1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664840, compound

HRID 1717309Notes

Reaction equation

HRID 1717309 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:15]([C:23]([OH:25])=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:29]2N(O)N=[N:32][C:30]=2[CH:31]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.O>[CH:30]1([NH:32][C:23]([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[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:25])[CH2:31][CH2:29]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68514467HCID 68514467, compound

Product 1

HCID 57664840HCID 57664840, compoundYield 174.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid (203 mg, 0.604 mmol) obtained in Example 105a), HOBt (41.2 mg, 0.302 mmol, 0.5 eq.) and cyclopropylamine (0.056 ml, 0.785 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 3.0 ml), WSC (142 mg, 0.724 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 14 hr. Water (5 ml) was added to the reaction mixture and the mixture was stirred at 0° C. The precipitate was collected by filtration, washed with water and dried to give the title compound as a white powder (198 mg, 0.527 mmol, 87.3%).

Workup

  1. stirringthe mixture was stirred at 0° C
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ee30214c958a45ef97ec6b60643da637
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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