1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57665205, compound

HRID 1717302Notes

Reaction equation

HRID 1717302 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][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:15]([C:28](O)=[O:29])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:34]2N(O)N=[N:37][C:35]=2[CH:36]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.O>[CH:35]1([NH:37][C:28]([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][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:29])[CH2:36][CH2:34]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68514388HCID 68514388, compound

Product 1

HCID 57665205HCID 57665205, compoundYield 191.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(5-phenylpentyl)-1H-1,2,3-triazole-4-carboxylic acid (392 mg, 0.964 mmol) obtained in Example 101b), HOBt (67.3 mg, 0.482 mmol, 0.5 eq.) and cyclopropylamine (0.090 ml, 1.25 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 6 ml), WSC (226 mg, 1.16 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 13.5 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 methanol-water (1:1) and dried to give the title compound as a white powder (412 mg, 0.925 mmol, 95.9%).

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and methanol-water (1:1)
  4. customdried

Sources & evidence

ORD record
ord-8a680bd3298148a1a7ea3e5a5d88c86e
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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