Triethylamine → 2-Chloro-N-[2-(2-chloro-phenyl)-ethyl]-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-YL)-benzamide

HRID 1767580Notes

Reaction equation

HRID 1767580 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[NH:14][N:13]=[CH:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:39][C:40]1[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=1[CH2:42][CH2:43][NH2:44].C(N(CC)CC)C>CN(C)C=O.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[NH:14][N:13]=[CH:12]2)=[CH:7][C:3]=1[C:4]([NH:44][CH2:43][CH2:42][C:41]1[CH:45]=[CH:46][CH:47]=[CH:48][C:40]=1[Cl:39])=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 831172-(2-Chlorophenyl)ethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 210939062-Chloro-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid

Product 1

HCID 210939082-Chloro-N-[2-(2-chloro-phenyl)-ethyl]-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-YL)-benzamideYield 95.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid (0.028 g, 0.117 mmol) in anhydrous dimethyl formamide (DMF) (4 mL) was added 1-hydroxybenzotriazole (0.018 g, 0.14 mmol). After stirring at room temperature for 10 minutes, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.025 g, 0.13 mmol) was added. After stirring at room temperature for 30 minutes, 2-chlorophenethylamine (0.018 g, 0.12 mmol) and triethylamine (0.012 g, 0.12 mmol) were added and the mixture stirred at room temperature overnight. The reaction mixture was diluted with EtOAc, washed sequentially with water and brine, and dried over sodium sulfate. Removal of solvent in vacuo followed by purification by reverse phase HPLC yielded 0.042 g (10%) of the title compound as a colorless solid. 1H NMR (300 MHz, CDCl3) δ (m, 2H), 3.45 (m, 2H), 7.25 (m, 2H), 7.35 (m, 2H), 7.60 (d, J=7.9 Hz, 1H), 7.76 (s, 1H), 7.78 (s, 1H), 8.43 (s, 1H) and 8.64 (m, 1H). Mass Spectrum (M−H) 3:1 Ratio of 375 and 377.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. stirringthe mixture stirred at room temperature overnight
  3. washwashed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of solvent in vacuo
  6. customfollowed by purification by reverse phase HPLC

Sources & evidence

ORD record
ord-cd013dbbbc354306adb9ade49134b6a6
Source dataset
uspto-grants-2007_06
Patent number
US07235549B2

Reaction notes

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