Hydrochloric Acid → HCID 118037518, compound

HRID 2272503Notes

Reaction equation

HRID 2272503 reaction equation
[CH:1]1([C:4]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:8]([F:18])[C:7]([O:19][CH:20]([CH3:22])[CH3:21])=[C:6]([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]([CH2:40][CH3:41])[C:31]4=[O:42])[CH2:26][CH2:25]3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([C:4]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:8]([F:18])[C:7]([O:19][CH:20]([CH3:22])[CH3:21])=[C:6]([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]([CH2:40][CH3:41])[C:31]4=[O:42])[CH2:28][CH2:29]3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118037630HCID 118037630, compound

Product 1

HCID 118037518HCID 118037518, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 1-(1-((6-cyclopropyl-2,2′,4′-trifluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-ethyl-2-oxo-1,2-dihydropyridine-4-carboxylate (161 mg), a 1 M aqueous sodium hydroxide solution (1 mL), and ethanol (2 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 organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was crystallized (2-propanol/hexane) to obtain the title compound (123 mg).

Workup

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

Sources & evidence

ORD record
ord-7785711f410b426c942d235611472979
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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