Hydrazine hydrate (1:1) → HCID 25262625, compound

HRID 2088485Notes

Reaction equation

HRID 2088485 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[C:10]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][C@@H:28]2[CH3:33])[C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21](F)=[C:22]([CH:25]=3)C#N)=[N:14][C:12]=2[N:13]=1.O.[NH2:35]N>CCO>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[C:10]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][C@@H:28]2[CH3:33])[C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:25]=[C:22]([NH2:35])[CH:21]=[CH:20][CH:19]=3)=[N:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57441872HCID 57441872, compound

Product 1

HCID 25262625HCID 25262625, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0.3M solution of 5-[2,4-bis-((S)-3-methyl-morpholin-4-yl)-pyrido[2,3-d]pyrimidin-7-yl]-2-fluoro-benzonitrile (example lay) (1 equiv) in EtOH was added hydrazine hydrate (5 equiv). The mixture was refluxed for 90 minutes whereupon it was cooled and partitioned between CH2Cl2 and water (1 reaction volume of each). The organic extract was removed. The aqueous phase was further extracted with CH2Cl2 (2×1 reaction volume). The combined organic extracts were then dried (MgSO4), filtered and concentrated in vacuo to give a yellow slurry which was further purified by flash chromatography (SiO2) using EtOAC/Hexanes as eluent to give the title compound as a yellow powder.

Workup

  1. temperatureThe mixture was refluxed for 90 minutes whereupon it
  2. temperaturewas cooled
  3. custompartitioned between CH2Cl2 and water (
  4. custom1 reaction volume of each)
  5. extractionThe organic extract
  6. customwas removed
  7. extractionThe aqueous phase was further extracted with CH2Cl2 (2×1 reaction volume)
  8. dry with materialThe combined organic extracts were then dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give a yellow slurry which
  12. customwas further purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-803cbed80f4e4609945761c964ef77d7
Source dataset
uspto-grants-2013_05
Patent number
US08435985B2

Reaction notes

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