1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664798, compound

HRID 1717306Notes

Reaction equation

HRID 1717306 reaction equation
[CH:1]1([CH2:6][C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=3)[N:10]=[N:9][C:8]=2[C:23]([OH:25])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.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:1]1([CH2:6][C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=3)[N:10]=[N:9][C:8]=2[C:23]([NH:32][CH:30]2[CH2:31][CH2:29]2)=[O:25])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68511336HCID 68511336, compound

Product 1

HCID 57664798HCID 57664798, compoundYield 200.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

5-(Cyclopentylmethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid (359 mg, 1.05 mmol) obtained in Example 103b), HOBt (71.6 mg, 0.524 mmol, 0.5 eq.) and cyclopropylamine (0.097 ml, 1.36 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 4.5 ml), WSC (246 mg, 1.26 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 14 hr. Water (15 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 (400 mg, 1.05 mmol, quant.).

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-167f3cc263fa438b8779a382859a54f9
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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