Name: 5409-31-4|3,4-Diethoxybenzoic acid|99%
Brand: Ambeed
SKU: A506387
Rating: 91 (22 reviews)

1
[ 2029-94-9 ]
[ 5409-31-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 3,4-diethoxybenzaldehyde With silver nitrate; sodium hydroxide In methanol; water at 20℃; for 0.5h; Stage #2: With hydrogenchloride In methanol; water
	With potassium permanganate

Reference： [1]Location in patent: experimental part Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]
[2]Hirao [Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1931, vol. 52, p. 26,29][Chem.Abstr., 1931, p. 5156]

2
[ 5409-31-4 ]
[ 2050-46-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1871,vol. 159,p. 243

3
[ 5409-31-4 ]
[ 105905-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; benzene
	With thionyl chloride In dichloromethane for 1h; Heating;
	With thionyl chloride for 0.5h; Heating;

	With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 1h;
	With thionyl chloride In dichloromethane at 20℃; for 1.5h; Reflux;	2-(3,4-diethoxyphenyl)-5-(pyridin-4-yl)-l,3,4-oxadiazole (25) To a stirred solution of 3,4-diethoxybenzoic acid (0.71 mmol, 150 mg) in CH2Cl2 was added SOCl2 at room temperature and the reaction was refluxed for 1.5 h. The mixture was concentrated under reduced pressure. To a stirred suspension OfNa2CO3 (1.42 mmol, 150.52 mg) and pyridine-4-carbohydrazide (0.71 mmol, 97 mg) in NMP (0.8 mL) was added a solution of 3, 4-diethoxybenzoyl chloride (prepare above) in NMP (0.8 mL). The reaction was stirred for 12 h at room temperature, poured to 20 mL of cold H2O and filtered. The precipitated intermediate was dried in vacuo. The solid was added to POCl3 (5 mL) and heated to 70-72 °C for 6h. The solution was poured in an ice-water container and neutralized with a solution of NaOH (2M). The precipitated product was filtered and purified by CC. using CH2Cl2:MeOH (9:1) to yield the product in 67% yield (150mg). 1H NMR (400MHz, CDCl3)δ: 8.84(bs, 2H), 7.99 (d, J=4.4Hz, 2H), 7.67 (dd, J=2.0, 8.4 Hz, IH), 7.64 (d, J=2.0 Hz, IH), 6.98 (d, J=8.4Hz, IH), 4.20 (q, J=7.2 Hz, 2H), 4.18 (q, J=7.2 Hz, 2H), 1.51(t, J=7.2Hz, 3H), 1.50 (t, J=7.2 Hz, 3H). 13C NMR (CDCl3)δ: 165.81, 162.46, 152.51, 150.84, 149.20, 131.52, 128.05, 120.97, 1 15.77, 1 12.78, 11 1.58, 65.05, 64.80, 14.92, 14.85. MS (M+l)
	With thionyl chloride at 90℃; for 3h;
	With thionyl chloride at 80℃; for 4h;
	With thionyl chloride for 2h; Reflux;	29 General procedure for antagonists synthesis (1, 4a-n) General procedure: A mixture of commercial carboxylic acid in freshly distilled thionyl chloride is warmed into reflux for 2 h, then cooled to room temperature and evaporated under vacuum to dryness to afford quantitatively corresponding acid chlorides (3). This crude material might be used without further purification. A mixture of these acid chloride (1.0 equiv) and ammonium thiocyanate (1.0 equiv) is heated in refluxing dry acetone for 1h. Then, the mixture is cooled to room temperature, and a solution of benzimidazole in dry acetone is carefully added. The mixture is warmed again for 1 h, then cooled to 0 °C, and hydrolyzed with ice. The precipitate is washed with cold water and crude material is crystallized into ethanol.
	With thionyl chloride Reflux;

Reference： [1]Kovacs [1942, vol. 1, p. 109,139][Chem.Abstr., 1948, p. 173]
[2]Terada; Motomiya; Yoshioka; Narita; Yasui; Takase [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2437 - 2442]
[3]Sakaguchi; Nishino; Ogawa; Iwanaga; Yasuda; Kato; Ito [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 202 - 211]
[4]Location in patent: experimental part Nakada, Yoshihisa; Ogino, Masaki; Asano, Kouhei; Aoki, Kazuko; Miki, Hiroshi; Yamamoto, Toshihiro; Kato, Koki; Masago, Minori; Tamura, Norikazu; Shimada, Mitsuyuki [Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 5, p. 673 - 679]
[5]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1 Location in patent: Page/Page column 138
[6]Location in patent: experimental part Bland, Nicholas D.; Wang, Cuihua; Tallman, Craig; Gustafson, Alden E.; Wang, Zhouxi; Ashton, Trent D.; Ochiana, Stefan O.; McAllister, Gregory; Cotter, Kristina; Fang, Anna P.; Gechijian, Lara; Garceau, Norman; Gangurde, Rajiv; Ortenberg, Ron; Ondrechen, Mary Jo; Campbell, Robert K.; Pollastri, Michael P. [Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8188 - 8194]
[7]Fang, Fei; Li, Dong-Dong; Li, Jing-Ran; Sun, Jian; Du, Qian-Ru; Gong, Hai-Bin; Zhu, Hai-Liang [RSC Advances, 2013, vol. 3, # 48, p. 26230 - 26240]
[8]Liu, Wang-Qing; Megale, Valentino; Borriello, Lucia; Leforban, Bertrand; Montes, Matthieu; Goldwaser, Elodie; Gresh, Nohad; Piquemal, Jean-Philip; Hadj-Slimane, Reda; Hermine, Olivier; Garbay, Christiane; Raynaud, Francoise; Lepelletier, Yves; Demange, Luc [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4254 - 4259]
[9]Banoglu, Erden; Ercanlı, Taner; Gür Maz, Tuğçe; Vullo, Daniela; Bonardi, Alessandro; Gratteri, Paola; Supuran, Claudiu T. [ChemMedChem, 2022, vol. 17, # 10]

4
[ 75332-44-4 ]
[ 5409-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide
	With potassium hydroxide In ethanol for 2.5h; Heating; Yield given;

