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Methanol → HCID 70657042, compound

HRID 69004
Notes
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Reaction equation

HRID 69004 reaction equation
[OH-].[Na+].CO.C[O:6][C:7](=[O:42])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[N:36]([CH3:40])[C:35](=[O:41])[CH:34]=[CH:33]3)[CH2:16][CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:10][CH:9]=1.O>C(O)(=O)C>[CH3:40][N:36]1[C:37]2[C:32](=[CH:31][C:30]([O:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][N:15]([CH2:14][C:11]3[CH:12]=[CH:13][C:8]([C:7]([OH:42])=[O:6])=[CH:9][CH:10]=3)[CH2:16][CH2:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:39][CH:38]=2)[CH:33]=[CH:34][C:35]1=[O:41]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 706568124-{[[5-(1-Methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-(2-pyridin-3-ylethyl)amino]methyl}benzoic acid methyl ester

Product 1

HCID 70657042HCID 70657042, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
50 °C

Procedure

A 1N-sodium hydroxide aqueous solution (0.72 ml) was added to a methanol solution (2 ml) of 4-{[[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-(2-pyridin-3-ylethyl)amino]methyl}benzoic acid methyl ester (153 mg). The mixture was stirred at 50° C. for 3 hours. The reaction mixture was condensed under reduced pressure. Water was added to the residue, and acetic acid was added for neutralization. The mixture was extracted using dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure. Diisopropyl ether was added to the residue. The generated insoluble matter was separated by filtration and dried to give the title compound (115 mg) as a white powder.

Workup

  1. customcondensed under reduced pressure
  2. additionwas added for neutralization
  3. extractionThe mixture was extracted
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure
  5. additionDiisopropyl ether was added to the residue
  6. customThe generated insoluble matter was separated by filtration
  7. customdried

Sources & evidence

ORD record
ord-b101c4c591fb4d5ea57b9224c09adda8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822453B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes