Maleic Acid → 1-(1-((6-Cyclopropyl-2,4'-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid maleate

HRID 2272541Notes

Reaction equation

HRID 2272541 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH:9]1([C:12]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:16]([F:25])[C:15]([O:26][CH:27]([CH3:29])[CH3:28])=[C:14]([CH2:30][N:31]3[CH2:36][CH2:35][CH:34]([N:37]4[CH:42]=[CH:41][C:40]([C:43]([OH:45])=[O:44])=[C:39]([CH3:46])[C:38]4=[O:47])[CH2:33][CH2:32]3)[CH:13]=2)[CH2:11][CH2:10]1>C(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH:9]1([C:12]2[C:17]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[C:16]([F:25])[C:15]([O:26][CH:27]([CH3:29])[CH3:28])=[C:14]([CH2:30][N:31]3[CH2:32][CH2:33][CH:34]([N:37]4[CH:42]=[CH:41][C:40]([C:43]([OH:45])=[O:44])=[C:39]([CH3:46])[C:38]4=[O:47])[CH2:35][CH2:36]3)[CH:13]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 917546701-(1-((6-Cyclopropyl-2,4'-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Product 1

HCID 1180376001-(1-((6-Cyclopropyl-2,4'-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid maleateYield 91.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Maleic acid (111 mg) was added to a solution of 1-(1-((6-cyclopropyl-2,4′-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (513 mg) in ethanol (5 mL) at room temperature. The mixture was stirred at the same temperature under nitrogen atmosphere for 1 hour and concentrated in vacuo. The residue was crystallized from ethyl acetate-hexane to give a colorless solid. The solid was recrystallized from ethanol-heptane to give the title compound (573 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was crystallized from ethyl acetate-hexane
  3. customto give a colorless solid
  4. customThe solid was recrystallized from ethanol-heptane

Sources & evidence

ORD record
ord-11d3c1b54e584637aad48b9553be58ba
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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