Reference： [1]Herzig [Monatshefte fur Chemie, 1884, vol. 5, p. 75][Monatshefte fuer Chemie, 1888, vol. 9, p. 541] Koelle [Justus Liebigs Annalen der Chemie, 1871, vol. 159, p. 243]
[2]Rowe, Kathryn E.; Bruce, Duncan W. [Journal of Materials Chemistry, 1998, vol. 8, # 2, p. 331 - 341]

5
[ 5409-31-4 ]
[ 83459-29-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium aluminium tetrahydride In diethyl ether a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h;

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

6
[ 5409-31-4 ]
[ 173943-90-3 ]
(+/-)-N-<2-(3,4-dichlorophenyl)-4-(spiro<isobenzofuran-1(3H),4'-piperidin>-1'-yl)butyl>-3,4-diethoxy-N-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 6h; Ambient temperature;

Reference： [1]Kubota, Hirokazu; Kakefuda, Akio; Okamoto, Yoshinori; Fujii, Masahiro; Yamamoto, Osamu; Yamagiwa, Yoko; Orita, Masaya; Ikeda, Ken; Takeuchi, Makoto; Shibanuma, Tadao; Isomura, Yasuo [Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 10, p. 1538 - 1544]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate at 140 - 150℃; im geschlossenen Rohr;

8
[ 5409-31-4 ]
[ 103796-34-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With nitric acid; tin(ll) chloride In dichloromethane at -25℃; for 0.0833333h;	4 To a mixture of 11.4 ml of Tin(IV) chloride (0.097 mol) and 0.1 ml of fumming nitric acid (0.155 mol) in 100 ml of dichloromethane was added dropwise 17 g of compound 15 (0.08 mol) in 100 ml of dichloromethane at -25° C. with stirring. After 5 min, 200 ml of water was added and the product was extracted with dichloromethane and ethyl acetate. The organic layer was dried over MgSO4 and concentrated to give compound 16 (16.4 g, 85%). 1H-NMR (300 MHz, CDCl3): δ 7.28 (s, 1H), 6.82 (s, 1H), 4.13 (m, 4H), 1.46 (m, 6H).
67%	With nitric acid; acetic acid at 20℃; for 2.08333h;
27%	With nitric acid; acetic acid at 20℃; for 1h;

27%

With nitric acid; acetic acid at 20℃; for 1h;

A 4,5-diethoxy-2-nitrobenzoic acid General procedure: A flask immersed in a room-temperature water bath was charged with 3,4- diethoxybenzoic acid (1 .29 g. 6.1 mmol) and acetic acid (glacial, 5.2ml_). HNO3 (70%, 5.4 mL) was slowly added and stirred for 60 min at room temperature. The reaction was quenched upon addition of ice. A yellow precipitate formed that was filtered and washed with H2O. Recrystallization from DCM gave 4,5-diethoxy-2- nitrobenzoic acid as an off-white solid (424 mg, 1 .7 mmol, 27%). 1 H NMR (600 MHz, CDCIs) δ 10.29 (s, 1 H), 7.37 (s, 1 H), 7.24 (s, 1 H), 4.24 - 4.17 (m, 4H), 1 .51 (t, J = 7.0 Hz, 6H). 13C NMR (151 MHz, CDCI3) δ 170.6, 151 .6, 150.9, 142.2, 1 19.0, 1 12.5, 108.1 , 65.4, 65.4, 14.5, 14.4. HRMS (+) calcd for (M+H)+ 256.0816. Found 256.0818.

Reference： [1]Current Patent Assignee: REXAHN PHARMACEUTICALS, INC. - US2005/187231, 2005, A1 Location in patent: Page/Page column 18
[2]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]
[3]Kitamura, Seiya; Owensby, Anna; Wall, Daniel; Wolan, Dennis W. [Cell Chemical Biology, 2018, vol. 25, # 3, p. 301 - 12,308]
[4]Current Patent Assignee: SCRIPPS RESEARCH - WO2019/10165, 2019, A1 Location in patent: Page/Page column 26

9
[ 5409-31-4 ]
[ 390381-60-9 ]
N-{(E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-enyl}-2-(1H-indol-3-yl)-3,4-diethoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,4-diethoxybenzoic acid With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In tetrahydrofuran at 20℃; for 24h; Stage #2: With N-ethyl-N,N-diisopropylamine; cyanomethyl bromide In 1-methyl-pyrrolidin-2-one Stage #3: (2R,3S,4R,5R)-2-[(E)-3-aminoprop-1-enyl]-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diol In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃;

Reference： [1]Heidler, Philipp; Link, Andreas [Australian Journal of Chemistry, 2005, vol. 58, # 3, p. 182 - 187]

10
[ 5409-31-4 ]
(3-chloro-phenyl)-(6,7-diethoxy-quinazolin-4-yl)-amine; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 65 percent / dimethylformamide / 0.67 h / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

11
[ 5409-31-4 ]
(6,7-diethoxy-quinazolin-4-yl)-(2-fluoro-phenyl)-amine; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 61 percent / dimethylformamide / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

12
[ 5409-31-4 ]
(6,7-diethoxy-quinazolin-4-yl)-(4-fluoro-phenyl)-amine; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 97 percent / dimethylformamide / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

13
[ 5409-31-4 ]
(6,7-diethoxy-quinazolin-4-yl)-(3-fluoro-phenyl)-amine; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 77 percent / dimethylformamide / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

14
[ 5409-31-4 ]
4-[(4'-fluorobenzyl)amino]-6,7-diethoxyquinazoline hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 84 percent / dimethylformamide / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

15
[ 5409-31-4 ]
(6,7-diethoxy-quinazolin-4-yl)-(3-fluoro-5-trifluoromethyl-phenyl)-amine; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 92 percent / dimethylformamide / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

16
[ 5409-31-4 ]
[ 20197-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

17
[ 5409-31-4 ]
[ 162363-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

18
[ 5409-31-4 ]
4-(3'-bromoanilino)-6,7-diethoxyquinazoline hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 50 percent / dimethylformamide / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

