4-Bromophenol → 5-[(4-bromophenoxy)methyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

HRID 1717320Notes

Reaction equation

HRID 1717320 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)[C:11]=2[CH2:12][OH:13])=[O:6])[CH2:3][CH2:2]1.[Br:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1.C1(C)C=CC=CC=1>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([O:13][CH2:12][C:11]2[N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)[N:9]=[N:8][C:7]=2[C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:6])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 78084-BromophenolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57665224N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 576650215-[(4-bromophenoxy)methyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamideYield 95.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide (0.10 g) obtained in Example 112 in THF (3 ml)—toluene (3 ml) were added 4-bromophenol (0.053 g), tributylphosphine (0.15 ml) and ADDP (0.15 g). The reaction mixture was stirred at room temperature for 15 min, the insoluble material was filtered off, and the solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=1/2 to ethyl acetate). The resultant product was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (0.14 g, 95%).

Workup

  1. filtrationthe insoluble material was filtered off
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column (hexane/ethyl acetate=1/2 to ethyl acetate)
  4. customThe resultant product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-067dc33a8e6a4536a73bdd7ed05444ce
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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