Water → HCID 86730360, compound

HRID 1427058Notes

Reaction equation

HRID 1427058 reaction equation
[H-].[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]([NH2:25])[CH:20]=1.[CH3:26][NH:27][C:28](=O)[O:29]C1C=CC=CC=1.O>CN(C)C=O.C(OCC)(=O)C>[NH2:25][C:21]1[CH:20]=[C:19]([O:18][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][C:9]=2[O:8][CH2:7][CH2:6][CH2:5][O:4][CH3:3])[N:15]([C:28]([NH:27][CH3:26])=[O:29])[CH:14]=[CH:13]3)[CH:24]=[CH:23][N:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 16034Phenyl MethylcarbamateHCID 24758Sodium hydrideHCID 86730358HCID 86730358, compound

Product 1

HCID 86730360HCID 86730360, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

50-72% Oily sodium hydride (308 mg) was added to a solution of 4-((6-(3-methoxypropoxy)-1H-indol-5-yl)oxy)pyridin-2-amine described in Production Example 32-7 (2.23 g, 7.12 mmol) in N,N-dimethylformamide (30 mL) under nitrogen atmosphere at 0° C. The reaction liquid was stirred for 10 minutes, then phenyl methylcarbamate described in Production Example 1-7 (1.40 g, 9.25 mmol) was added, and the resultant was further stirred at the same temperature for 30 minutes. Water and ethyl acetate were added to the reaction liquid. The organic layer was washed serially with water and 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 NH silica gel column chromatography (n-heptane:ethyl acetate=9:1-0:1) to obtain the title compound (2.44 g, 93%).

Workup

  1. customThe reaction liquid
  2. additionwas added
  3. stirringthe resultant was further stirred at the same temperature for 30 minutes
  4. washThe organic layer was washed serially with water
  5. dry with materiala saturated saline solution and then dried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe filtrate was concentrated under vacuum
  8. customThe residue was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=9:1-0:1)

Sources & evidence

ORD record
ord-47a0cff85a41475e9ffde641b5b3d71f
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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