1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664834, compound

HRID 1717298Notes

Reaction equation

HRID 1717298 reaction equation
[CH2:1]([C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=2)[N:11]=[N:10][C:9]=1[C:24](O)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[C:30]2N(O)N=[N:33][C:31]=2[CH:32]=1.C1(N)CC1.CCN=C=NCCCN(C)C.C(=O)([O-])O.[Na+]>C(#N)C.CN(C=O)C>[CH2:1]([C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=2)[N:11]=[N:10][C:9]=1[C:24]([NH:33][CH:31]1[CH2:32][CH2:30]1)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 68516755HCID 68516755, compound

Product 1

HCID 57664834HCID 57664834, compoundYield 177%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

5-Benzyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid (354 mg, 1.01 mmol) obtained in Example 99a), HOBt (69.0 mg, 0.505 mmol, 0.5 eq.) and cyclopropylamine (0.094 ml, 1.31 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 6 ml), WSC (217 mg, 1.11 mmol, 1.1 eq.) was added, and the mixture was stirred at room temperature for 3.5 hr. 1% aqueous sodium hydrogen carbonate solution (20 ml) was added to the reaction mixture, and the mixture was stirred. The precipitate was collected by filtration, washed with water and dried to give the title compound as a white powder (348 mg, 0.894 mmol, 88.5%).

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-5945392e1c064ff48b2a32efd83bb9a0
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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