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

HRID 1717294Notes

Reaction equation

HRID 1717294 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][CH:19]([CH3:21])[CH3:20])=[C:15]([C:22]([OH:24])=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1C=C[C:28]2N(O)N=[N:31][C:29]=2[CH:30]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C>[CH:29]1([NH:31][C:22]([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][CH:19]([CH3:21])[CH3:20])=[O:24])[CH2:30][CH2:28]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 685149931-{4-[(ethylamino)carbonyl]phenyl}-5-(3-methylbutyl)-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 57665013N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-methylbutyl)-1H-1,2,3-triazole-4-carboxamideYield 185.7%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

1-{4-[(Ethylamino)carbonyl]phenyl}-5-(3-methylbutyl)-1H-1,2,3-triazole-4-carboxylic acid (462 mg, 1.40 mmol) obtained in Example 97b), HOBt (95.4 mg, 0.700 mmol, 0.5 eq.) and cyclopropylamine (0.130 ml, 1.82 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 7.5 ml), WSC (328 mg, 1.68 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 (40 ml) and washed with 2% aqueous sodium carbonate solution (×2), 10% aqueous ammonium chloride solution and saturated brine. The aqueous layers were 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 grayish white powder (481 mg, 1.30 mmol, 93.0%).

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-7228865318f8484a9878b3411dc5bf9e
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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