Hydrazine hydrate (1:1) → HCID 117839662, compound

HRID 1477641Notes

Reaction equation

HRID 1477641 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH:14]=[C:13]1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.O.NN>C(O)C>[NH2:3][CH:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH:14]=[C:13]1[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117839941HCID 117839941, compound

Product 1

HCID 117839662HCID 117839662, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (5.0 mL) of tert-butyl 5-(1,3-dioxoisoindolin-2-yl)-4-(4-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (500 mg, 2.36 mmol) synthesized in Reference Synthesis Example 201, hydrazine monohydrate (177 mg, 7.08 mmol) was added and the resultant mixture was stirred under reflux by heating for 5 hours. After completion of the reaction, the reaction solution was filtered and the filtrate was concentrated under reduced pressure. Chloroform was added to the obtained residue and the resultant mixture was filtered again, followed by concentrating the resultant filtrate under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the title compound (150 mg, yield 22%).

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperatureby heating for 5 hours
  4. customAfter completion of the reaction
  5. filtrationthe reaction solution was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionChloroform was added to the obtained residue
  8. filtrationthe resultant mixture was filtered again
  9. concentrationby concentrating the resultant filtrate under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9d1ac6e547de494ea09b882b56e879a7
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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