N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1-trityl-1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamide → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamide

HRID 1717373Notes

Reaction equation

HRID 1717373 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:38]3[CH:43]=[CH:42][C:41]([C:44]([NH:46][CH2:47][CH3:48])=[O:45])=[CH:40][CH:39]=3)[C:11]=2/[CH:12]=[CH:13]/[C:14]2[N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=[CH:17][N:18]=2)=[O:6])[CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:38]3[CH:39]=[CH:40][C:41]([C:44]([NH:46][CH2:47][CH3:48])=[O:45])=[CH:42][CH:43]=3)[C:11]=2/[CH:12]=[CH:13]/[C:14]2[NH:18][CH:17]=[CH:16][N:15]=2)=[O:6])[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 68513554N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1-trityl-1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 136104428N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamideYield 53.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1-trityl-1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamide (670 mg) obtained in Example 322a) was dissolved in trifluoroacetic acid (5 ml), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in chloroform. This chloroform solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column (ethyl acetate to ethyl acetate/methanol=4/1) to give the title compound as a white powder (220 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in chloroform
  3. washThis chloroform solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column (ethyl acetate to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-300c8e3a9b84462b967510b191af0c1d
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…