6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chloroph enyl)-1-methyl-quinolin-2-one

Base Information

• Chemical Name: 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chloroph enyl)-1-methyl-quinolin-2-one
• CAS No.: 192185-68-5
• Molecular Formula: C27H22 Cl2 N4 O
• Molecular Weight: 489.404
• Mol file: 192185-68-5.mol

Synonyms:R 115777

Chemical Property of 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chloroph enyl)-1-methyl-quinolin-2-one

Chemical Property:

• Vapor Pressure: 1.94E-18mmHg at 25°C
• Boiling Point: 681.7°Cat760mmHg
• Flash Point: 366.1°C
• PSA: 65.84000
• Density: 1.33g/cm³
• LogP: 6.19670

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chloroph enyl)-1-methyl-quinolin-2-one

There total 24 articles about 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chloroph enyl)-1-methyl-quinolin-2-one 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: 85.0%

(±)-4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy-(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone monohydrochloride → 6-[amino(4-chlorophenyl)-1-methyl-1H-imidazol-5-ylmethyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (192185-68-5,192185-72-1)

Guidance literature:

(±)-4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy-(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone monohydrochloride; With thionyl chloride; at 20 - 45 ℃; for 3h;

With ammonia; In methanol; at 12 - 45 ℃; for 15h;

Reference yield:

3-chloro-benzeneacetonitrile (1529-41-5) → 6-[amino(4-chlorophenyl)-1-methyl-1H-imidazol-5-ylmethyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (192185-68-5,192185-72-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 35 percent / NaOH / methanol / 16 h / 20 °C

2.1: 85 percent / titanium(III) chloride / H₂O; tetrahydrofuran / 2 h / 20 °C

3.1: 100 percent / toluene / 110 °C

4.1: 81 percent / t-BuOK / 1,2-dimethoxy-ethane / 16 h / 20 °C

5.1: 83 percent / phosphorus oxychloride / 16 h / 80 °C

6.1: 86 percent / sodium methoxide / 16 h / 60 °C

7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 °C

7.2: 75 percent / tetrahydrofuran / 0.5 h / -70 °C

8.1: 80 percent / aq. HCl; MeOH / 72 h / 60 °C

9.1: 75 percent / benzyltriethylammonium chloride; aq. NaOH / tetrahydrofuran / 16 h / 20 °C

10.1: n-butyllithium; triethylsilyl chloride / tetrahydrofuran; hexane / -78 - 20 °C

10.2: tetrahydrofuran; hexane / 1 h / -78 °C

10.3: 52 percent / water / tetrahydrofuran; hexane / -50 °C

11.1: 3.49 g / thionyl chloride / 40 °C

12.1: ammonia; methanol / 20 h / 22 °C

With hydrogenchloride; methanol; sodium hydroxide; n-butyllithium; thionyl chloride; triethylsilyl chloride; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; ammonia; sodium methylate; titanium(III) chloride; trichlorophosphate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water; toluene;

DOI:10.1002/ejoc.200300538

Reference yield:

(4-Chlorophenyl)(4-nitrophenyl)methanone (7497-60-1) → 6-[amino(4-chlorophenyl)-1-methyl-1H-imidazol-5-ylmethyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (192185-68-5,192185-72-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98 percent / para-toluenesulfonic acid / toluene / 24 h / 110 °C

2.1: 86 percent / NaOH / methanol / 1 h / 60 °C

3.1: 100 percent / titanium(III) chloride / H₂O; tetrahydrofuran / 16 h / 20 °C

4.1: 60 g / toluene / 20 h / 120 °C

5.1: 87 percent / t-BuOK / 1,2-dimethoxy-ethane / 3 h / 20 °C

6.1: 75 percent / benzyltriethylammonium chloride; aq. NaOH / tetrahydrofuran / 16 h / 20 °C

7.1: n-butyllithium; triethylsilyl chloride / tetrahydrofuran; hexane / -78 - 20 °C

7.2: tetrahydrofuran; hexane / 1 h / -78 °C

7.3: 52 percent / water / tetrahydrofuran; hexane / -50 °C

8.1: 3.49 g / thionyl chloride / 40 °C

9.1: ammonia; methanol / 20 h / 22 °C

With methanol; sodium hydroxide; n-butyllithium; thionyl chloride; triethylsilyl chloride; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; ammonia; titanium(III) chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water; toluene;

DOI:10.1002/ejoc.200300538

upstream raw materials:

3-chloro-benzeneacetonitrile

(4-Chlorophenyl)(4-nitrophenyl)methanone

(2-amino-5-bromo-phenyl)-(3-chloro-phenyl)-methanone

para-nitrophenyl bromide

Downstream raw materials:

tipifarnib

Refernces

• 1、 Angibaud, Patrick R.,Venet, Marc G.,Filliers, Walter,Broeckx, Rudy,Ligny, Yannick A.,Muller, Philippe,Poncelet, Virginie S.,End, Dave W.. "Synthesis Routes Towards the Farnesyl Protein Transferase Inhibitor ZARNESTRA". . p. 479 - 486. Retrieved 2007/10/03.
• 2、 -. "Farnesyl protein transferase inhibiting (imidazol-5-yl)methyl-2-quionlinone derivatives". . . Retrieved 2008/06/13.