N-(5-(7-(benzyloxy)quinolin-4-yloxy)pyridin-2-yl)-N-phenylcyclopropane-1,1-dicarboxamide → N-(5-(7-hydroxyquinolin-4-yloxy)pyridin-2-yl)-N-phenylcyclopropane-1,1-dicarboxamide

HRID 1969428Notes

Reaction equation

HRID 1969428 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:27]([C:29]4([C:32]([NH2:34])=[O:33])[CH2:31][CH2:30]4)=[O:28])=[N:24][CH:25]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:27]([C:29]4([C:32]([NH2:34])=[O:33])[CH2:31][CH2:30]4)=[O:28])=[N:24][CH:25]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 67299422N-(5-(7-(benzyloxy)quinolin-4-yloxy)pyridin-2-yl)-N-phenylcyclopropane-1,1-dicarboxamide

Product 1

HCID 136381440N-(5-(7-hydroxyquinolin-4-yloxy)pyridin-2-yl)-N-phenylcyclopropane-1,1-dicarboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(5-(7-(benzyloxy)quinolin-4-yloxy)pyridin-2-yl)-N-phenylcyclopropane-1,1-dicarboxamide (1.22 g, 2.3 mmol) and Pd/C (1.2 g) in methanol (30 mL) under H2 was stirred at room temperature for 2 hrs, then the reaction mixture was filtered and washed with methanol (10 mL×3). The combined solvent was concentrated in vacuo to give N-(5-(7-hydroxyquinolin-4-yloxy)pyridin-2-yl)-N-phenyl-cyclopropane-1,1-dicarboxamide as a white solid (910.8 mg, 90%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with methanol (10 mL×3)
  3. concentrationThe combined solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-4610a13768b74c40a488ec40aaefbe47
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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