Water → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-[(5-fluoropentyl)oxy]phenyl}-1H-1,2,3-triazole-4-carboxamide

HRID 1717346Notes

Reaction equation

HRID 1717346 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]=3[OH:23])[CH:11]=2)=[O:6])[CH2:3][CH2:2]1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][F:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]=3[O:23][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][F:30])[CH:11]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 120236Pentane, 1-bromo-5-fluoro-HCID 576650001-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-N-cyclopropyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 68514362N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-[(5-fluoropentyl)oxy]phenyl}-1H-1,2,3-triazole-4-carboxamideYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-1H-1,2,3-triazole-4-carboxamide (0.16 g) obtained in Example 139 in DMF (5 ml) were added 1-bromo-5-fluoropentane (0.11 g) and potassium carbonate (0.07 g), and the mixture was stirred at 50° C. overnight. The reaction mixture was allowed to cool to room temperature, and water was added to the reaction mixture. The deposited precipitate was collected by filtration, washed with water, and recrystallized from ethanol-water to give the title compound as a pale-brown powder (0.12 g, 60%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe deposited precipitate was collected by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-e3110286c7434f639cb7196e4b990d4c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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