Sodium Hydroxide → 6-(1-((6-Cyclopropyl-3-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

HRID 531093Notes

Reaction equation

HRID 531093 reaction equation
[OH-].[Na+].[CH:3]1([C:6]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([F:19])[C:9]([O:20][CH2:21][CH3:22])=[C:8]([CH2:23][N:24]3[CH2:29][CH2:28][CH:27]([N:30]4[CH2:39][CH2:38][C:37]5[N:36]=[C:35]([CH2:40][CH2:41][CH3:42])[C:34]([C:43]([O:45]CC)=[O:44])=[CH:33][C:32]=5[C:31]4=[O:48])[CH2:26][CH2:25]3)[CH:7]=2)[CH2:5][CH2:4]1>C(O)C>[CH:3]1([C:6]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([F:19])[C:9]([O:20][CH2:21][CH3:22])=[C:8]([CH2:23][N:24]3[CH2:25][CH2:26][CH:27]([N:30]4[CH2:39][CH2:38][C:37]5[N:36]=[C:35]([CH2:40][CH2:41][CH3:42])[C:34]([C:43]([OH:45])=[O:44])=[CH:33][C:32]=5[C:31]4=[O:48])[CH2:28][CH2:29]3)[CH:7]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117992314Ethyl 6-(1-((6-cyclopropyl-3-ethoxy-2,4'-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate

Product 1

HCID 916682496-(1-((6-Cyclopropyl-3-ethoxy-2,4'-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylic acidYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2M aqueous sodium hydroxide solution (25 mL) was added to a solution of ethyl 6-(1-((6-cyclopropyl-3-ethoxy-2,4′-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (7.98 g) in ethanol (65 mL) at room temperature. The mixture was stirred at 80° C. under nitrogen atmosphere for 2 hours and concentrated in vacuo. The residue was dissolved in water. The solution was adjusted to neutral with 2M hydrochloric acid to give colorless crystals. After filtration, the crystals was dissolved in ethanol. The solution was filtrated and the filtrate was concentrated in vacuo. The residue was crystallized from ethyl acetate-hexane to give a colorless solid. The solid was recrystallized from ethanol-hexane to give the title compound (7.16 g).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. customto give colorless crystals
  4. filtrationAfter filtration
  5. dissolutionthe crystals was dissolved in ethanol
  6. filtrationThe solution was filtrated
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was crystallized from ethyl acetate-hexane
  9. customto give a colorless solid
  10. customThe solid was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-dffc6948020849a1b00aee82e0af80a0
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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