Benzylamine → HCID 68514274, compound

HRID 1717242Notes

Reaction equation

HRID 1717242 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([CH2:25][CH2:26][CH3:27])=[C:23]([C:28]([NH:30][CH:31]3[CH2:33][CH2:32]3)=[O:29])[N:22]=[N:21]2)=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C.[CH2:43]([NH2:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>ClCCl.C(OCC)(=O)C>[CH2:43]([NH:50][C:5]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([CH2:25][CH2:26][CH3:27])=[C:23]([C:28]([NH:30][CH:31]3[CH2:32][CH2:33]3)=[O:29])[N:22]=[N:21]2)=[CH:16][CH:15]=1)=[O:11])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 685175481-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 68514274HCID 68514274, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of triphosgene (0.08 g) in dichloromethane (7 ml) was added dropwise a solution of 1-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide (0.21 g) obtained in Example 1d) and N,N-diisopropylethylamine (0.13 ml) in dichloromethane (3 ml) under ice-cooling, and the mixture was stirred under ice-cooling for 30 min. A solution of benzylamine (0.12 ml) and N,N-diisopropylethylamine (0.13 ml) in dichloromethane (3 ml) was added. The mixture was stirred at room temperature for 20 hr and diluted with ethyl acetate. The ethyl acetate solution was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate). The resultant product was recrystallized from diethyl ether/methanol to give the title compound as a colorless powder (0.16 g, 52%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 min
  3. stirringThe mixture was stirred at room temperature for 20 hr
  4. washThe ethyl acetate solution was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate)
  8. customThe resultant product was recrystallized from diethyl ether/methanol

Sources & evidence

ORD record
ord-9318ead5d7964029a8b15862c4cfba3c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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