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Water → 5-((2-Aminopyridin-4-yl)oxy)-6-(2-ethoxyethoxy)-N-methyl-1H-indole-1-carboxamide

HRID 1427041
Notes
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Reaction equation

HRID 1427041 reaction equation
[H-].[Na+].[CH2:3]([O: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)[CH3:4].[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][O:5][CH2:3][CH3:4])[N:15]([C:28]([NH:27][CH3:26])=[O:29])[CH:14]=[CH:13]3)[CH:24]=[CH:23][N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 16034Phenyl MethylcarbamateHCID 24758Sodium hydrideHCID 867303434-((6-(2-Ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine

Product 1

HCID 867303445-((2-Aminopyridin-4-yl)oxy)-6-(2-ethoxyethoxy)-N-methyl-1H-indole-1-carboxamideYield 87%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

50-72% Oily sodium hydride (265 mg) was added to a solution of 4-((6-(2-ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine described in Production Example 24-7 (1.92 g, 6.13 mmol) in N,N-dimethylformamide (20 mL) under nitrogen atmosphere at 0° C. The reaction liquid was stirred at the same temperature for 10 minutes. Phenyl methylcarbamate described in Production Example 1-7 (1.20 g, 7.97 mmol) was added to the reaction liquid, and then the mixture was warmed to mom temperature and stirred for 1 hour. 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 (the solution: n-heptane:ethyl acetate=9:1-0:1) to obtain the title compound (1.97 g, 87%).

Workup

  1. customThe reaction liquid
  2. additionwas added to the reaction liquid
  3. temperaturethe mixture was warmed to mom temperature
  4. stirringstirred for 1 hour
  5. washThe organic layer was washed serially with water
  6. dry with materiala saturated saline solution and then dried over anhydrous sodium sulfate
  7. customThe drying agent was separated by filtration
  8. concentrationthe filtrate was concentrated under vacuum
  9. customThe residue was purified with NH silica gel column chromatography (the solution

Sources & evidence

ORD record
ord-13227ae2ace641cb9464aabe13280709
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933099B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes