HCID 22936514, compound → Cabozantinib Impurity

HRID 2277405Notes

Reaction equation

HRID 2277405 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:29][CH3:30])C1C=CC=CC=1.C(O[K])=O>CO.O.CCOC(C)=O.[Pd]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:29][CH3:30])[CH:11]=3)[N:16]=[CH:15][CH:14]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 22936514HCID 22936514, compoundHCID 178526052HCID 178526052, compound

Product 1

HCID 136350300Cabozantinib ImpurityYield 95.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A suspension of 7-(benzyloxy)-6-methoxy-4-(4-nitrophenoxy)quinoline (43.00 g, 120 mmol), 10% Pd/C (4.30 g) and HCOOK (89.93 g, 600 mmol) in MeOH/H2O (345 mL/200 mL) was refluxed overnight. The mixture was cooled to room temperature, diluted with EtOAc (300 mL) and filtered through a celite pad. The filtrate was concentrated in vacuo and the residue was washed with water, dried in vacuo at 60° C. overnight to give the title compound as a yellow solid (28.8 g, 95.5%).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. washthe residue was washed with water
  5. customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-33c131c04b4e46cdb3dde2febe0dfda9
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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