Sodium Hydroxide → HCID 117992573, compound

HRID 531072Notes

Reaction equation

HRID 531072 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][C:13]=3[F:19])=[C:10]([F:20])[C:9]([O: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]C)=[O:44])=[CH:33][C:32]=5[C:31]4=[O:47])[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][C:13]=3[F:19])=[C:10]([F:20])[C:9]([O: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:47])[CH2:28][CH2:29]3)[CH:7]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117992165HCID 117992165, compound

Product 1

HCID 117992573HCID 117992573, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 2 M aqueous sodium hydroxide solution (1.5 mL) was added at room temperature to an ethanol (8 mL) solution of methyl 6-(1-((6-cyclopropyl-2,2′,4′-trifluoro-3-methoxybiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (244 mg), and the mixture was stirred at 80° C. for 2 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, followed by extraction with a mixed solution of ethyl acetate and THF. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was crystallized (hexane/ethyl acetate) and further recrystallized (hexane/ethanol) to obtain the title compound (160 mg).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionWater was added to the obtained residue
  3. extractionfollowed by extraction with a mixed solution of ethyl acetate and THF
  4. washThe obtained organic layer was washed with water and saturated saline in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was crystallized (hexane/ethyl acetate)
  8. customfurther recrystallized (hexane/ethanol)

Sources & evidence

ORD record
ord-c5f798b5fb9c4810b2ce0ca64ba6392c
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

Loading…