Hydrochloric Acid → HCID 118037667, compound

HRID 2272496Notes

Reaction equation

HRID 2272496 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[C:19]([CH2:27][CH3:28])[C:18]4=[O:29])[CH2:13][CH2:12]3)[C:7]([O:30][CH:31]([CH3:33])[CH3:32])=[CH:6][C:5]=2[C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=2[F:41])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([CH2:27][CH3:28])[C:18]4=[O:29])[CH2:13][CH2:12]3)[C:7]([O:30][CH:31]([CH3:33])[CH3:32])=[CH:6][C:5]=2[C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=2[F:41])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118037859HCID 118037859, compound

Product 1

HCID 118037667HCID 118037667, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 1-(1-((2-cyclopropyl-2′,4′-difluoro-5-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-ethyl-2-oxo-1,2-dihydropyridine-4-carboxylate (208 mg), a 1 M aqueous sodium hydroxide solution (3 mL), and ethanol (6 mL) was stirred at 70 C for 1 hour. The reaction mixture was pH-adjusted to 3 using 1 M hydrochloric acid, followed by extraction with ethyl acetate twice. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was recrystallized (2-propanol/hexane) to obtain the title compound (156 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was recrystallized (2-propanol/hexane)

Sources & evidence

ORD record
ord-a44d2c4a73d04a44ad35951c42902850
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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