2-Methoxyethylamine → 1-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-N-(2-methoxyethyl)-1H-1,2,3-triazole-4-carboxamide

HRID 1717345Notes

Reaction equation

HRID 1717345 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17](O)=[O:18])[N:14]=[N:13]2)=[C:8]([O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=1)=[O:5])[CH3:2].[CH3:30][O:31][CH2:32][CH2:33][NH2:34].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O.C(N(CC)CC)C>[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]([NH:34][CH2:33][CH2:32][O:31][CH3:30])=[O:18])[N:14]=[N:13]2)=[C:8]([O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 80182-MethoxyethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 685163141-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 576651101-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-N-(2-methoxyethyl)-1H-1,2,3-triazole-4-carboxamideYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylic acid (0.14 g) obtained in Example 133e) in DMF (4 ml) were successively added 2-methoxyethylamine (0.04 ml), triethylamine (0.06 ml), HOBt (0.07 g) and WSC (0.08 g), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and the deposited precipitate was collected by filtration, washed with water, and recrystallized from ethanol-water to give the title compound as a white powder (0.14 g, 86%).

Workup

  1. filtrationthe deposited precipitate was collected by filtration
  2. washwashed with water
  3. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-ecb38c84196e4d95b807e6b838ec81c4
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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