Water → HCID 70874027, compound

HRID 2208932Notes

Reaction equation

HRID 2208932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:22]([CH2:33][CH3:34])[CH:23]2[CH2:32][CH2:31][C:26]3(OCC[O:27]3)[CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8].O.CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:22]([CH2:33][CH3:34])[CH:23]2[CH2:24][CH2:25][C:26](=[O:27])[CH2:31][CH2:32]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 70874590HCID 70874590, compound

Product 1

HCID 70874027HCID 70874027, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 5-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(1,4-dioxaspiro[4.5]decan-8-yl)amino)-2-methylbenzamide (2.0 g, 4.1 mmol) in acetone: water (14 mL+6 mL) was added PTSA (3.1 g, 16 mmol). The resulting reaction mixture was stirred at 70° C. overnight. On completion, the solvent was removed under reduced pressure and the residue was basified with aqueous sodium bicarbonate. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with water, dried, concentrated under reduced pressure to give the title compound (1.5 g, 83%) which was used directly in the next step.

Workup

  1. customThe resulting reaction mixture
  2. customOn completion, the solvent was removed under reduced pressure
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3eda47bc0f354b0a92bce844eade742d
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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