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Copper-Promoted O‐Arylation of the Phenol Side Chain of Tyrosine using Triarylbismuthines


Adrien Le Roch, Martin Hébert, Alexandre Gagnon

EurJOC, 2020, 33, 5363 DOI: 10.1002/ejoc.202000790

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Copper-Promoted N‐Arylation of the Indole Side Chain of Tryptophan using Triarylbismuthines


Adrien Le Roch, Hwai-Chien Chan, Alexandre Gagnon

EurJOC, 2020, 36, 5815 DOI: 10.1002/ejoc.202000667

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Heavy metal orchestration


Adrien Le Roch, Alexandre Gagnon

Nature Chemistry, 202012, 223-224 DOI: 10.1038/s41557-020-0434-3

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Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acids


Emeline Benoit, Ahmed Fnaiche, Alexandre Gagnon

Beilstein J. Org. Chem.201915, 1162 DOI: 10.3762/bjoc.15.113 

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First use of an organobismuth reagent in C(sp3)–S bond formation: Access to aryl cyclopropyl sulfides via copper-catalyzed S-cyclopropylation of thiophenols using tricyclopropylbismuth


Emeline Benoit, Bianca Bueno, Catherine Choinière, Alexandre Gagnon

J. Organomet. Chem., 2019, 893, 72 DOI: 10.1016/j.jorganchem.2019.04.032

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Synthesis of NSC 106084 and NSC 14778 and evaluation of their DNMT inhibitory activity


Maxime Leroy, Léa Mélin, Steven R. LaPlante, José L. Medina-Franco, Alexandre Gagnon

Bioorg. Med. Chem. Lett.201929, 826 DOI: 10.1016/j.bmcl.2019.01.022

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Copper-Catalyzed Beta-Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl-Carbamates


Simon Ricard, Alexandre Gagnon, Benoit Daoust

ChemistrySelect2018, 4923 DOI: 10.1002/slct.201800824

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Bismuth Compounds


Alexandre Gagnon, Emeline Benoit, Adrien Le Roch

Science of synthesis knowledge updates 2018/4 

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Palladium-Catalyzed Carbonylative Cross-Coupling Reaction between Aryl(Heteroaryl)iodides and Tricyclopropylbismuth: Expedient Access to Aryl Cyclopropylketones

Emeline Benoit, Julien Dansereau, Alexandre Gagnon

Synlett, 2017, 2833 DOI: 10.1055/s-0036-1590832

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Synthesis of Highly Functionalized Diaryl Ketones by Palladium-Catalyzed Carbonylative Cross-Coupling Reaction Between Triarylbismuthines and Aryl(Heteroaryl) Iodides

Julien Dansereau, Stéphane Gautreau, Alexandre Gagnon

Chemistry Select, 2017, 2593 DOI: 10.1002/slct.201700438

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Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

Alexandre Gagnon, Julien Dansereau, Adrien Le Roch

Synthesis201749, 1707 DOI: 10.1055/s-0036-1589482

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Preparation of 3-O-aryl chloramphenicol derivatives via copper-catalyzed O-arylation of (1R,2R)-(-)-N-BOC-2-amino-1-(4-nitrophenyl)-1,3-propanediol using triarylbismuthines

Tabinda Ahmad, Julien Dansereau, Martin Hébert, Chantal Grand-Maître, Alexandre Larivée, Arshad Siddiqui, Alexandre Gagnon

Tetrahedron Lett.201657, 4284 DOI: 10.1016/j.tetlet.2016.08.021

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Synthesis of Highly Functionalized Triarylbismuthines by Functional Group Manipulation and Use in Palladium- and Copper-Catalyzed Arylation Reactions

Martin Hébert, Pauline Petiot, Emeline Benoit, Julien Dansereau, Tabinda Ahmad, Adrien Le Roch, Xavier Ottenwaelder, Alexandre Gagnon

J. Org. Chem.201681, 5401 DOI: 10.1021/acs.joc.6b00767

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Chapter 3: Drug Discovery Methods

Marie Lopez, Maxime Leroy, Chantal Etievant, Frédéric Ausseil, Alexandre Gagnon, Paola Arimondo

Drug Discovery in Cancer Epigenetics, 2016, 63 DOI: 10.1016/B978-0-12-802208-5.00003-5

