Dimethylcarbamoyl Chloride → HCID 68514350, compound

HRID 1717243Notes

Reaction equation

HRID 1717243 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])[N:10]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:29][N:30]([CH3:34])[C:31](Cl)=[O:32]>ClCCl.CN(C)C1C=CN=CC=1>[CH:19]1([NH:18][C:16]([C:11]2[N:10]=[N:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:31]([N:30]([CH3:34])[CH3:29])=[O:32])=[CH:3][CH:4]=3)[C:12]=2[CH2:13][CH2:14][CH3:15])=[O:17])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 685175481-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 68514350HCID 68514350, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide (0.32 g) obtained in Example 1d) and triethylamine (1.5 ml) in dichloromethane (7 ml) was added dimethylcarbamoyl chloride (0.15 g) under ice-cooling. The mixture was stirred at room temperature for 4 hr, N,N-dimethylpyridin-4-amine (0.14 g) was added, and the mixture was further stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with 1N hydrochloric acid and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column (hexane/ethyl acetate=7/3 to ethyl acetate), and the resultant product was recrystallized from ethanol to give the title compound as a colorless powder (0.26 g, 64%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred at room temperature for 15 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with 1N hydrochloric acid and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column (hexane/ethyl acetate=7/3 to ethyl acetate)
  9. customthe resultant product was recrystallized from ethanol

Sources & evidence

ORD record
ord-27b22668650c4e91ae0224771663b748
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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