1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68516394, compound

HRID 1717259Notes

Reaction equation

HRID 1717259 reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([C:22]([OH:24])=O)[N:16]=[N:15]2)=[CH:10][CH:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].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>[CH2:1]([NH:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([C:22]([NH:31][CH:29]3[CH2:30][CH2:28]3)=[O:24])[N:16]=[N:15]2)=[CH:12][CH:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68512088HCID 68512088, compound

Product 1

HCID 68516394HCID 68516394, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

1-{4-[(Butylamino)carbonyl]phenyl}-5-propyl-1H-1,2,3-triazole-4-carboxylic acid (504 mg, 1.53 mmol) obtained in Example 56b), HOBt (208 mg, 1.53 mmol, 1.0 eq.) and cyclopropylamine (0.142 ml, 1.98 mmol, 1.3 eq.) were dissolved in acetonitrile (4 ml) and DMF (4 ml), WSC (358 mg, 1.83 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was concentrated, dissolved in ethyl acetate (50 ml), and washed with 5% aqueous sodium hydrogen carbonate solution, 10% aqueous ammonium chloride solution and saturated brine. The aqueous layers were each extracted with ethyl acetate-hexane (2:1, 20 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and 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 (535 mg, 1.45 mmol, 94.9%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (50 ml)
  3. washwashed with 5% aqueous sodium hydrogen carbonate solution, 10% aqueous ammonium chloride solution and saturated brine
  4. extractioneach extracted with ethyl acetate-hexane (2:1, 20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additiondiethyl ether was added
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-97c2b847c96148b3ad50098e38a89700
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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