1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68516290, compound

HRID 1717229Notes

Reaction equation

HRID 1717229 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH2:15][CH2:16][CH3:17])=[C:13]([C:18]([OH:20])=O)[N:12]=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:21]1([NH2:24])[CH2:23][CH2:22]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(#N)C>[CH:21]1([NH:24][C:18]([C:13]2[N:12]=[N:11][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[C:14]=2[CH2:15][CH2:16][CH3:17])=[O:20])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 433810581-(4-nitrophenyl)-5-propyl-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 68516290HCID 68516290, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-nitrophenyl)-5-propyl-1H-1,2,3-triazole-4-carboxylic acid (1.38 g) obtained in Example 1b) in acetonitrile (50 ml) were successively added cyclopropylamine (0.38 ml), HOBt (0.84 g) and WSC (1.05 g), and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate 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 silica gel column (ethyl acetate/hexane=1/1) to give the title compound as a pale-yellow solid (1.29 g, 82%).

Workup

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

Sources & evidence

ORD record
ord-8fb3a997258e419b890d8cc877dd3e65
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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