Water → HCID 86730358, compound
Reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25]C(=O)C)[CH:20]=1.C(OCC)(=O)C.O>CO>[CH3:3][O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A 2 M sodium hydroxide solution (30 mL) was added to a solution of N-(4-((6-(3-methoxypropoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 32-6 (2.8 g, 7.88 mmol) in methanol (30 mL) under nitrogen atmosphere at room temperature. The liquid mixture was stirred under reflux under a thermal condition of 75° C. for 2 hours. The reaction liquid was allowed to stand to cool to room temperature, and then ethyl acetate and water were added. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:9-0:1-ethyl acetate:methanol=49:1) to obtain the title compound (2.24 g, 91%).
Workup
- customThe reaction liquid
- temperatureto cool to room temperature
- washThe organic layer was washed with a saturated saline solution
- dry with materialdried over anhydrous sodium sulfate
- customThe drying agent was separated by filtration
- concentrationthe filtrate was concentrated under vacuum
- customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:9-0:1-ethyl acetate:methanol=49:1)
Sources & evidence
- ORD record
- ord-e8e4e6843187427cafdc00b9f61a4e10
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933099B2
Reaction notes
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