Production Method 1

35112-28-8

1878-66-6

94171-11-6

Reaction Conditions

1.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -60 °C; 1 h, -60 °C
1.2 -60 °C; 40 min, -60 °C; -60 °C → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Preparation of N-[(4,5-diphenyl-2-thiophenyl)methyl]amine derivatives as antagonists of CB1 cannabinoid receptors and their therapeutic application

, France, , ,

Production Method 2

6574-98-7

622-95-7

94171-11-6

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Diethyl ether ;  10 min, rt; 2 h, rt
1.2 Solvents: Diethyl ether ;  rt; overnight, rt; 3 h, reflux

Reference

Preparation of substituted pyrimidines for treating disorders mediated by the Cannabinoid-1 receptor

, World Intellectual Property Organization, , ,

Production Method 3

35112-28-8

1878-66-6

94171-11-6

Reaction Conditions

1.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  < -40 °C; 90 min, -70 °C
1.2 20 min, -70 °C; 40 min, -70 °C; -70 °C → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Preparation of 4,5-diarylimidazole derivatives as cannabinoid receptor modulators

, World Intellectual Property Organization, , ,

Production Method 4

94171-11-6

Reaction Conditions

Reference

Preparation of 2-arylcarbonyl- and 2-heteroarylcarbonylpyrimidine derivatives as cannabinoid receptor ligands

, United States, , ,

Production Method 5

6574-98-7

94171-11-6

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Diethyl ether ;  90 min, reflux; reflux → rt
1.2 Solvents: Toluene ;  rt; 2 h, 135 °C; 135 °C → rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  overnight, rt

Reference

Bioisosteric Replacements of the Pyrazole Moiety of Rimonabant: Synthesis, Biological Properties, and Molecular Modeling Investigations of Thiazoles, Triazoles, and Imidazoles as Potent and Selective CB1 Cannabinoid Receptor Antagonists

Lange, Jos H. M.; van Stuivenberg, Herman H.; Coolen, Hein K. A. C.; Adolfs, Tiny J. P.; McCreary, Andrew C.; et al, Journal of Medicinal Chemistry, 2005, 48(6), 1823-1838

Production Method 6

35112-28-8

1878-66-6

94171-11-6

Reaction Conditions

1.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -20 °C
1.2 -

Reference

Synthesis of functionalized 1,8-naphthyridinones and their evaluation as novel, orally active CB1 receptor inverse agonists

Debenham, John S.; Madsen-Duggan, Christina B.; Walsh, Thomas F.; Wang, Junying; Tong, Xinchun; et al, Bioorganic & Medicinal Chemistry Letters, 2006, 16(3), 681-685

Production Method 7

6574-98-7

94171-11-6

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Diethyl ether ;  reflux; reflux → rt
1.2 Solvents: Toluene ;  rt; rt → 135 °C; 2 h, reflux; reflux → rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  cooled

Reference

Thiazole derivatives having cb1-antagonistic, agonistic or partial agonistic activity

, World Intellectual Property Organization, , ,

Production Method 8

25026-34-0

94171-11-6

Reaction Conditions

1.1 Reagents: Aluminum chloride ;  10 min, 0 °C; overnight, 0 °C → rt

Reference

Scaffold hopping, synthesis and structure-activity relationships of 5,6-diaryl-pyrazine-2-amide derivatives: A novel series of CB1 receptor antagonists

Bostroem, Jonas; Berggren, Kristina; Elebring, Thomas; Greasley, Peter J.; Wilstermann, Michael, Bioorganic & Medicinal Chemistry, 2007, 15(12), 4077-4084

Production Method 9

25026-34-0

94171-11-6

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: 1,3-Dichlorobenzene ;  overnight, 25 °C

Reference

Preparation of diarylpyrazinecarboxamides as CB1 receptor antagonists

, World Intellectual Property Organization, , ,

Production Method 10

35112-28-8

1878-66-6

94171-11-6

Reaction Conditions

1.1 Reagents: Sodium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  rt → -60 °C; -60 °C; 1 h, -60 °C
1.2 -60 °C; 40 min, -60 °C; -60 °C → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Preparation of N-[(4,5-diphenyl-2-thiophenyl)methyl]sulfonamide derivatives as antagonists of CB1 cannabinoid receptors and their therapeutic application

, France, , ,

Production Method 11

107732-22-9

94171-11-6

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Chromic acid (H2CrO4) Solvents: Acetone ,  Water ;  15 min, cooled; 30 min, cooled
1.2 Reagents: Isopropanol

Reference

Preparation of pyrimidine derivatives as cannabinoid receptor ligands

, World Intellectual Property Organization, , ,

2-(4-Chlorophenyl)-1-(2,4-Dichlorophenyl)Ethanone Raw materials

• 2,4-Dichlorobenzonitrile
• Methyl 2,4-dichlorobenzoate
• 4-Chlorophenylacetyl chloride
• 1-(bromomethyl)-4-chloro-benzene
• 4-Chlorophenylacetic acid

2-(4-Chlorophenyl)-1-(2,4-Dichlorophenyl)Ethanone Preparation Products

• 2-(4-Chlorophenyl)-1-(2,4-Dichlorophenyl)Ethanone (94171-11-6)

• 1. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
  LarsBanko,AlfredLudwig
• 2. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
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  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 4. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
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  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339

• 72867-72-2(2'-2'-Chloro-2-phenylacetophenone)
• 7504-29-2(&nbsp;)
• 99846-93-2(1-(2,5-dichlorophenyl)propan-1-one)
• 92152-98-2(2-(2-chlorophenyl)-1-(4-chlorophenyl)ethanone)
• 84126-33-0(Ethanone, 2-(2,6-dichlorophenyl)-1-phenyl-)
• 6323-18-8(1-(2-Chlorophenyl)propan-1-one)
• 37885-41-9(1-(2,4-Dichlorophenyl)propan-1-one)
• 57479-60-4(2-(2-Chlorophenyl)-1-phenylethan-1-one)
• 654682-18-5(1-(4-Chlorophenyl)-2-(2,4-Dichlorophenyl)Ethanone)
• 77778-75-7(Ethanone, 1,2-bis(2-chlorophenyl)-)