Methylhydrazine → HCID 67395757, compound

HRID 1822198Notes

Reaction equation

HRID 1822198 reaction equation
O[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[C:19](=O)[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.[CH3:29][NH:30][NH2:31]>C(O)C>[CH3:29][N:30]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[N:7][C:6]=3[N:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4](=[O:18])[C:3]=2[C:19]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[N:31]1

Participants

4

Reactant 2

HCID 6061Methylhydrazine2×HCID 54676197HCID 54676197, compound

Product 1

HCID 67395757HCID 67395757, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-hydroxy-3-[1-oxo-3-(pyridin-4-yl)propyl]-1-phenyl-1,8-naphthyridin-2 (1H)-one (100 mg, 0.27 mmol, prepared in Synthetic Example 1) in ethanol (2 ml) was added methylhydrazine (40 μl, 0.75 mmol, 2.8 eq.) and the mixture was stirred at room temperature to form a solution which was then stirred for 30 minutes. After it was perceived that precipitation started, the mixture was heated under reflux for 3 hours and cooled to room temperature. Next, to the liquid mixture was added additional methylhydrazine (40 μl, 0.75 mmol, 2.8 eq.) and the resultant mixture was heated overnight with stirring at 70° C. The liquid reaction mixture was cooled to room temperature, and then filtered to give precipitates which were dried to obtain 1-methyl-5-phenyl-3-[2-(pyridin-4-yl)ethyl]-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (94 mg, 92%).

Workup

  1. customto form a solution which
  2. stirringwas then stirred for 30 minutes
  3. customAfter it was perceived that precipitation
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 3 hours
  6. temperaturecooled to room temperature
  7. stirringwith stirring at 70° C
  8. customThe liquid reaction mixture
  9. temperaturewas cooled to room temperature
  10. filtrationfiltered
  11. customto give
  12. customprecipitates which
  13. customwere dried

Sources & evidence

ORD record
ord-9064b7932cb448afa6fbfbcd9df7eab8
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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