Ethoxyethylamine → N1-Ethyl-5-(2-(((2-ethoxyethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide

HRID 2215508Notes

Reaction equation

HRID 2215508 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23](=[O:31])OC4C=CC=CC=4)[CH:17]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[O:5])[CH3:2].[CH2:32]([O:34][CH2:35][CH2:36][NH2:37])[CH3:33]>CN(C)C=O>[CH2:1]([NH:3][C:4]([N:6]1[C:14]2[C:13](=[CH:12][C:11]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]([NH:37][CH2:36][CH2:35][O:34][CH2:32][CH3:33])=[O:31])[CH:17]=3)=[CH:10][CH:9]=2)[CH:8]=[CH:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 66970EthoxyethylamineHCID 21949099Phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate

Product 1

HCID 10454295N1-Ethyl-5-(2-(((2-ethoxyethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate (100 mg, 0.24 mmol) was dissolved in N,N-dimethylformamide (1.0 ml), and 2-ethoxyethylamine (0.063 ml, 0.6 mmol) was added while stirred at room temperature. After 1 hour, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the crystals were precipitated from ethyl acetate-hexane (1:5), filtered off, and dried under aeration to yield the title compound (100 mg, 0.24 mmol, quantitative) as white crystals.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe crystals were precipitated from ethyl acetate-hexane (1:5)
  6. filtrationfiltered off
  7. customdried under aeration

Sources & evidence

ORD record
ord-37a4786540554f72a277addd115d9462
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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