Oxalic Acid → 5-Chloro-N-({1-[(4-hydroxytetrahydro-2H-pyran-4-YL)methyl]piperidin-4-YL}methyl)-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide ethanedioate

HRID 2425749Notes

Reaction equation

HRID 2425749 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:16]([NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]3([OH:33])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH2:22][CH2:21]1)=[O:17])[C:6](=[O:15])[N:7]2[CH:12]([CH3:14])[CH3:13].[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36]>CO>[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36].[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:16]([NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]3([OH:33])[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[CH2:22][CH2:21]1)=[O:17])[C:6](=[O:15])[N:7]2[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 533569805-Chloro-N-({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

Product 1

HCID 867613405-Chloro-N-({1-[(4-hydroxytetrahydro-2H-pyran-4-YL)methyl]piperidin-4-YL}methyl)-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide ethanedioateYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-chloro-N-({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide (27 mg, 0.057 mmol, example 1) and oxalic acid (5.2 mg, 0.057 mmol) was dissolved in methanol and stirred for 1 h. The mixture was concentrated and crystallized from diisopropyl ether to give 6.5 mg (20%) of the title compound as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-459886102ab04256a845a929c9e3a89f
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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