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Mechanism-Driven Elaboration of an Enantioselective Bromocyclopropanation Reaction of Allylic Alcohols

Sylvain Taillemaud, Nicolas Diercxsens, Alexandre Gagnon, André B. Charette

Angew. Chem. Int. Ed.2015, 54, 14108 DOI: 10.1002/anie.201506083

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Discovery, design and synthesis of indole-based EZH2 inhibitors

Victor S. Gehling, Rishi G. Vaswani, Christopher G. Nasveschuk, Martin Duplessis, Priyadarshini Iyer, Srividya Balasubramanian, Feng Zhao, Andrew C. Good, Robert Campbell, Christina Lee, Les A. Dakin, Andrew S. Cook, Alexandre Gagnon, Jean-Christophe Harmange, James E. Audia, Richard T. Cummings, Emmanuel Normant, Patrick Trojer, Brian K. Albrecht

Bioorg. Med. Chem. Lett., 2015, 25, 3644 DOI: 10.1016/j.bmcl.2015.06.056

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Aza Follow-ups to BI 207524, a Thumb Pocket 1 HCV NS5B Polymerase Inhibitor. Part 1: Mitigating the Genotoxic Liability of an Aniline Metabolite

Pierre Beaulieu, Gordon Bolger, Martin Duplessis, Alexandre Gagnon, Michel Garneau, Timothy Stammers, George Kukolj, Jianmin Duan

Bioorg. Med. Chem. Lett.201525, 1135 DOI: 10.1016/j.bmcl.2014.12.028

Multi-Parameter Optimization of Aza-follow-ups to BI 207524, a thumb pocket 1 HCV NS5B Polymerase Inhibitor. Part 2: Impact of Lipophilicity on Promiscuity and in vivo Toxicity

Pierre Beaulieu, Gordon Bolger, Dan Deon, Martin Duplessis, Gulrez Fazal, Alexandre Gagnon, Michel Garneau, Steven LaPlante, Timothy Stammers, George Kukolj, Jianmin Duan

Bioorg. Med. Chem. Lett.201525, 1140 DOI: 10.1016/j.bmcl.2014.12.078

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Spontaneous grafting of 9,10-phenanthrenequinone on porous carbon as active electrode material in electrochemical capacitor in alkaline electrolyte

Annaïg Le Comte, Danny Chhin, Alexandre Gagnon, Richard Retoux and Daniel Bélanger 

J. Mater. Chem. A.20154, 1562 DOI: 10.1039/C4TA05536E

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Copper-Catalyzed O-arylation of N-protected 1,2-aminoalcohols using functionalized trivalent organobismuth reagents

Pauline Petiot, Julien Dansereau, Martin Hébert, Imene Khene, Tabinda Ahmad, Samira Samaali, Maxime Leroy, Francis Pinsonneault, Claude Y. Legault and Alexandre Gagnon 

Org. Biomol. Chem.2015, 131322 DOI: 10.1039/C4OB02497D


Copper-Catalyzed N-Arylation of Azoles and Diazoles using Highly Functionalized Trivalent Organobismuth Reagents

Pauline Petiot, Julien Dansereau and Alexandre Gagnon 

RSC Advances2014, 22255 DOI: 10.1039/C4RA02467B

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Discovery and Optimization of Tetramethylpiperidinyl Benzamides as Inhibitors of EZH2

Christopher G. Nasveschuk*, Alexandre Gagnon, Shivani Garapaty-Rao, Srividya Balasubramanian, Robert Campbell, Christina Lee, Feng Zhao, Louise Bergeron, Richard Cummings, Patrick Trojer, James E. Audia, Brian K. Albrecht and Jean-Christophe P. Harmange  

ACS Med. Chem. Lett.2014378 DOI: 10.1021/ml400494b

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Synthesis of Highly Functionalized Diaryl Ethers by Copper-Mediated O-Arylation of Phenols using Trivalent Arylbismuth Reagents

Cynthia Crifar, Pauline Petiot, Tabinda Ahmad and Alexandre Gagnon 

Chem. Eur. J.201420, 2755 DOI: 10.1002/chem.201303684

Palladium-Catalyzed Cross-Coupling Reaction of Trialkylbismuthines with 2-Haloazines and Diazines

