Maleic Acid → 6-(1-((2-Cyclopropyl-5-ethoxy-2',4'-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylic acid maleate

HRID 531150Notes

Reaction equation

HRID 531150 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH:9]1([C:12]2[CH:17]=[C:16]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([N:25]4[CH2:34][CH2:33][C:32]5[N:31]=[C:30]([CH2:35][CH2:36][CH3:37])[C:29]([C:38]([OH:40])=[O:39])=[CH:28][C:27]=5[C:26]4=[O:41])[CH2:21][CH2:20]3)[C:15]([O:42][CH2:43][CH3:44])=[CH:14][C:13]=2[C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:46]=2[F:52])[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[CH:17]=[C:16]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([N:25]4[CH2:34][CH2:33][C:32]5[N:31]=[C:30]([CH2:35][CH2:36][CH3:37])[C:29]([C:38]([OH:40])=[O:39])=[CH:28][C:27]=5[C:26]4=[O:41])[CH2:21][CH2:20]3)[C:15]([O:42][CH2:43][CH3:44])=[CH:14][C:13]=2[C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:46]=2[F:52])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 1179922906-(1-((2-Cyclopropyl-5-ethoxy-2',4'-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylic acid

Product 1

HCID 1179922896-(1-((2-Cyclopropyl-5-ethoxy-2',4'-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylic acid maleateYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Maleic acid (36.1 mg) was added to a mixture of 6-(1-((2-cyclopropyl-5-ethoxy-2′,4′-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylic acid (125 mg) in ethanol (10 mL). The suspension was filtered and the solvent was removed under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give the title compound (100 mg).

Workup

  1. filtrationThe suspension was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f4479b3e12b14ca0be645b8817764206
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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