1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86629798, compound

HRID 1717266Notes

Reaction equation

HRID 1717266 reaction equation
[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].C1C=CC2N(O)N=NC=2C=1.[C:23]1([CH2:29][CH2:30][CH2:31][NH2:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C>C(#N)C.CN(C=O)C>[N:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:32][CH2:31][CH2:30][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 162593-PhenylpropylamineHCID 757711-HydroxybenzotriazoleHCID 30341844-Azidobenzoic acid

Product 1

HCID 86629798HCID 86629798, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

4-Azidobenzoic acid (855 mg, 5.14 mmol), HOBt (701 mg, 5.14 mmol, 1.0 eq.) and 3-phenylpropylamine (0.969 ml, 6.68 mmol, 1.3 eq.) were dissolved in acetonitrile (6 ml) and DMF (6 ml), WSC (1.21 g, 6.16 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated, dissolved in ethyl acetate (50 ml), washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated at 30° C. or below to give the title compound as a pale-yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (50 ml)
  3. washwashed with 5% aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at 30° C. or below

Sources & evidence

ORD record
ord-870088af4df642db91ca87fa474581bd
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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