Production Method 1

19500-02-8

912347-94-5

Reaction Conditions

1.1 Reagents: Boron trichloride Solvents: Dichloromethane ,  p-Xylene ;  30 min, 0 °C
1.2 30 min, 0 °C
1.3 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 45 min, 0 °C; 0 °C → 70 °C; 18 h, 70 °C; 70 °C → rt
1.4 Reagents: Water ;  rt; rt → 70 °C; 1 h, 70 °C

Reference

Discovery of novel urea-based hepatitis C protease inhibitors with high potency against protease-inhibitor-resistant mutants

Kazmierski, Wieslaw M.; et al, Journal of Medicinal Chemistry, 2012, 55(7), 3021-3026

Production Method 2

164082-77-3

912347-94-5

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  20 °C
2.1 Catalysts: Boron trichloride Solvents: Xylene ;  0 °C
2.2 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  0 °C → 70 °C

Reference

Discovery of novel potent and selective dipeptide hepatitis C virus NS3/4A serine protease inhibitors

Raboisson, Pierre; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(18), 5095-5100

Production Method 3

5460-31-1

912347-94-5

Reaction Conditions

1.1 Reagents: Sodium hydride Catalysts: Tetrabutylammonium bromide Solvents: Water ;  0.5 h, rt
1.2 2 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  0.5 h, rt
2.1 Reagents: Aluminum chloride Solvents: 1,2-Dichloroethane ;  0.5 h, cooled
2.2 8 h, cooled
3.1 Reagents: Iron ,  Ammonium chloride Solvents: Ethanol ;  0.5 h, reflux

Reference

Synthesis of 2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol

An, Chenhong; et al, Zhongguo Yiyao Gongye Zazhi, 2015, 46(10), 1069-1072

Production Method 4

55289-06-0

912347-94-5

Reaction Conditions

1.1 Reagents: Triethylamine ,  Diphenylphosphoryl azide Solvents: Toluene ;  100 °C
1.2 Solvents: Toluene ;  100 °C
2.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  20 °C
3.1 Reagents: Boron trichloride Solvents: Xylene ;  0 °C
3.2 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 - 70 °C

Reference

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

Raboisson, Pierre; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(17), 4853-4858

Production Method 5

1640962-73-7

912347-94-5

Reaction Conditions

1.1 Reagents: Iron ,  Ammonium chloride Solvents: Ethanol ;  0.5 h, reflux

Reference

Synthesis of 2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol

An, Chenhong; et al, Zhongguo Yiyao Gongye Zazhi, 2015, 46(10), 1069-1072

Production Method 6

19500-02-8

912347-94-5

Reaction Conditions

1.1 Catalysts: Boron trichloride Solvents: Xylene ;  0 °C
1.2 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  0 °C → 70 °C

Reference

Discovery of novel potent and selective dipeptide hepatitis C virus NS3/4A serine protease inhibitors

Raboisson, Pierre; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(18), 5095-5100

Production Method 7

19500-02-8

912347-94-5

Reaction Conditions

1.1 Reagents: Boron trichloride Solvents: Xylene ;  0 °C
1.2 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 - 70 °C

Reference

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

Raboisson, Pierre; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(17), 4853-4858

Production Method 8

164082-77-3

912347-94-5

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  20 °C
2.1 Reagents: Boron trichloride Solvents: Xylene ;  0 °C
2.2 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 - 70 °C

Reference

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

Raboisson, Pierre; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(17), 4853-4858

Production Method 9

4837-88-1

912347-94-5

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: 1,2-Dichloroethane ;  0.5 h, cooled
1.2 8 h, cooled
2.1 Reagents: Iron ,  Ammonium chloride Solvents: Ethanol ;  0.5 h, reflux

Reference

Synthesis of 2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol

An, Chenhong; et al, Zhongguo Yiyao Gongye Zazhi, 2015, 46(10), 1069-1072

Production Method 10

55289-06-0

912347-94-5

Reaction Conditions

1.1 Reagents: Triethylamine ,  Diphenylphosphoryl azide Solvents: Toluene ;  100 °C
1.2 Solvents: Toluene ;  100 °C
2.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  20 °C
3.1 Catalysts: Boron trichloride Solvents: Xylene ;  0 °C
3.2 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  0 °C → 70 °C

Reference

Discovery of novel potent and selective dipeptide hepatitis C virus NS3/4A serine protease inhibitors

Raboisson, Pierre; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(18), 5095-5100

1-(2-Amino-4-methoxy-3-methylphenyl)ethanone Raw materials

• 1-methoxy-2-methyl-3-nitro-benzene
• 2-Methyl-3-nitrophenol
• 3-Methoxy-2-methylbenzoic acid
• tert-Butyl (3-methoxy-2-methylphenyl)carbamate
• 3-Methoxy-2-methylaniline
• Ethanone, 1-(4-methoxy-3-methyl-2-nitrophenyl)-

1-(2-Amino-4-methoxy-3-methylphenyl)ethanone Preparation Products

• 1-(2-Amino-4-methoxy-3-methylphenyl)ethanone (912347-94-5)

• 1. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
• 2. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
• 3. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 4. Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications
  Partha Laskar,Christine Dufès Nanoscale Adv., 2021,3, 6007-6026
• 5. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

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