1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(2-methylprop-1-en-1-yl)-1H-1,2,3-triazole-4-carboxamide

HRID 1717290Notes

Reaction equation

HRID 1717290 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH:17]=[C:18]([CH3:20])[CH3:19])=[C:15]([C:21]([OH:23])=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:27]2N(O)N=[N:30][C:28]=2[CH:29]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C>[CH:28]1([NH:30][C:21]([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[CH:17]=[C:18]([CH3:20])[CH3:19])=[O:23])[CH2:29][CH2:27]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68515561HCID 68515561, compound

Product 1

HCID 57664717N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(2-methylprop-1-en-1-yl)-1H-1,2,3-triazole-4-carboxamideYield 191.3%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(2-methylprop-1-en-1-yl)-1H-1,2,3-triazole-4-carboxylic acid (490 mg, 1.56 mmol) obtained in Example 95b), HOBt (106 mg, 0.779 mmol, 0.5 eq.) and cyclopropylamine (0.145 ml, 2.03 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 8.0 ml), WSC (366 mg, 1.87 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate-hexane (5:1, 48 ml) and washed with 2% aqueous sodium carbonate solution, 10% aqueous ammonium chloride solution and saturated brine. The aqueous layers were each extracted with ethyl acetate-hexane-THF (4:1:1, 48 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated, and ethyl acetate was added to the residue. The precipitate was collected by filtration, washed with ethyl acetate and diethyl ether and dried to give the title compound as a white powder (526 mg, 1.49 mmol, 95.4%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate-hexane (5:1, 48 ml)
  3. washwashed with 2% aqueous sodium carbonate solution, 10% aqueous ammonium chloride solution and saturated brine
  4. extractioneach extracted with ethyl acetate-hexane-THF (4:1:1, 48 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additionethyl acetate was added to the residue
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with ethyl acetate and diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-6cb75832581742049f5fbeb846e5c64c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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