Sodium Hydroxide → HCID 117992090, compound

HRID 531138Notes

Reaction equation

HRID 531138 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][CH3:21])=[C:8]([CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([N:29]4[CH2:38][CH2:37][C:36]5[N:35]=[C:34]([CH2:39][CH2:40][CH3:41])[C:33]([C:42]([O:44]C)=[O:43])=[CH:32][C:31]=5[C:30]4=[O:46])[CH2:25][CH2:24]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][CH3:21])=[C:8]([CH2:22][N:23]3[CH2:24][CH2:25][CH:26]([N:29]4[CH2:38][CH2:37][C:36]5[N:35]=[C:34]([CH2:39][CH2:40][CH3:41])[C:33]([C:42]([OH:44])=[O:43])=[CH:32][C:31]=5[C:30]4=[O:46])[CH2:27][CH2:28]3)[CH:7]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117992123HCID 117992123, compound

Product 1

HCID 117992090HCID 117992090, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 2 M aqueous sodium hydroxide solution (2 mL) was added at room temperature to an ethanol (8 mL) solution of methyl 6-(1-((6-cyclopropyl-2,4′-difluoro-3-methoxybiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (335 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 crystals were collected by filtration and dissolved in ethanol, 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 (276 mg).

Workup

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

Sources & evidence

ORD record
ord-b7142e3e706e4f1fb4c9c5d50f35e62e
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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