Sodium Hydroxide → HCID 117992344, compound

HRID 531081Notes

Reaction equation

HRID 531081 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH2:28][CH2:27][C:26]4[N:25]=[C:24]([CH2:29][CH3:30])[C:23]([C:31]([O:33]C)=[O:32])=[CH:22][C:21]=4[C:20]3=[O:35])[CH2:15][CH2:14]2)[CH:7]=[C:6]([CH:36]2[CH2:38][CH2:37]2)[C:5]=1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=1[F:46]>C(O)C>[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([N:19]3[CH2:28][CH2:27][C:26]4[N:25]=[C:24]([CH2:29][CH3:30])[C:23]([C:31]([OH:33])=[O:32])=[CH:22][C:21]=4[C:20]3=[O:35])[CH2:17][CH2:18]2)[CH:7]=[C:6]([CH:36]2[CH2:37][CH2:38]2)[C:5]=1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=1[F:46]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117992222HCID 117992222, compound

Product 1

HCID 117992344HCID 117992344, compoundYield 81.9%

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-((2-chloro-6-cyclopropyl-2′,4′-difluoro-3-methoxybiphenyl-4-yl)methyl)piperidin-4-yl)-2-ethyl-5-oxo-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (301 mg), and the mixture was stirred at 80° C. for 1 hour 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. Then, the deposited crystals were collected by filtration and dissolved in ethanol, and 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 (241 mg).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionWater was added to the obtained residue
  3. filtrationThen, the 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-178ae59083d046498ddb6b31d0c1ee97
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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