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Trifluoroacetic acid → HCID 22936266, compound

HRID 853467
Notes
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Reaction equation

HRID 853467 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 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-bc77d2fb213c4caf8148e382e2e5fa57
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253286B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes