Propylamine → HCID 86629794, compound

HRID 1717254Notes

Reaction equation

HRID 1717254 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=[CH:15][C:16]2N(O)N=[N:19][C:17]=2C=1.C(N)CC.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:19][CH2:17][CH2:16][CH3:15])=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 7852PropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 30341844-Azidobenzoic acid

Product 1

HCID 86629794HCID 86629794, compoundYield 188.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

4-Azidobenzoic acid (866 mg, 5.20 mmol), HOBt (710 mg, 5.20 mmol, 1.0 eq.) and n-propylamine (0.568 ml, 7.60 mmol, 1.3 eq.) were dissolved in acetonitrile (6 ml) and DMF (6 ml), WSC (1.22 g, 6.24 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 4 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 (2.0 g, including residual solvent).

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-65846291e5254ddf9c20cc56bf942918
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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