1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57665218, compound

HRID 1717300Notes

Reaction equation

HRID 1717300 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][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:15]([C:26](O)=[O:27])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:32]2N(O)N=[N:35][C:33]=2[CH:34]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.O>[CH:33]1([NH:35][C:26]([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[CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:27])[CH2:34][CH2:32]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68511933HCID 68511933, compound

Product 1

HCID 57665218HCID 57665218, compoundYield 188.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(3-phenylpropyl)-1H-1,2,3-triazole-4-carboxylic acid (398 mg, 1.05 mmol) obtained in Example 100b), HOBt (71.8 mg, 0.526 mmol, 0.5 eq.) and cyclopropylamine (0.098 ml, 1.37 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 6 ml), WSC (247 mg, 1.26 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 12 hr. Water (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 (414 mg, 0.992 mmol, 94.4%).

Workup

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

Sources & evidence

ORD record
ord-054565b612e84f9aa23ac0aa43c574cb
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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