19
[ 5409-31-4 ]
4-(3'-iodoanilino)-6,7-diethoxyquinazoline hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating 5: 95 percent / dimethylformamide / 80 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

20
[ 5409-31-4 ]
[ 179246-15-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 67 percent / HNO₃; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl₂; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C

Reference： [1]VanBrocklin, Henry F.; Lim, John K.; Coffing, Stephanie L.; Hom, Darren L.; Negash, Kitaw; Ono, Michele Y.; Gilmore, Jennifer L.; Bryant, Ianthe; Riese II, David J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7445 - 7456]

21
[ 3943-89-3 ]
[ 5409-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃ / butan-2-one / 84 h / Heating 2: KOH / ethanol / 2.5 h / Heating

Reference： [1]Rowe, Kathryn E.; Bruce, Duncan W. [Journal of Materials Chemistry, 1998, vol. 8, # 2, p. 331 - 341]

22
[ 5409-31-4 ]
3,4-Diethoxy-benzoic acid 4-hydroxy-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dicyclohexylcarbodiimide, N,N-dimethylaminopyridine / CH₂Cl₂ / 24 h / Ambient temperature 2: H₂, Et₃N / 10percent Pd/C / tetrahydrofuran / Ambient temperature

Reference： [1]Rowe, Kathryn E.; Bruce, Duncan W. [Journal of Materials Chemistry, 1998, vol. 8, # 2, p. 331 - 341]

23
[ 5409-31-4 ]
[2,2']Bipyridinyl-5,5'-dicarboxylic acid bis-[4-(3,4-diethoxy-benzoyloxy)-phenyl] ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dicyclohexylcarbodiimide, N,N-dimethylaminopyridine / CH₂Cl₂ / 24 h / Ambient temperature 2: H₂, Et₃N / 10percent Pd/C / tetrahydrofuran / Ambient temperature 3: 15 percent / Et₃N / toluene / Heating

Reference： [1]Rowe, Kathryn E.; Bruce, Duncan W. [Journal of Materials Chemistry, 1998, vol. 8, # 2, p. 331 - 341]

24
[ 5409-31-4 ]
[ 27472-21-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / LiAlH₄ / diethyl ether / a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h 2: SOCl₂, CaCl₂ / benzene / 2 h 3: benzene; H₂O / 6 h / Heating

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

25
[ 5409-31-4 ]
[ 27472-20-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / LiAlH₄ / diethyl ether / a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h 2: SOCl₂, CaCl₂ / benzene / 2 h

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

26
[ 5409-31-4 ]
[ 153742-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 96 percent / LiAlH₄ / diethyl ether / a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h 2: SOCl₂, CaCl₂ / benzene / 2 h 3: benzene; H₂O / 6 h / Heating 4: 1.) NaNH₂ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

27
[ 5409-31-4 ]
[ 153742-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 96 percent / LiAlH₄ / diethyl ether / a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h 2: SOCl₂, CaCl₂ / benzene / 2 h 3: benzene; H₂O / 6 h / Heating 4: 1.) NaNH₂ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h 5: 1.) NaH / 1.) THF, 10 min, 2.) THF, 20 deg C, 3 h

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

28
[ 5409-31-4 ]
[ 153742-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 96 percent / LiAlH₄ / diethyl ether / a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h 2: SOCl₂, CaCl₂ / benzene / 2 h 3: benzene; H₂O / 6 h / Heating 4: 1.) NaNH₂ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h 5: 1.) NaH / 1.) THF, 10 min, 2.) THF, 20 deg C, 3 h 6: 25 percent / HCl

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

29
[ 5409-31-4 ]
(R)-2-(3,4-Diethoxy-phenyl)-2-methyl-malonic acid monomethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 96 percent / LiAlH₄ / diethyl ether / a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h 2: SOCl₂, CaCl₂ / benzene / 2 h 3: benzene; H₂O / 6 h / Heating 4: 1.) NaNH₂ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h 5: 1.) NaH / 1.) THF, 10 min, 2.) THF, 20 deg C, 3 h 6: 25 percent / HCl 7: aq. NaOH (to pH 7.0) / 16 h / 23 °C / pig liver esterase (PLE)

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

30
[ 5409-31-4 ]
(S)-2-(3,4-Diethoxy-phenyl)-2-methyl-malonic acid monomethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 96 percent / LiAlH₄ / diethyl ether / a) 0 deg C to 20 deg C, 1.5 h, b) reflux, 3 h 2: SOCl₂, CaCl₂ / benzene / 2 h 3: benzene; H₂O / 6 h / Heating 4: 1.) NaNH₂ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h 5: 1.) NaH / 1.) THF, 10 min, 2.) THF, 20 deg C, 3 h 6: 25 percent / HCl 7: aq. NaOH (to pH 7.0) / 16 h / 23 °C / pig liver esterase (PLE)

Reference： [1]Provencher; Wynn; Jones; Krawczyk [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026]

31
[ 5409-31-4 ]
[ 42420-04-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / CH₂Cl₂ / 1 h / Heating 2: 83.4 percent / pyridine / 2 h / 0 °C

Reference： [1]Terada; Motomiya; Yoshioka; Narita; Yasui; Takase [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2437 - 2442]

32
[ 5409-31-4 ]
[ 99499-11-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / CH₂Cl₂ / 1 h / Heating 2: 88.2 percent / pyridine / 2 h / 0 °C

Reference： [1]Terada; Motomiya; Yoshioka; Narita; Yasui; Takase [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2437 - 2442]

33
[ 5409-31-4 ]
[ 122892-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / 0.5 h / Heating 2: Et₃N / CHCl₃ / 2 h / Ambient temperature

Reference： [1]Sakaguchi; Nishino; Ogawa; Iwanaga; Yasuda; Kato; Ito [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 202 - 211]

34
[ 5409-31-4 ]
[ 369360-10-1 ]

Yield	Reaction Conditions	Operation in experiment
		N'-((2RS,3R)-3-amino-2-hydroxy-5-(isopropylsulfanyl)pentanoyl)-3,4-diethoxybenzohydrazide N'-((2RS,3R)-3-amino-2-hydroxy-5-(isopropylsulfanyl)pentanoyl)-3,4-diethoxybenzohydrazide The desired compound was prepared by substituting 3,4-diethoxybenzoic acid for o-toluic acid in Example 369. MS(ESI) m/e 414 (M+H)+; 1H NMR (500 MHz, CD3OD) δ 7.51 (m, 1H), 7.48 (m, 1H), 7.02 (m, 1H), 4.47 (d, 0.3H), 4.44 (d, 0.7H), 4.12 (m, 4H), 3.77 (m, 1H), 3.00 (m, 1H), 2.72 (t, 2H), 2.15 (m, 1H), 1.98 (m, 1H), 1.43 (m, 6H), 1.29-1.24 (m, 6H).

