Ammonia → HCID 68514969, compound

HRID 1717244Notes

Reaction equation

HRID 1717244 reaction equation
ClC(OC1C=C[C:8]([N+:11]([O-])=O)=CC=1)=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]([CH2:26][CH2:27][CH3:28])=[C:24]([C:29]([NH:31][CH:32]3[CH2:34][CH2:33]3)=[O:30])[N:23]=[N:22]2)=[CH:17][CH:16]=1.N.C(OCC)(=[O:38])C>ClCCl.CN(C)C1C=CN=CC=1.CO>[NH2:11][C:8]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]([CH2:26][CH2:27][CH3:28])=[C:24]([C:29]([NH:31][CH:32]3[CH2:33][CH2:34]3)=[O:30])[N:23]=[N:22]2)=[CH:17][CH:16]=1)=[O:38]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 821294-Nitrophenyl chloroformateHCID 685175481-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 68514969HCID 68514969, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-nitrophenyl chloroformate (1.06 g) in dichloromethane (15 ml) was added dropwise a solution of 1-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide (1.0 g) obtained in Example 1d) and N,N-dimethylpyridin-4-amine (0.65 g) in dichloromethane (15 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 7 hr, a solution (2M, 18 ml) of ammonia in methanol was added, and the mixture was further stirred for 10 hr. Ethyl acetate was added to the reaction mixture, and the resulting insoluble material was collected by filtration and recrystallized from methanol/ethyl acetate to give the title compound as a colorless powder (0.91 g, 80%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 10 hr
  3. filtrationthe resulting insoluble material was collected by filtration
  4. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-93e29f0791c340e1810707cac4daf89a
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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