1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664898, compound

HRID 1717307Notes

Reaction equation

HRID 1717307 reaction equation
[Cl:1][CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)[N:6]=[N:5][C:4]=1[C:19]([OH:21])=O.C1C=C[C:25]2N(O)N=[N:28][C:26]=2[CH:27]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.O>[Cl:1][CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:13]=2)[N:6]=[N:5][C:4]=1[C:19]([NH:28][CH:26]1[CH2:27][CH2:25]1)=[O:21]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68512668HCID 68512668, compound

Product 1

HCID 57664898HCID 57664898, compoundYield 131.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

5-(Chloromethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid (103 mg, 0.334 mmol) obtained in Example 104b), HOBt (23 mg, 0.167 mmol, 0.5 eq.) and cyclopropylamine (0.031 ml, 0.434 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 1.5 ml), WSC (78.4 mg, 0.401 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2.5 hr. water (10 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (30 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution, washed with 10% aqueous ammonium chloride solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated to give a white powder. This was subjected to column chromatography (elution solvent, ethyl acetate-hexane=2:3-3:2) on silica gel (manufactured by E. Merck, Art.7734, 10 g). The fraction obtained by elution with ethyl acetate-hexane (1:1-3:2) was 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 (76 mg, 0.219 mmol, 65.4%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (30 ml)
  2. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution
  3. washwashed with 10% aqueous ammonium chloride solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give a white powder
  7. washThis was subjected to column chromatography (elution solvent, ethyl acetate-hexane=2:3-3:2) on silica gel (manufactured by E. Merck, Art.7734, 10 g)
  8. customThe fraction obtained by elution with ethyl acetate-hexane (1:1-3:2)
  9. concentrationwas concentrated
  10. additiondiethyl ether was added to the residue
  11. filtrationThe precipitate was collected by filtration
  12. washwashed with diethyl ether
  13. customdried

Sources & evidence

ORD record
ord-a7fd902b53a441679180472bffa33ca6
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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