Reference： [1]Current Patent Assignee: ABBVIE INC - US2002/2152, 2002, A1

35
[ 79-37-8 ]
[ 5409-31-4 ]
[ 98-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide	e Notes e) The benzoyl chloride was prepared by the dropwise addition of oxalyl chloride (0.75 mmol) to a stirred mixture of 3,4-diethoxybenzoic acid (0.75 mmol) and DMF (a few drops) which had been cooled to 0° C. The mixture was allowed to warm to ambient temperature and was stirred for four hours. The resultant solution was evaporated and the resultant acid chloride was used without further purification. The benzamide product gave the following data: Mass M+H 453.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US6498274, 2002, B1

36
[ 5409-31-4 ]
[ 75-87-6 ]
5-hydroxy-6-ethoxy-3-(trichloromethyl)phthalide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzoic acid In sulfuric acid; water	8 5-Hydroxy-6-ethoxy-3-(trichloromethyl)phthalide EXAMPLE 8 5-Hydroxy-6-ethoxy-3-(trichloromethyl)phthalide To a stirred solution of 16.8 g (80 mmoles) of 3,4-diethoxybenzoic acid in 100 ml. of concentrated sulfuric acid were added dropwise over thirty minutes 16 g (110 mmoles) of chloral. The reaction mixture was stirred at 25° C. for twelve hours. Thin layer chromatographic analysis indicated two components, one of which appeared to be the starting benzoic acid. Six grams of chloral were added to the reaction mixture and stirring was continued for two hours. An additional 10 g of chloral were added and the mixture was stirred for another twelve hours. The reaction mixture was then added to 50 g of ice and 50 g of water, and a solid precipitate formed. The solid product was collected by filtration and then crystallized from ethyl acetate to give 3.3 g of white crystals having a melting point above 260° C. The crystals were dissolved in ethanol and the precipitate which formed was collected, m.p. 143°-144° C. 150 mg. NMR and analysis were consistent for a structure representing 5-hydroxy-6-ethoxy-3-(trichloromethyl)phthalide. Analysis calc. for C11 H9 Cl3 O4: Theory: C, 42.40; H, 2.91; Cl, 34.14. Found: C, 42.45; H, 3.11; Cl, 34.33.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US4333923, 1982, A

37
[ 99-50-3 ]
[ 75-03-6 ]
[ 5409-31-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 3,4-Dihydroxybenzoic acid; ethyl iodide With sodium hydroxide In tetrahydrofuran; water at 0 - 100℃; for 0.0833333h; Stage #2: With hydrogenchloride In water	4 To 30 g of 3,4-Dihydroxybenzoic acid (0.19 mol) in 90 ml of anhydrous tetrahydrofuran was added 225 ml of 4.0 M sodium hydroxide at 0° C. with stirring, followed by adding dropwise 32.7 ml of ethyl iodide (0.409 mol) at 0° C. with stirring. The mixture was stirred for 5 min at room temperature and was heated at 100° C. until TLC did not detect the starting material. After cooling and washing with n-hexane, the solution was acidified to pH 2 with 1N-HCl and washed with ethyl acetate to give 37 g of compound 15 (yield, 90%). 1H-NMR (300 MHz, CDCl3): δ 7.28 (s, 1H), 6.82 (s, 1H), 6.71 (s, 1H), 4.13 (m, 4H), 1.46 (m, 6H).

Reference： [1]Current Patent Assignee: REXAHN PHARMACEUTICALS, INC. - US2005/187231, 2005, A1 Location in patent: Page/Page column 18

38
[ 5409-31-4 ]
[ 133682-08-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With iodine; silver trifluoroacetate In chloroform at 0 - 20℃;

Reference： [1]Location in patent: experimental part Feng, Wei; Satyanarayana, Mavurapu; Cheng, Liang; Liu, Angela; Tsai, Yuan-Chin; Liu, Leroy F.; LaVoie, Edmond J. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 20, p. 9295 - 9301]

