1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68516769, compound

HRID 1717264Notes

Reaction equation

HRID 1717264 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]([CH2:22][CH2:23][CH3:24])=[C:20]([C:25]([OH:27])=O)[N:19]=[N:18]2)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.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>[CH2:1]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]([CH2:22][CH2:23][CH3:24])=[C:20]([C:25]([NH:34][CH:32]3[CH2:33][CH2:31]3)=[O:27])[N:19]=[N:18]2)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68513197HCID 68513197, compound

Product 1

HCID 68516769HCID 68516769, compoundYield 185.3%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Benzylamino)carbonyl]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxylic acid (507 mg, 1.39 mmol) obtained in Example 58b), HOBt (95 mg, 0.696 mmol, 0.5 eq.) and cyclopropylamine (0.129 ml, 1.81 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 9.0 ml), WSC (327 mg, 1.67 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, dissolved in ethyl acetate (40 ml), and washed with 5% aqueous sodium hydrogen carbonate solution, 10% aqueous ammonium chloride solution and saturated brine. The aqueous layers were each extracted with ethyl acetate-hexane (1:1, 30 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated, and diethyl ether was added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (520 mg, 1.29 mmol, 92.7%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (40 ml)
  3. washwashed with 5% aqueous sodium hydrogen carbonate solution, 10% aqueous ammonium chloride solution and saturated brine
  4. extractioneach extracted with ethyl acetate-hexane (1:1, 30 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additiondiethyl ether was added
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-354c824c867544e1a738529dc26b9e83
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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