethanol (1 mL) and then hydrazine monohydrate (15.8 μL, 0.326 mM) was added to the resulting suspension. This suspension was stirred for 2 hours and a half, while refluxing with heating, then hydrazine monohydrate (15.8 μL, 0.326 mM) was further added to the suspension, the mixture was stirred for additional 3 hours, hydrazine monohydrate (15.8 μL, 0.326 mM) was further added to the mixture and then the mixture was stirred for 18 hours. This reaction liquid was diluted with a saturated aqueous common salt solution and extracted with ethyl acetate. The extracts thus obtained were combined, dried over anhydrous sodium sulfate and the solvent was then distilled off. The resulting residue was suspended in ethanol (0.5 mL), then acetic acid (2.0 μL, 0.035 mM) and benzaldehyde (16.6 μL, 0.196 mM) were added to the suspension and the mixture was stirred at room temperature for 15 minutes. This reaction mixture was filtered and the resulting solid was purified by the NH-silica gel column chromatography (methylene chloride) to thus give the title compound (16.5 mg, overall yield of these two steps: 25%).

Workup

  1. temperaturea half, while refluxing
  2. temperaturewith heating
  3. stirringthe mixture was stirred for additional 3 hours
  4. stirringthe mixture was stirred for 18 hours
  5. customThis reaction liquid
  6. additionwas diluted with a saturated aqueous common salt solution
  7. extractionextracted with ethyl acetate
  8. customThe extracts thus obtained
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was then distilled off
  11. additionacetic acid (2.0 μL, 0.035 mM) and benzaldehyde (16.6 μL, 0.196 mM) were added to the suspension
  12. stirringthe mixture was stirred at room temperature for 15 minutes
  13. filtrationThis reaction mixture was filtered
  14. customthe resulting solid was purified by the NH-silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-fc1b2816d0f74b34a4f678fb3dc07302
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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