39
[ 1372860-36-0 ]
[ 5409-31-4 ]
[ 1201147-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 2h; Stage #2: ethyl 3-{7-[(Z)-(hydroxyimino)(amino)methyl]-1H-indol-3-yl}propanoate In tetrahydrofuran at 60℃; for 2h; Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran at 130℃; for 3h;	D66 Description for D66; Ethyl 3-(7-{5-[3,4-bis(ethyloxy)phenyl]-1 ,2,4-oxadiazol-3-yl}-1 H-indol-3- yl)propanoate (D66); To a solution of 3,4-bis(ethyloxy)benzoic acid (631 mg) in tetrahydrofuran (15 ml.) stirred at room temperature was added EDCI (767 mg) and HOBT (613 mg). The reaction mixture was stirred for 2 h. Then ethyl 3-{7-[(Z)- (hydroxyamino)(imino)methyl]-1 H-indol-3-yl}propanoate (D35) (551 mg) was added. The reaction mixture was stirred at 60 0C for 2 h, and then TBAF (2092 mg) was added. The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 130 0C for 3 h. After cooling the reaction, the solvent was removed. Water (90 ml.) and ethanol (30 ml.) was added to the residue, a yellow solid was formed, filtered and dried in vacuo to afford the product ethyl 3-(7-{5-[3,4- bis(ethyloxy)phenyl]-1 ,2,4-oxadiazol-3-yl}-1 H-indol-3-yl)propanoate (D66) (706 mg). δH (CDCI3, 400 MHz): 1.26 (3H, t), 1.52-1.57 (6H, m), 2.76 (2H, t), 3.18 (2H, t), 4.16 (2H, q), 4.19-4.28 (4H, m), 7.02 (1 H, d), 7.20 (1 H, d), 7.28 (1 H, t), 7.74 (1 H, d), 7.81 (1 H, d), 7.86 (1 H, dd), 8.14 (1 H, dd), 9.64 (1 H, s). MS (ES): C25H27N3O5 requires 449; found 450.2 (M+H+).
	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; Stage #2: ethyl 3-{7-[(Z)-(hydroxyimino)(amino)methyl]-1H-indol-3-yl}propanoate In tetrahydrofuran at 60℃; for 2h; Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran at 130℃; for 3h; Microwave irradiation;	Description for D66; Ethyl 3-(7-{5-[3,4-bis(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate (D66); To a solution of 3,4-bis(ethyloxy)benzoic acid (631 mg) in tetrahydrofuran (15 mL) stirred at room temperature was added EDCI (767 mg) and HOBT (613 mg). The reaction mixture was stirred for 2 h. Then ethyl 3-{7-[(Z)-(hydroxyamino)(imino)methyl]-1H-indol-3-yl}propanoate (D35) (551 mg) was added. The reaction mixture was stirred at 60° C. for 2 h, and then TBAF (2092 mg) was added. The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 130° C. for 3 h. After cooling the reaction, the solvent was removed. Water (90 mL) and ethanol (30 mL) was added to the residue, a yellow solid was formed, filtered and dried in vacuo to afford the product ethyl 3-(7-{5-[3,4-bis(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate (D66) (706 mg). δH (CDCl3, 400 MHz): 1.26 (3H, t), 1.52-1.57 (6H, m), 2.76 (2H, t), 3.18 (2H, t), 4.16 (2H, q), 4.19-4.28 (4H, m), 7.02 (1H, d), 7.20 (1H, d), 7.28 (1H, t), 7.74 (1H, d), 7.81 (1H, d), 7.86 (1H, dd), 8.14 (1H, dd), 9.64 (1H, s). MS (ES): C25H27N3O5 requires 449. found 450.2 (M+H+).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2009/153307, 2009, A1 Location in patent: Page/Page column 69-70
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2010/29729, 2010, A1 Location in patent: Page/Page column 33

40
[ 13257-67-5 ]
[ 5409-31-4 ]
[ 1205602-89-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	1-1.A A. 2-(3,4Diethoxy-benzoylamino)-2-methyl-propionic acid210 mg of 3,4-diethoxybenzoic acid and 160 mg of methyl aminoisobutyrate were stirred in 3 ml of DMF at room temperature. It was treated with 440 mg of HATU and 0.4 ml of DIEA at the same temperature and the reaction was stirred for 2 days. The reaction was monitored by LC-MS, which indicated complete consumption of the starting materials. Product LC-MS (m/z 310.1). This crude reaction mixture was then diluted with 3 ml of water followed by an addition of 250 mg of LiOH. The reaction mixture was stirred at room temperature overnight and the LC-MS analysis indicated the reaction was completed. The reaction mixture was neutralized by 6N-HCl and the resulting creamy precipitates were collected by filtration and washed with water (50 ml). Drying the filter cake yielded the title compound. m/z 296.1 (MH+).

Reference： [1]Current Patent Assignee: CANADA EXPORT; Novartis (w/o Sandoz); NOVARTIS AG - US2010/22513, 2010, A1 Location in patent: Page/Page column 25

41
[ 1220971-95-8 ]
[ 5409-31-4 ]
[ 1220971-96-9 ]

Yield	Reaction Conditions	Operation in experiment
34%	Stage #1: N-hydroxy-2-(hydroxymethyl)benzofuran-5-carboximidamide; 3,4-diethoxybenzoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 40℃; for 0.333333h; Inert atmosphere of N₂; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; dimethyl sulfoxide at 120℃; for 1h;	1.D A mixture of 3,4-diethoxybenzoic acid (0.21 g; 1 mmol), the product of Step C (0.2 g; 0.97 mmol) and hydrochloride salt of 1 -ethyl-3-(3- dimethylaminopropyl) carbodiimide (EDC) (0.22 g; 1.15 mmol) in anhydrous dimethylsulfoxide (DMSO) (2 ml) was stirred for 20 min at ~ 4O0C under N2. To it 1 M tetra-n-butylammonium fluoride (TBAF) in terahydrofuran (THF) (0.4 ml) was added and the resulting mixture was stirred for 1 h at ~ 120 0C, then overnight at room temperature. The solvents were removed in vacuo and the residue was partitioned between EtOAc (15 ml) and H2O (5 ml). The organic phase was washed with brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; CH2CI2) to give the title compound (0.13 g; 34%), as greyish solid. 1H-NMR (CDCI3 ) 8.36 (d, 1 H, J = 3 Hz); 8.09 (dd, 1 H, J = 3, 9 Hz); 7.79 (dd, 1 H, J = 3, 9 Hz); 7.68 (d, 1 H, J = 3 Hz); 7.55 (d, 1 H, J = 9 Hz); 6.98 (d, 1 H, J = 9 Hz); 6.73 (s, 1 H); 4.8 (s, 2H); 4.2 (m, 4H); 2.02 (s, 1 H); 1.51 (m, 6H);
34%	Stage #1: N-hydroxy-2-(hydroxymethyl)benzofuran-5-carboximidamide; 3,4-diethoxybenzoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 40℃; for 0.333333h; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; dimethyl sulfoxide at 20 - 120℃; Inert atmosphere;	1.D Step D: (5-(5-(3,4-Diethoxyphenyl)- 1,2,4-oxadiazol-3-yl)benzofuran-2- yljmethanol: A mixture of 3,4-diethoxybenzoic acid (0.21 g; 1 mmol), the product of Step C (0.2 g; 0.97 mmol) and hydrochloride salt of 1 -ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) (0.22 g; 1 .15 mmol) in anhydrous dimethylsulfoxide (DMSO) (2 ml) was stirred for 20 min at ~ 40°C under N2. To it 1 M tetra-n-butylammonium fluoride (TBAF) in terahydrofuran (THF) (0.4 ml) was added and the resulting mixture was stirred for 1 h at ~ 120 °C, then overnight at room temperature. The solvents were removed in vacuo and the residue was partitioned between EtOAc (15 ml) and H20 (5 ml). The organic phase was washed with brine, dried over anhydrous MgS04 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (Si02; CH2CI2) to give the title compound (0.13 g; 34%), as greyish solid. 1 H- NMR (CDCI3 ) 8.36 (d, 1 H, J = 3 Hz); 8.09 (dd, 1 H, J = 3, 9 Hz); 7.79 (dd, 1 H, J = 3, 9 Hz); 7.68 (d, 1 H, J = 3 Hz) ; 7.55 (d, 1 H, J = 9 Hz); 6.98 (d, 1 H, J = 9 Hz) ; 6.73 (s, 1 H); 4.8 (s, 2H); 4.2 (m, 4H); 2.02 (s, 1 H); 1 .51 (m, 6H) ;

