1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57665087, compound

HRID 1717296Notes

Reaction equation

HRID 1717296 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][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([C:25]([OH:27])=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].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>[CH:32]1([NH:34][C:25]([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][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:27])[CH2:33][CH2:31]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68515292HCID 68515292, compound

Product 1

HCID 57665087HCID 57665087, compoundYield 189.2%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(2-phenylethyl)-1H-1,2,3-triazole-4-carboxylic acid (501 mg, 1.37 mmol) obtained in Example 98b), HOBt (93.8 mg, 0.687 mmol, 0.5 eq.) and cyclopropylamine (0.128 ml, 1.79 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 7.5 ml), WSC (323 mg, 1.65 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate (40 ml) and washed with 2% aqueous sodium carbonate solution (×2), 10% aqueous ammonium chloride solution and saturated brine. The aqueous layer was each extracted with ethyl acetate-hexane (2:1, 30 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (526 mg, 1.30 mmol, 95.2%).

Workup

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

Sources & evidence

ORD record
ord-07e01d71f9614e7a8b11323ba1b08782
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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