Trifluoroacetic acid → HCID 22936266, compound

HRID 1433600Notes

Reaction equation

HRID 1433600 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])=[CH:18][CH:17]=1)#[N:2].[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>C(O)C.O1CCCC1.[C].[Pd]>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:24])=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22936478HCID 22936478, compound

Product 1

HCID 22936266HCID 22936266, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving the N-[4-(6-cyano-7-methoxyquinolin-4-yloxy)phenyl]-N′-phenylurea (100 mg) synthesized in Example 37 in an ethanol (5 ml) and tetrahydrofuran (5 ml) mixed solvent, there were added trifluoroacetic acid (0.5 ml) and 50% palladium-carbon (50 mg), and the mixture was stirred overnight under a hydrogen atmosphere. After filtering off the palladium carbon, the filtrate was concentrated. The obtained residue was washed with tetrahydrofuran to obtain the title compound (70 mg).

Workup

  1. additionmixed solvent, there
  2. filtrationAfter filtering off the palladium carbon
  3. concentrationthe filtrate was concentrated
  4. washThe obtained residue was washed with tetrahydrofuran

Sources & evidence

ORD record
ord-07961b67ba6f4966ad7a4040f9773d7a
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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