Hydrazine hydrate (1:1) → HCID 117769950, compound

HRID 1526404Notes

Reaction equation

HRID 1526404 reaction equation
[Br:1][C:2]1[C:3](Cl)=[C:4]([C:14]#[N:15])[C:5](=O)[N:6]([C@H:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[CH:7]=1.[OH2:17].[NH2:18][NH2:19]>C(O)C>[NH2:15][C:14]1[C:4]2[C:5](=[O:17])[N:6]([C@H:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[CH:7]=[C:2]([Br:1])[C:3]=2[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117770455HCID 117770455, compound

Product 1

HCID 117769950HCID 117769950, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-4-chloro-1-((2S)-3-methylbutan-2-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step F (19.2 g) in ethanol (200 mL) was added hydrazine monohydrate (9.5 g), and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was allowed to be cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in a mixed solvent of ethyl acetate-tetrahydrofuran-water. The organic layer was separated, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane, and then ethyl acetate/methanol), and recrystallized from (ethyl acetate/diisopropyl ether) to give the title compound (15.5 g).

Workup

  1. temperatureto be cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixed solvent of ethyl acetate-tetrahydrofuran-water
  4. customThe organic layer was separated
  5. washwashed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane
  9. customethyl acetate/methanol), and recrystallized from (ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-2bf87d014bc043748884b1510d76c6aa
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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