Pentylamine → HCID 86629795, compound

HRID 1717260Notes

Reaction equation

HRID 1717260 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].[CH:13]1[CH:14]=[CH:15][C:16]2N(O)N=[N:19][C:17]=2C=1.C(N)CCCC.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][CH2:15][CH2:14][CH3:13])=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 8060PentylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 30341844-Azidobenzoic acid

Product 1

HCID 86629795HCID 86629795, compoundYield 127.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

4-Azidobenzoic acid (846 mg, 5.08 mmol), HOBt (694 mg, 5.08 mmol, 1.0 eq.) and n-pentylamine (0.783 ml, 6.61 mmol, 1.3 eq.) were dissolved in acetonitrile (6 ml) and DMF (6 ml), WSC (1.19 g, 6.10 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 (1.5 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-bed691e6909b4b0f8aab02ceb537756c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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