1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664900, compound

HRID 1717311Notes

Reaction equation

HRID 1717311 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([C:25](O)=[O:26])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:31]2N(O)N=[N:34][C:32]=2[CH:33]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.O>[CH:32]1([NH:34][C:25]([C:15]2[N:14]=[N:13][N:12]([C:9]3[CH:10]=[CH:11][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=3)[C:16]=2/[CH:17]=[CH:18]/[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:26])[CH2:33][CH2:31]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68514308HCID 68514308, compound

Product 1

HCID 57664900HCID 57664900, compoundYield 176.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-[(E)-2-phenylvinyl]-1H-1,2,3-triazole-4-carboxylic acid (264 mg, 0.728 mmol) obtained in Example 106b), HOBt (49.7 mg, 0.364 mmol, 0.5 eq.) and cyclopropylamine (0.068 ml, 0.947 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (3:1, 4 ml), WSC (171 mg, 0.874 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 13 hr. Water (10 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 (258 mg, 0.643 mmol, 88.3%).

Workup

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

Sources & evidence

ORD record
ord-b48d00e52db744059085f8c9d7685a4f
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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