1-Hydroxybenzotriazole → HCID 21084519, compound

HRID 348771

Reaction equation

HRID 348771 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[NH:47][CH2:48][CH2:49][CH3:50])[C:42]#[N:43]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:15])[NH:38][C:39]1[CH:40]=[C:41]([C:42]#[N:43])[CH:44]=[CH:45][C:46]=1[NH:47][CH2:48][CH2:49][CH3:50])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223802993-Amino-4-(propylamino)benzonitrile

Product 1

HCID 21084519HCID 21084519, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In chloroform (5.0 ml), 5-t-butoxycarbonylaminovaleric acid (387 mg), WSCI hydrochloride (466 mg), and HOBt (328.3 mg) were dissolved. Then, the solution was stirred at room temperature for 1 hour. A solution (3.0 ml) of 3-amino-4-propylaminobenzonitrile (283 mg) in chloroform was dropped in this solution. Then, the solution was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and then washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous ammonium chloride solution, and saturated saline solution, followed by drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound as a colorless viscous substance.

Workup

  1. stirringThen, the solution was stirred overnight at room temperature
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a saturated aqueous sodium bicarbonate solution
  6. dry with materialby drying with anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)
  10. customobtaining the subject compound as a colorless viscous substance

Sources & evidence

ORD record
ord-fcdeb3cccc294ca7b5bb4b01e3dabb75
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Linked notes

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