Water → HCID 117770817, compound

HRID 1526343Notes

Reaction equation

HRID 1526343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13]([C:14]#[N:15])=[CH:12][C:11]2[NH:16][N:17]=[C:18]([N:19]3C(=O)C4C(=CC=CC=4)C3=O)[C:10]=2[C:9]1=[O:30].O.NN.O>C(O)C>[NH2:19][C:18]1[C:10]2[C:9](=[O:30])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:13]([C:14]#[N:15])=[CH:12][C:11]=2[NH:16][N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 117770120HCID 117770120, compound

Product 1

HCID 117770817HCID 117770817, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(2-chlorophenyl)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-6-carbonitrile obtained in Step K (203 mg) in ethanol (1.63 mL) was added hydrazine monohydrate (29.3 mg) at room temperature. The reaction mixture was stirred at 50° C. for 20 min, and cooled to room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water 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 (methanol/dichloromethane) to give the title compound (105 mg).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methanol/dichloromethane)

Sources & evidence

ORD record
ord-5809f8f6b3534bcc9830656fbab10f75
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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