Pauline Petiot and Alexandre Gagnon

Heterocycles20141615 DOI: 10.3987/COM-13-S(S)114

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Anthranilic acid-based Thumb Pocket 2 HCV NS5B polymerase inhibitors with sub-micromolar potency in the cell-based replicon assay

Timothy A. Stammers,* René Coulombe, Martin Duplessis, Gulrez Fazal, Alexandre Gagnon, Michel Garneau, Sylvie Goulet, Araz Jakalian, Steven LaPlante, Jean Rancourt, Bounkham Thavonekham, Dominik Wernic, George Kulolg and Pierre Beaulieu

Bioorg. Med. Chem. Lett.2013236879 DOI: 10.1016/j.bmcl.2013.09.102

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Identification of EZH2 and EZH1 Small Molecule Inhibitors with Selective Impact on Diffuse Large B Cell Lymphoma Cell Growth

Shivani Garapaty-Rao, Christopher Nasveschuk, Alexandre Gagnon, Eric Y. Chan, Peter Sandy, Jennifer Busby, Srividya Balasubramanian, Robert Campbell, Feng Zhao, Louise Bergeron, James E. Audia, Brian K. Albrecht, Jean-Christophe Harmange, Richard Cummings and Patrick Trojer

Chem. & Biol.2013201329 DOI: 10.1016/j.chembiol.2013.09.013

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Preparation of phenylethylbenzamide derivatives as modulators of DNMT3 activity

Anzhelika Kabro, Hugo Lachance, Iris Marcoux-Archambault, Valérie Perrier, Vicky Doré, Christina Gros, Véronique Masson, Jean-Marc Gregoire, Frédéric Ausseil, David Cheishvili, Nathalie Bibens Laulan, Yves St-Pierre, Moshe Szyf, Paola B. Arimondo and Alexandre Gagnon

Med. Chem. Commun., 20131562 DOI: 10.1039/C3MD00214D

Palladium-Catalyzed Cross-Coupling Reaction of Functionalized Aryl- and Heteroarylbismuthanes with 2-Halo(or 2-Triflyl)azines and -diazines

Pauline Petiot and Alexandre Gagnon

Eur. J. Org. Chem.2013, 5282 DOI: 10.1002/ejoc.201300850


Alexandre Gagnon

Encyclopedia of Reagents for Organic Synthesis (eROS), 2013 DOI: 10.1002/047084289.rn01539

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Inhibition of HIV-1 capsid assembly: Optimization of the antiviral potency by site selective modifications at N1, C2 and C16 of a 5-(5-furan-2-ylpyrazoly-1-yl)-1H-benzimidazole scaffold

Martin Tremblay, Pierre Bonneau, Yves Bousquet, Patrick DeRoy, Jianmin Duan, Martin Duplessis, Alexandre Gagnon, Michel Garneau, Nathalie Goudreau, Ingrid Guse, Oliver Hucke, Stephen H. Kawai, Christopher T. Lemke, Stephen W. Mason, Bruno Simoneau, Simon Surprenant, Steve Titolo, Christiane Yoakim

Bioorg. Med. Chem. Lett.2012, 22, 7512 DOI: 10.1016/j.bmcl.2012.10.034

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Highly Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes by Using α-Iodo and α-Chloromethylzinc Carbenoids

Louis-Philippe B. Beaulieu, Lucie E. Zimmer, Alexandre Gagnon and André B. Charette

Chem. Eur. J.201214784 DOI: 10.1002/chem.201202528

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Distinct effects of two HIV-1 capsid assembly inhibitor families that bind the same site within the N-terminal domain of the viral CA protein

Christopher Lemke, Steve Titolo, Uta von Schwedler, Nathalie Goudreau, Jean-François Mercier, Elizabeth Wardrop, Anne-Marie Faucher, René Coulombe, Soma S. R. Banik, Lee Fader, Alexandre Gagnon, Stephen H. Kawai, Jean Rancourt, Martin Tremblay, Christiane Yoakim, Bruno Simoneau, Jacques Archambault, Wesley I. Sundquist and Stephen W. Masontte

J. Virol.2012, 866643 DOI: 10.1128/JVI.00493-12

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Alexandre Gagnon

Encyclopedia of Reagents for Organic Synthesis (Online),, 15 mars 2011  DOI: 10.1002/047084289X.m01272