Reference： [1]Current Patent Assignee: AKAAL PHARMA - WO2010/43000, 2010, A1 Location in patent: Page/Page column 46-47
[2]Current Patent Assignee: AKAAL PHARMA - WO2014/63199, 2014, A1 Location in patent: Page/Page column 24; 25

42
[ 1379308-93-6 ]
[ 5409-31-4 ]
[ 1201444-29-2 ]

Yield	Reaction Conditions	Operation in experiment
34%	Stage #1: N-hydroxy-1H-indole-4-carboximidamide; 3,4-diethoxybenzoic acid With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene for 3h; Reflux; Inert atmosphere of N₂;	53.B To a solution of 3,4-diethoxybenzoic acid (0.1 1 g; 0.52 mmol), and the product of Step A (0.09 g; 0.51 mmol) in anhydrous THF (2 ml), PyBroP (0.25 g; 0.54 mmol) was added followed by DIPEA (0.21 ml; 1.22 mmol), with stirring, at room temperature under N2. After 2 h of stirring, the mixture was diluted to 15 ml with EtOAc, washed with saturated NH4CI (2 x 5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was suspended in anhydrous toluene (10 ml). To it 1 M TBAF in THF (0.5 ml) was added and the reaction mixture was refluxed for 3 h under N2, cooled to room temperature and solvents were removed under reduced pressure. The residue was washed with H2O (5 ml) and the solid was purified by FCC (SiO2; CH2CI2) to give the title compound (0.06 g; 34%) as colourless solid. 1H-NMR (CDCI3) 8.42 (s, 1 H); 8.06 (dd, 1 H, J = 2, 8.4 Hz); 7.83 (d, 1 H, J = 8.4Hz); 7.74 (d, 1 H, J = 2 Hz); 7.54 (d, 1 H, J = 8.1 Hz); 7.37 - 7.31 (m, 3H); 6.98 (d, 1 H, J = 8.5 Hz); 4.26 - 4.16 (no, 4H); 1 .5 (m, 6H).
34%	Stage #1: N-hydroxy-1H-indole-4-carboximidamide; 3,4-diethoxybenzoic acid With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 3h; Reflux; Inert atmosphere;	34.B To a solution of 3,4-diethoxybenzoic acid (0.1 1 g; 0.52 mmol), and the product of Step A (0.09 g; 0.51 mmol) in anhydrous THF (2 ml), PyBroP (0.25 g; 0.54 mmol) was added followed by DIPEA (0.21 ml; 1.22 mmol), with stirring, at room temperature under N2. After 2 h of stirring, the mixture was diluted to 15 ml with EtOAc, washed with saturated NH4CI (2 x 5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was suspended in anhydrous toluene (10 ml). To it 1 M TBAF in THF (0.5 ml) was added and the reaction mixture was refluxed for 3 h under N2, cooled to room temperature and solvents were removed under reduced pressure. The residue was washed with H2O (5 ml) and the solid was purified by FCC (SiO2; CH2CI2) to give the title compound (0.06 g; 34%) as colourless solid. 1H-NMR (CDCI3) 1.5 (m, 6H); 4.16 - 4.26 (m, 4H); 6.98 (d, 1 H, J = 8.5 Hz), 7.31 - 7.37 (m, 3H); 7.54 (d, 1 H, J = 8.1 Hz); 7.74 (d, 1 H, J = 2 Hz); 7.83 (d, 1 H, J = 8.4Hz); 8.06 (dd, 1 H, J = 2, 8.4 Hz); 8.42 (s, 1 H).

Reference： [1]Current Patent Assignee: AKAAL PHARMA - WO2010/43000, 2010, A1 Location in patent: Page/Page column 107
[2]Current Patent Assignee: AKAAL PHARMA - WO2010/42998, 2010, A1 Location in patent: Page/Page column 92; 93

43
[ 1221259-73-9 ]
[ 5409-31-4 ]
[ 1221259-74-0 ]

Yield	Reaction Conditions	Operation in experiment
20%	Stage #1: tert-butyl 5-(N-hydroxycarbamimidoyl)isoindoline-2-carboxylate; 3,4-diethoxybenzoic acid With 1,2-dichloro-ethane In N,N-dimethyl-formamide at 60℃; for 1h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; diethylene glycol dimethyl ether at 80℃; for 1h;	65.E A mixture of 3,4-diethoxybenzoic acid (0.19 g; 0.904 mmol), a product of Step D (0.25 g; 0.904 mmol) and EDC (0.27 g; 1 .4 mmol) in anhydrous DMF (2 ml) was stirred at ~ 60 0C for 1 h, then cooled to room temperature and diluted to 20 ml with EtOAc. This was washed with H2O (2 x 5 ml), brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness. The residue was diluted to 3 ml with anhydrous diglyme and 1 M TBAF in THF (0.5 ml) was added and the resulting mixture was stirred at ~ 80 0C for 1 h, then solvents were removed in vacuo. The residue was purified by crystallization from MeOH, to give the title compound (0.084 g; 20%) as greyish solid. 1H-NMR (CDCI3) 1 .4 - 1.6 (m, 15H + H2O); 4.14 - 4.24 (m, 4H); 4.7 - 4.76 (m, 4H); 6.97 (d, 1 H, J = 6 Hz); 7.32 - 7.4 (m, 1 H); 7.66 (d, 1 H, J = 3 Hz); 7.78 (dd, 1 H, J = 3, 9 Hz); 8.02 - 8.08 (m, 2H).

