4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide

Base Information

• Chemical Name: 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide
• CAS No.: 1300694-21-6
• Molecular Formula: C₂₅H₂₄ClN₃O₂
• Molecular Weight: 433.937
• Mol file: 1300694-21-6.mol

Synonyms:4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide

Chemical Property of 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide

There total 17 articles about 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (1300031-52-0) → 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide (1300694-21-6)

Guidance literature:

With N-ethylmorpholine;; ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 20h;

Reference yield:

4-bromo-aniline (106-40-1) → 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide (1300694-21-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (R-BINAP)ditriflatebis(acetonitrile)palladium(ll) / toluene / 0.33 h / Inert atmosphere

1.2: 16 h

2.1: sodium tetrahydroborate; magnesium(II) chloride hexahydrate; water / ethanol / 2 h / -10 - 20 °C

2.2: 1 h / 20 °C

3.1: pyridine / dichloromethane / 16 h / 20 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane

4.2: 6 h / 105 °C / Inert atmosphere

5.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 °C / Cooling with ice

5.2: 0.51 h / 0 °C

6.1: sodium t-butanolate / bis(dibenzylideneacetone)-palladium⁽⁰⁾; DavePhos / toluene / 16 h / 70 °C / Inert atmosphere

6.2: 0.17 h

7.1: water; sodium hydroxide / ethanol / 2 h / 20 °C

7.2: pH 1

8.1: N-ethylmorpholine;; ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 20 °C

With N-ethylmorpholine;; pyridine; aluminum (III) chloride; sodium tetrahydroborate; magnesium(II) chloride hexahydrate; ammonia; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; sodium t-butanolate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (R-BINAP)ditriflatebis(acetonitrile)palladium(ll); bis(dibenzylideneacetone)-palladium⁽⁰⁾; DavePhos; In 1,2-dimethoxyethane; ethanol; dichloromethane; toluene;

Reference yield:

bromobenzene (108-86-1,52753-63-6) → 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzamide (1300694-21-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: caesium carbonate / toluene / 0.75 h / Inert atmosphere

1.2: 16.75 h / 80 °C / Inert atmosphere

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Cooling with ice

3.1: sulfuric acid / toluene / 2 h / 60 °C

4.1: lithium tert-butoxide / tetrahydrofuran; ethyl acetate / 0.5 h

5.1: sodium tetrahydroborate; magnesium(II) chloride hexahydrate; water / ethanol / 2 h / -10 - 20 °C

5.2: 1 h / 20 °C

6.1: pyridine / dichloromethane / 16 h / 20 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane

7.2: 6 h / 105 °C / Inert atmosphere

8.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 °C / Cooling with ice

8.2: 0.51 h / 0 °C

9.1: sodium t-butanolate / bis(dibenzylideneacetone)-palladium⁽⁰⁾; DavePhos / toluene / 16 h / 70 °C / Inert atmosphere

9.2: 0.17 h

10.1: water; sodium hydroxide / ethanol / 2 h / 20 °C

10.2: pH 1

11.1: N-ethylmorpholine;; ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 20 °C

With N-ethylmorpholine;; pyridine; aluminum (III) chloride; sodium tetrahydroborate; N-Bromosuccinimide; magnesium(II) chloride hexahydrate; sulfuric acid; ammonia; water; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; sodium t-butanolate; lithium tert-butoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(dibenzylideneacetone)-palladium⁽⁰⁾; DavePhos; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

upstream raw materials:

4-bromo-aniline

bromobenzene

bromochlorobenzene

(S)-3-(N-phenylamino)-butyronitrile