1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxamide

HRID 1717251Notes

Reaction equation

HRID 1717251 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]([C:20]([OH:22])=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH:23]1([NH2:26])[CH2:25][CH2:24]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.C(N(CC)CC)C>[CH:23]1([NH:26][C:20]([C:15]2[N:14]=[N:13][N:12]([C:9]3[CH:8]=[CH:7][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=3)[C:16]=2[CH2:17][CH2:18][CH3:19])=[O:22])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 685176031-[4-[(ethylamino)carbonyl]phenyl]-5-propyl-1H-1,2,3-Triazole-4-carboxylic acid

Product 1

HCID 16222143N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxamideYield 44%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a solution of 1-{4-[(ethylamino)carbonyl]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxylic acid (0.40 g) obtained in Example 43b) in acetonitrile-DMF (7:2, 9 ml) were successively added cyclopropylamine (0.11 ml), triethylamine (0.22 ml), HOBt (0.24 g) and WSC (0.30 g), and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) to give the title compound as a white powder (0.20 g, 44%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-4e45f65af48344cba5c5682b03af602a
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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