Triethylamine → N-cyclopropyl-1-{4-[(N,N-dimethylglycyl)amino]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxamide

HRID 1717237Notes

Reaction equation

HRID 1717237 reaction equation
[CH2:1]([N:3]([CH2:6]C)[CH2:4]C)[CH3:2].C1C=CC2N([OH:17])N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[C:40]([CH2:41][CH2:42][CH3:43])=[C:39]([C:44]([NH:46][CH:47]3[CH2:49][CH2:48]3)=[O:45])[N:38]=[N:37]2)=[CH:32][CH:31]=1>ClCCl.Cl.CN(C)CC(O)=O>[CH:47]1([NH:46][C:44]([C:39]2[N:38]=[N:37][N:36]([C:33]3[CH:34]=[CH:35][C:30]([NH:29][C:2](=[O:17])[CH2:1][N:3]([CH3:6])[CH3:4])=[CH:31][CH:32]=3)[C:40]=2[CH2:41][CH2:42][CH3:43])=[O:45])[CH2:48][CH2:49]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 685175481-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 68511935N-cyclopropyl-1-{4-[(N,N-dimethylglycyl)amino]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxamideYield 24%

Reagents, catalysts & solvents 2

HCID 75605N,N-Dimethylglycine hydrochlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dimethylglycine hydrochloride (0.17 mg), triethylamine (0.17 ml) and HOBt (0.18 g) in dichloromethane (10 ml) was added WSC (0.23 g), and the mixture was stirred at room temperature for 20 min. 1-(4-Aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide (0.29 g) obtained in Example 1d) was added to the reaction mixture, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with dichloromethane, and washed with aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by high performance liquid chromatography to give the title compound as a white powder (0.09 g, 24%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. washwashed with aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-5631716c378e46b39f480bfad479c940
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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