Hydrazine → HCID 11963015, compound

HRID 2359680Notes

Reaction equation

HRID 2359680 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][N:14]1[C:18]([CH3:19])=[C:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[C:39]4[C:34](=[CH:35][C:36]([O:40][CH3:41])=[CH:37][CH:38]=4)[N:33]=[CH:32][CH:31]=3)=[C:25]([F:42])[CH:24]=2)=[O:21])[C:16](=[O:43])[N:15]1[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.O.CCO.NN.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:3][CH2:12][CH2:13][N:14]1[C:18]([CH3:19])=[C:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[C:39]4[C:34](=[CH:35][C:36]([O:40][CH3:41])=[CH:37][CH:38]=4)[N:33]=[CH:32][CH:31]=3)=[C:25]([F:42])[CH:24]=2)=[O:21])[C:16](=[O:43])[N:15]1[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 11963016HCID 11963016, compoundHCID 19096565Water ethanol

Product 1

HCID 11963015HCID 11963015, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-N-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (0.20 g, 0.30 mmol) in 1:1 H2O/EtOH was added hydrazine (0.049 g, 1.5 mmol). The reaction was heated to 50° C. for 8 hours and then cooled to RT. The reaction mixture was then diluted with 20 mL of satd. NaHCO3 aq. solution and 60 mL of EtOAc. The organic phase was separated and washed with 30 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was washed with 20% hexane in EtOAc to give the title compound as a light yellow solid (0.13 g, 81% yield).

Workup

  1. temperaturecooled to RT
  2. additionThe reaction mixture was then diluted with 20 mL of satd
  3. customThe organic phase was separated
  4. washwashed with 30 mL of brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with 20% hexane in EtOAc

Sources & evidence

ORD record
ord-ee51996a6326472ba4dd03d8d147d909
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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