1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664965, compound

HRID 1717312Notes

Reaction equation

HRID 1717312 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)[N:14]=[N:13][C:12]=1[C:27](O)=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[C:33]2N(O)N=[N:36][C:34]=2[CH:35]=1.C1(N)CC1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)[N:14]=[N:13][C:12]=1[C:27]([NH:36][CH:34]1[CH2:35][CH2:33]1)=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 685149955-[2-(Benzyloxy)ethyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 57664965HCID 57664965, compoundYield 127.2%

Reagents, catalysts & solvents 2

HCID 21226206Ethyl acetate hexaneSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

5-[2-(Benzyloxy)ethyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid (375 mg, 0.951 mmol) obtained in Example 107b), HOBt (64.9 mg, 0.475 mmol, 0.5 eq.) and cyclopropylamine (0.088 ml, 1.24 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 4.5 ml), WSC (223 mg, 1.14 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate-hexane (4:1, 50 ml), washed twice with 2% aqueous sodium carbonate solution and with 10% aqueous sodium chloride solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:2-3:2) 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. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (262 mg, 0.604 mmol, 79.4%).

Workup

  1. washwashed twice with 2% aqueous sodium carbonate solution and with 10% aqueous sodium chloride solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. washThe residue was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:2-3:2) on silica gel (manufactured by E. Merck, Art.7734, 10 g)
  5. customThe fraction obtained by elution with ethyl acetate-hexane (1:1-3:2)
  6. concentrationwas concentrated
  7. additiondiethyl ether was added
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-09cbdc37ae1243cea4260b2ae69352d4
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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