Hydrazine hydrate (1:1) → HCID 117839459, compound

HRID 1477644Notes

Reaction equation

HRID 1477644 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C@H:9]([N:14]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.O.NN>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C@H:9]([NH2:14])[CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117839797HCID 117839797, compound

Product 1

HCID 117839459HCID 117839459, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (1.0 mL) of (S)-2-[4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridin-3-yl]isoindoline-1,3-dione (170 mg, 0.402 mmol) synthesized in Reference Synthesis Example 210, hydrazine monohydrate (150 mg, 3.00 mmol) was added and the resultant mixture was stirred under reflux by heating for 2 hours. After completion of the reaction, the reaction solution was filtered and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the obtained residue and the resultant mixture was filtered again, followed by concentrating the resultant filtrate under reduced pressure to obtain the title compound (46.0 mg, yield 59%).

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperatureby heating for 2 hours
  4. customAfter completion of the reaction
  5. filtrationthe reaction solution was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionEthyl acetate was added to the obtained residue
  8. filtrationthe resultant mixture was filtered again
  9. concentrationby concentrating the resultant filtrate under reduced pressure

Sources & evidence

ORD record
ord-b70f86ea68cd41739f8ce4e8d270b9a0
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…