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Trifluoroacetic acid → HCID 22936266, compound

HRID 387941
Notes
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Reaction equation

HRID 387941 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent

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 stream. 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-b1b75239f4844e2797c859f464c084de
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372981B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes