Sodium Hydroxide → HCID 118037887, compound

HRID 2272538Notes

Reaction equation

HRID 2272538 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[CH:35]=[CH:34][C:33]([C:36]([O:38]C)=[O:37])=[C:32]([CH3:40])[C:31]4=[O:41])[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:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=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[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[C:32]([CH3:40])[C:31]4=[O:41])[CH2:28][CH2:29]3)[CH:7]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118037419HCID 118037419, compound

Product 1

HCID 118037887HCID 118037887, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 M aqueous sodium hydroxide solution (2 mL) was added at room temperature to an ethanol (8 mL) solution of methyl 1-(1-((6-cyclopropyl-3-ethoxy-2,4′-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate (283 mg), and the mixture was stirred at 80 C for 3 hours in a nitrogen atmosphere. Then, the solvent was distilled off under reduced pressure. Water was added to the obtained residue, and the mixture was neutralized with 2 M hydrochloric acid. The deposited crystal was collected by filtration and dissolved in ethanol. The obtained solution was filtered, and then, the filtrate was concentrated under reduced pressure. The obtained residue was crystallized (hexane/ethyl acetate) and further recrystallized (hexane/ethyl acetate) to obtain the title compound (151 mg).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionWater was added to the obtained residue
  3. filtrationThe deposited crystal was collected by filtration
  4. dissolutiondissolved in ethanol
  5. filtrationThe obtained solution was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was crystallized (hexane/ethyl acetate)
  8. customfurther recrystallized (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7b91da7b480a4e46800e9026a96026de
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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