1-Hydroxybenzotriazole → N-(2-amino-5-cyano-phenyl)-4-dipropylaminomethyl-benzamide

HRID 2080794Notes

Reaction equation

HRID 2080794 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH2:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[NH2:49])[C:44]#[N:45]>C(Cl)(Cl)Cl>[NH2:49][C:48]1[CH:47]=[CH:46][C:43]([C:44]#[N:45])=[CH:42][C:41]=1[NH:40][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH3:7])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 7372853,4-DiaminobenzonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167713874-[(Dipropylamino)methyl]benzoic acid

Product 1

HCID 23155606N-(2-amino-5-cyano-phenyl)-4-dipropylaminomethyl-benzamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound (1.01 g) obtained in Example 29-3, WSCI hydrochloride (973 mg), and HOBt (894 mg) were dissolved in chloroform (30 ml), and the whole was stirred for 2 hours. Then, the compound (445 mg) obtained in Example 29-1 was added thereto and the whole was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. Then, the residue was dissolved in chloroform and washed with a saturated ammonium chloride aqueous solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution. After that, the resultant was dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (613 mg) as an orange solid.

Workup

  1. stirringthe whole was stirred at room temperature for 3 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThen, the residue was dissolved in chloroform
  5. washwashed with a saturated ammonium chloride aqueous solution
  6. dry with materialAfter that, the resultant was dried with anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-fcd4a3a9b09243ab9f077dcc5427f44b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…