Butylamine → HCID 49787045, compound

HRID 1717257Notes

Reaction equation

HRID 1717257 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].C1[CH:14]=[CH:15][C:16]2N(O)N=[N:19][C:17]=2C=1.C(N)CCC.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][CH3:14])=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 8007ButylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 30341844-Azidobenzoic acid

Product 1

HCID 49787045HCID 49787045, compoundYield 208.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

4-Azidobenzoic acid (843 mg, 5.06 mmol), HOBt (691 mg, 5.06 mmol, 1.0 eq.) and n-butylamine (0.667 ml, 6.58 mmol, 1.3 eq.) were dissolved in acetonitrile (6 ml) and DMF (6 ml), WSC (1.19 g, 6.08 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 (2.3 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-437c9e07594a46289048cc7c897a32d7
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…