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Discovery of a 1,5-Dihydrobenzo[b][1,4]diazepine-2,4-dione Series of Inhibitors of HIV-1 Capsid Assembly

Lee Fader,* Richard Bethell, Pierre Bonneau, Michael Bös, Yves Bousquet, Michael G. Cordingley, René Coulombe, Patrick Deroy, Anne-Marie Faucher, Alexandre Gagnon, Nathalie Goudreau, Chantal Grand-Maître, Ingrid Guse, Oliver Hucke, Stephen H. Kawai, Jean-Eric Lacoste, Serge Landry, Christopher T. Lemke, Eric Malenfant, Stephen Mason, Sébastien Morin, Jeff O’Meara, Bruno Simoneau, Steve Titolo and Christiane Yoakim

Bioorg. Med. Chem. Lett., 2011, 21, 398 DOI: 10.1016/j.bmcl.2010.10.131

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Csp3-Csp2 Palladium-Catalyzed Cross-Coupling Reaction of Trialkylbismuth Reagents With Aryl, Heteroaryl, and Vinyl Halides and Triflates

Alexandre Gagnon,* Vincent Albert and Martin Duplessis

Synlett, 2010, 19, 2936 DOI: 10.1055/s-0030-1259023

Arylcyclopropanes: Properties, Synthesis and use in Medicinal Chemistry

Alexandre Gagnon,* Martin Duplessis and Lee Fader

Org. Prep. Proc. Int., Invited Review, 201042, 1–69 DOI: 10.1080/00304940903507788

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Investigation on the role of the tetrazole in the binding of thiotetrazolylacetanilides with HIV-1 wild type and K103N/Y181C double mutant reverse transcriptases

Alexandre Gagnon,* Serge Landry, René Coulombe, Araz Jakalian, Ingrid Guse, Bounhkham Thavonekham, Pierre R. Bonneau, Christiane Yoakim and Bruno Simoneau

Bioorg. Med. Chem. Lett. 200919, 1199 DOI: 10.1016/j.bmcl.2008.12.074

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Palladium-catalyzed cross-coupling reaction of tricyclopropylbismuth with aryl halides and triflates

Alexandre Gagnon,* Martin Duplessis, Pamela Alsabeh and Francis Barabé

J. Org. Chem., 200873, 3604 (Highlighted in Synfacts 2008, 7, 744)

 DOI: 10.1021/jo702377h

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Thiotetrazole alkynylacetanilides as potent and bioavailable non-nucleoside inhibitors of the HIV-1 wild-type and K103N/Y181C double mutant reverse transcriptases

Alexandre Gagnon,* Ma’an H. Amad, Pierre R. Bonneau, René Coulombe, Patrick L. DeRoy, Louise Doyon, Jianmin Duan, Michel Garneau, Ingrid Guse, Araz Jakalian, Eric Jolicoeur, Serge Landry, Eric Malenfant, Bruno Simoneau and Christiane Yoakim

Bioorg. Med. Chem. Lett. 200717, 4437 DOI: 10.1016/j.bmcl.2007.06.012

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Direct N-cyclopropylation of cyclic amides and azoles employing a cyclopropylbismuth reagent

Alexandre Gagnon,* Miguel St-Onge, Kelly Little, Martin Duplessis, Francis Barabé

J. Am. Chem. Soc. 2007129, 44 (Highlighted in Synfacts 2007, 3, 302) DOI: 10.1021/ja0676758

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Toward the synthesis of Xestocyclamine A: Investigation on the double-Michael reaction and direct aza Diels-Alder reaction

Heedong Yun, Alexandre Gagnon and Samuel J. Danishefsky

Tetrahedron Lett. 200647, 5311 DOI: 10.1016/j.tetlet.2006.05.126

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Evaluation of diene hierarchies for Diels-Alder reactions en route to Xestocyclamine A: elaboration of the ansa bridge by B-Alkyl Suzuki macrocyclization

Alexandre Gagnon and Samuel J. Danishefsky

Angew. Chem. Int. Ed. 2002, 41, 1581

DOI: 10.1002/1521-3773(20020503)41:9<1581::AID-ANIE1581>3.0.CO;2-F

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First evidence for the formation of a geminal dizinc carbenoid: a highly stereoselective synthesis of 1,2,3-substituted cyclopropanes