Reference： [1]Current Patent Assignee: AKAAL PHARMA - WO2010/42998, 2010, A1 Location in patent: Page/Page column 140

44
[ 1379294-98-0 ]
[ 5409-31-4 ]
[ 1201445-09-1 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: N-hydroxy-1H-indole-5-carboximidamide; 3,4-diethoxybenzoic acid With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In toluene for 1h; Reflux; Inert atmosphere;	40.A To a solution of 3,4-diethoxybenzoic acid (0.1 1 g; 0.52 mmol), and the product of Example 7, Step C (0.09 g; 10.52 mmol) in anhydrous THF (2 ml), PyBroP (0.25 g; 0.53 mmol) was added, followed by DIPEA (0.21 ml; 1 .2 mmol), with stirring, at room temperature under N2. After overnight stirring, the mixture was diluted to 15 ml with EtOAc, washed with saturated NH4CI (3 x 5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2, EtOAc) to give the coupling product. This was suspended in anhydrous toluene (3ml) and 1 M TBAF was added. The resulting mixture was refluxed for 1 h under N2, cooled to room temperature and diluted to 15 ml with EtOAc, washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness. The residue was purified by crystallization from MeOH, to give the title compound (0.096 g; 53%), as a colourless solid. . 1H-NMR (CDCI3) 1 .5 (m, 6H); 4.19 (m, 4H); 6.66 (s, 1 H); 6.98 (d, 1 H, J = 8.4 Hz); 7.26 (m, 1 H); 7.47 (d, 1 H, J = 8.5 Hz); 7.71 (d, 1 H, J = 1.8 Hz); 7.8 (dd, 1 H, J = 1.8, 8.5 Hz); 8.0 (dd, 1 H, J = 1.3, 8.5 Hz); 8.37 (broad s, 1 H); 8.5 (s, 1 H).

Reference： [1]Current Patent Assignee: AKAAL PHARMA - WO2010/42998, 2010, A1 Location in patent: Page/Page column 101

45
[ 1035218-16-6 ]
[ 5409-31-4 ]
[ 1201444-29-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: N'-hydroxy-1H-indole-4-carboximidamide In N,N-dimethyl-formamide at 20 - 95℃; for 14.5h;	2-(4-(5-(3,4-diethoxyphenyl)-l,2,4-oxadiazol-3-yl)indolin-l-yl)ethanolTo a stirred solution of 3,4-diethoxybenzoic acid (400mg, 1.9mmol) in DMF were added sequentially HOBt (330mg, 2.5 mmol) and EDCI (474mg, 2.5mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of the iV -hydroxy- lH-indole-4-carboximidamide (666mg, 3.8mmol). The reaction was stirred for additional 30 min at room temperature then heated at 90-95 °C for 14h. The reaction was cooled to room temperature, diluted using a saturated solution OfNa2CO3 and extracted with EtOAc (100ml X3). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:Me0H (9:1) to afford compound 110 in 50% yield (331mg). H1 NMR (400 MHz, CDCl3): J8.01 (d, J= 7.2 Hz, IH), 7.81 (dd, Jl = 2.0 Hz, J2 = 8.4 Hz, IH), 7.52 (s, IH), 7.52 (d, J= 8.0 Hz, IH), 7.34 (s, IH), 7.28 (t, J= 8.0 Hz, IH), 7.23 (s, IH), 6.96 (d, J= 8.4 Hz, IH), 4.18 (q, J = 6.8 Hz, 2H), 4.16 (q, J= 6.8 Hz, 2H), 1.47 (t, J= 6.8 Hz, 3H), 1.46 (t, J= 6.8 Hz, 3H); 13C NMR (I OO MHZ, CDCl3): «5175.0, 169.5, 152.6, 148.9 (2), 125.7, 122.2, 121.8, 121.7, 121.3, 121.2, 117.0, 114.4, 114.3, 112.7, 112.5, 64.97, 64.76, 14.86, 14.78. MS (EI) m/z 350 (M+), HRMS (EI) for C20H19N3O3 (M+): calcd 350.1499, found 350.1504.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1 Location in patent: Page/Page column 159-160

46
[ 952511-29-4 ]
[ 5409-31-4 ]
[ 1201445-36-4 ]

Yield	Reaction Conditions	Operation in experiment
5%	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: N-hydroxy-1H-pyrrolo[2,3-b]pyridine-4-carboximidamide In N,N-dimethyl-formamide at 20 - 95℃; for 16.5h;	5-(3,4-diethoxyphenyl)-3-(lH-pyrroIo[2,3-b]pyridin-4-yl)-l,2,4-oxadiazoleTo a solution of 4-cyano-7-azaindole (Ig, 7 mmol) in methanol (30 mL) were added cautiously hydroxylamine hydrochloride (632 mg, 9.1 mmol) and sodium carbonate (964mg, 9.1 mmol). The reaction mixture was reflux for 6h under nitrogen atmosphere and hydroxylamine hydrochloride (632 mg, 9.1 mmol) and sodium carbonate (964mg, 9.1 mmol) were added, the reaction was reflux for additional 14h. The mixture was cooled to room temperature and the solid was filtered. The organic solvent was concentrated under reduced pressure and the crude was recrystallized from ethanol to yield 200mg of JV- hydroxyimidamide. To a stirred solution of 3,4-diethoxybenzoic acid (50mg, 0.24 mmol) inDMF was added EDCI (59 mg, 0.31 mmol) and HOBt (41 mg, 0.31 mmol), the reaction was stirred 20 min at room temperature. To the reaction was added the N-hydroxyimidamide (54mg, 0.31 mmol) and the mixture was stirred for 30 min at room temperature followed by 16h at 95 °C. The reaction was concentrated under reduced pressure, diluted with EtOAc (80 ml) and washed with a saturated solution OfNaHCO3 (2X30ml) and brine (50ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by column chromatography using CH2Cl2--MeOH (9:1) to offer the product as a brown solid in 5% yield (4mg, 0.01 mmol). MS (EI) m/z: 351 (M+)

