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

HRID 1717376Notes

Reaction equation

HRID 1717376 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=3)[C:11]=2/[CH:12]=[CH:13]/[C:14]2[NH:15][CH:16]=[CH:17][N:18]=2)=[O:6])[CH2:3][CH2:2]1.CI.[C:32](=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:24]=3)[C:11]=2/[CH:12]=[CH:13]/[C:14]2[N:18]([CH3:32])[CH:17]=[CH:16][N:15]=2)=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136104428N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 57664826N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1-methyl-1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamideYield 12.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(E)-2-(1H-imidazol-2-yl)vinyl]-1H-1,2,3-triazole-4-carboxamide (150 mg) obtained in Example 322 was dissolved in acetone (3 ml) and DMF (3 ml), methyl iodide (72 μl) and potassium carbonate (300 mg) were added, and the mixture was stirred at room temperature for 3 days. After an insoluble material was removed by filtration, the reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in chloroform. The obtained chloroform solution was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate-methanol (10:1) to give the title compound as a white powder (20 mg).

Workup

  1. customAfter an insoluble material was removed by filtration
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe obtained residue was dissolved in chloroform
  4. washThe obtained chloroform solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was recrystallized from ethyl acetate-methanol (10:1)

Sources & evidence

ORD record
ord-571ca96436c741f9a2cf0bb3fd36d030
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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