André B. Charette,* Alexandre Gagnon and Jean-François Fournier

J. Am. Chem. Soc. 2002, 124, 386 DOI: 10.1021/ja017230d

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(Z)bis-μ-[1-(2-naphthylmethyloxy)propan-2-iminato-O,N:N]bis[bromobis(tetrahydrofuran-O)magnesium] ditoluene solvate

André B. Charette,* Alexandre Gagnon and Francine Bélanger-Gariépy

Acta Cryst. 2000C56, 538 DOI: 10.1107/S0108270100001281

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The stereoselective cyclopropanation of chiral allylic alcohols using a chiral dioxaborolane ligand: A new route to anti-cyclopropylmethanol derivatives

André B. Charette,* Hélène Lebel and Alexandre Gagnon

Tetrahedron, 199955, 8845 DOI: 10.1016/S0040-4020(99)00448-2

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Stereoselective synthesis of α,α-disubstituted amines by a sequential nucleophilic addition to O-protected cyanohydrins

André B. Charette* and Alexandre Gagnon

Tetrahedron Asymmetry, 199910, 1961 DOI: 10.1016/S0957-4166(99)00201-3

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Synthesis of α,α-disubstituted-α-amino acids by double nucleophilic addition to cyanohydrins

André B. Charette,* Alexandre Gagnon, Marc Janes and Christophe Mellon 

Tetrahedron Lett. 199839, 5147 DOI: 10.1016/S0040-4039(98)00983-6


8.   Albrecht, B.K.; Audia, J.E.; Gagnon, A.; Harmange, J.-C.; Nasveschuk, C.G. "Preparation of N-[2-(hydroxyl-4,6-dimethylpyridin-3-yl)methyl]benzamides as Modulators of Methyl Modifying Enzymes" PCT Int. Appl. 2013, WO 2013/075084.

7.   Brian Albrecht, James E. Audia, Alexandre Gagnon, Jean-Christophe Harmange, Christopher G. Nasveschuk “Modulators of methyl modifying enzymes, compositions and uses thereof”, PCT Int. Appl. 2012, WO 2012/068589.

6.   Bruno Simoneau, Patrick Deroy, Lee Fader, Anne-Marie Faucher, Alexandre Gagnon, Chantal Grand-Maître, Stephen Kawai, Serge Landry, Jean-François Mercier, Jean Rancourt “1-Phenyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione derivatives as HIV replication inhibitors and their preparation and use for the treatment of HIV infection”, PCT Int. Appl. 2011, WO 2011/100838.

5.   Pierre L. Beaulieu, Pasquale Forgione, Alexandre Gagnon, Cedrickx Godbout, Marc-André Joly, Montse Llinas-Brunet, Julie Naud, Martin Poirier, Jean Rancourt “Preparation of 2-amido benzoic acid compounds as viral polymerase inhibitors”, PCT Int. Appl. 2009, WO 2009/076747.

4.   Pierre L. Beaulieu, Pasquale Forgione, Alexandre Gagnon, Cedrickx Godbout, Julie Naud, Martin Poirier, Jean Rancourt, Timothy Stammers, Bounkham Thavonekham, “Preparation of substituted carbonylaminobenzoic acid viral polymerase inhibitors”, PCT Int. Appl. 2009, WO 2009/018656.

3.   Christiane Yoakim, Patrick L. DeRoy, Martin Duplessis, Alexandre Gagnon, Sylvie Goulet, Oliver Huecke, Christopher Lemke, Simon Surprenant, “Preparation of pyrazolylbenzimidazole derivatives for use as HIV replication inhibitors”, 2008, WO 2008/067644.

2.   Pierre R. Bonneau, Patrick L. DeRoy, Alexandre Gagnon, Jeffrey O’Meara, Bruno Simoneau, Christiane Yoakim, “Preparation of phenylalkyne derivatives as non nucleoside reverse transcriptase inhibitors for treatment of HIV infection” 2006, US Pat. Appl. Publ., US 2006/069261.

1.   Patrick L. DeRoy, Anne-Marie Faucher, Alexandre Gagnon, Serge Landry, Sébastien Morin, Jeffrey O’Meara, Bruno Simoneau, Bounkham Thavonekham, Christiane Yoakim, “Preparation of acetamide derivatives as reverse transcriptase inhibitors for treatment of HIV”, US Pat. Appl. Publ. 2005, US 2005/118575.