Sodium Hydroxide → N-(3-fluoro-4-(7-((1-hydroxycyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

HRID 1517909Notes

Reaction equation

HRID 1517909 reaction equation
C([O:9][C:10]1([CH2:13][O:14][C:15]2[CH:24]=[C:23]3[C:18]([C:19]([O:25][C:26]4[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]5([C:38](=[O:40])[NH2:39])[CH2:37][CH2:36]5)=[O:34])=[CH:28][C:27]=4[F:41])=[CH:20][CH:21]=[N:22]3)=[CH:17][C:16]=2[O:42][CH3:43])[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[F:41][C:27]1[CH:28]=[C:29]([N:32]([C:30]2[CH:29]=[CH:28][C:27]([F:41])=[CH:26][CH:31]=2)[C:33]([C:35]2([C:38]([NH2:39])=[O:40])[CH2:36][CH2:37]2)=[O:34])[CH:30]=[CH:31][C:26]=1[O:25][C:19]1[C:18]2[C:23](=[CH:24][C:15]([O:14][CH2:13][C:10]3([OH:9])[CH2:12][CH2:11]3)=[C:16]([O:42][CH3:43])[CH:17]=2)[N:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 666698591-((4-(4-(1-(Carbamoyl)cyclopropanecarboxamido)-2-fluorophenoxy)-6-methoxyquinolin-7-yloxy)methyl)cyclopropyl benzoate

Product 1

HCID 68740489N-(3-fluoro-4-(7-((1-hydroxycyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamideYield 153.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-((4-(4-(1-(carbamoyl)cyclopropanecarboxamido)-2-fluorophenoxy)-6-methoxyquinolin-7-yloxy)methyl)cyclopropyl benzoate (800 mg, 1.178 mmol) in CH3OH (10 mL) was added aqueous NaOH (94 mg, 2.356 mmol) solution (5 mL). The reaction was stirred at rt overnight. The suspension was concentrated, and the residual was purified by a silica gel column chromatography (EtOAc to 100:1 (v/v) EtOAc/CH3OH) to give the title product as a white solid (520 mg, 77%).

Workup

  1. concentrationThe suspension was concentrated
  2. customthe residual was purified by a silica gel column chromatography (EtOAc to 100:1 (v/v) EtOAc/CH3OH)

Sources & evidence

ORD record
ord-3d42e165fdc04e348a23531f5087b45b
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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