1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86629799, compound

HRID 1717269Notes

Reaction equation

HRID 1717269 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.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]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:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 30341844-Azidobenzoic acid

Product 1

HCID 86629799HCID 86629799, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

4-Azidobenzoic acid (846 mg, 5.08 mmol), HOBt (416 mg, 3.05 mmol, 0.6 eq.) and N-(2-aminoethyl)morpholine (0.716 ml, 5.34 mmol, 1.05 eq.) were dissolved in acetonitrile (9 ml) and DMF (3 ml), WSC (1.19 g, 6.10 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, dissolved in ethyl acetate (40 ml), and washed with 5% aqueous sodium carbonate solution and saturated brine. The aqueous layers were each extracted with ethyl acetate (30 ml). The organic layers were combined, 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 (40 ml)
  3. washwashed with 5% aqueous sodium carbonate solution and saturated brine
  4. extractioneach extracted with ethyl acetate (30 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at 30° C. or below

Sources & evidence

ORD record
ord-11dffe7c16f44098adb40cfd85fa6344
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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