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1 Location in patent: Page/Page column 154

47
[ 1201448-08-9 ]
[ 5409-31-4 ]
[ 1201446-08-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: N'-hydroxy-2-(hydroxymethyl)pyridine-4-carboxamidine In N,N-dimethyl-formamide at 20 - 130℃; for 1.08333h; Microwave irradiation;	In a microwave vial, a stirring solution of 3,4-diethoxybenzoic acid(300mg, 1.43mmol) in DMF was treated with HOBt (250 mg, 1.85mmol) and EDCI (354mg, 1.85mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of amidoxime (309mg, 1.85mmol). The reaction was stirred for additional 30 min at room temperature and then heated to 130 0C for 35 min in the initiator. The reaction was diluted using a saturated solution of NaCl and extracted with EtOAc (3X80ml). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:Me0H (9:1) to offer (4-(5-(3,4-diethoxyphenyl)-l,2,4-oxadiazol-3- yl)pyridin-2-yl)methanol as brown solid in 71% yield (350mg). 1H NMR (400 MHz, CDCl3): δ 8.65 (d, J= 4.8 Hz, IH), 8.00 (s, IH), 7.86 (d, J= 4.8 Hz, IH), 7.70 (dd, J7 = 2.0 Hz, J2 = 8.8 Hz, IH), 7.59 (d, J= 2.0, IH), 6.91 (d, J= 8.8 Hz, IH), 4.85 (s, 2H), 4.16 (q, J= 7.2 Hz, 2H), 4.13 (q, J =7.2 Hz, 2H), 1.49 (t, J = 6.8 Hz, 3H), 1.46 (t, J= 6.8 Hz, 3H); 13C NMR (100 MHz CDCl3): δ 176.54, 167.22, 153.03, 149.36, 148.91, 135.50, 122.23, 120.11, 118.48, 116.05, 112.48, 112.17, 64.90, 64.50, 14.82, 14.73. MS (EI) m/z: 342 (M+), HRMS (EI) for C18H19N3CK

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1 Location in patent: Page/Page column 158-159

48
C₉H₉N₃O₂ [ No CAS ]
[ 5409-31-4 ]
[ 1201445-13-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,4-dioxane at 20℃; for 0.333333h; Stage #2: C₉H₉N₃O₂ In 1,4-dioxane at 20 - 95℃; for 16.5h;	6-(5-(3,4-diethoxyphenyl)-l,2,4-oxadiazol-3-yl)indolin-2-oneTo a solution of 2-oxoindoline-4-carbonitrile (500mg, 3.16mmol) in ethanol were added cautiously hydroxylamine hydrochloride (286 mg, 4.11 mmol) and potassium bicarbonate (41 lmg, 4.11 mmol). The reaction mixture was refluxed for 2Oh under nitrogen atmosphere. The mixture was cooled to room temperature and the solid was filtered. The organic solvent was concentrated under reduced pressure and the iV-hydroxyimidamide was used in the next step without further purification.To a stirred solution of 3,4-diethoxybenzoic acid (73mg, 0.35 mmol) in 1,4-dioxane was added EDCI (87 mg, 0.45 mmol) and HOBt (62 mg, 0.45 mmol), the reaction was stirred 20 min at room temperature. To the reaction was added the 7V-hydroxyimidamide (87mg, 0.45 mmol) and the mixture was stirred for 30 min at room temperature followed by 16h at 95 0C. The reaction was concentrated under reduced pressure, diluted with EtOAc (80 ml) and washed with brine (2X30ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by column chromatography using CH2Cl2:Me0H (9:1) to offer the product as a pale yellow solid 50% yield (64mg, 0.175 mmol). MS (EI) m/z: 366 (M+)

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1 Location in patent: Page/Page column 153-154

49
[ 1093827-51-0 ]
[ 5409-31-4 ]
[ 1093827-52-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: N',1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide In N,N-dimethyl-formamide at 20 - 130℃; for 1.08333h; Microwave irradiation;	To a stirred solution of l-hydroxy-2,3-dihydro-l//-indene-4-carbonitrile (3g, 18.86 mmol) in ethanol (100 mL) were added cautiously over a period of 16h under refluxing conditions hydroxylamine hydrochloride (6.55g, 94.3 mmol) and potassium carbonate (13.03g, 94.3 mmol) in equal portions. The mixture was cooled to room temperature and the solid was filtered. The organic solvent was concentrated under reduced pressure and the crude was recrystallized from ethanol to yield 2.5g (69%) of amidoxime.In a microwave vial, a stirring solution of 3,4-diethoxybenzoic acid (200mg, 0.95mmol) in DMF was treated with HOBt (168 mg, 1.24mmol) and EDCI (237mg, 1.24mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of amidoxime (238mg, 1.24mmol). The reaction was stirred for additional 30 min at room temperature and then heated to 130 °C for 35 min in the initiator. The reaction was diluted using a saturated solution of NaCl and extracted with EtOAc (3X80ml). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (9:1) to offer the product as a white solid in 69% yield (208mg). 1H NMR (400 MHz, CDCl3): «58.10 (d, J= 7.6, IH), 7.78 (dd, Jl = 1.6 Hz, J2 = 8 Hz, IH), 7.67 (d, J= 1.6 Hz, IH), 7.56 (d, J= 7.6 Hz, IH), 7.39 (t, J= 7.6 Hz, IH), 6.97 (d, J= 8.0 Hz, IH), 5.29 (t, J= 6.4 Hz, IH), 4.19 (q, J= 7.2 Hz, 2H), 4.18 (q, J= 7.2 Hz, 2H), 3.51-4.43 (m, IH), 3.22-3.14 (m, IH), 2.59-2.51 (m, IH), 2.04- 1.97 (m, IH), 1.5 (t, J= 7.2 Hz, 3H), 1.49 (t, J= 7.2, 3H); 13C NMR (100 MHz, CDCl3): «5175.2, 168.9, 152.8, 148.9, 146.6, 143.3, 128.9, 127.4, 127.0, 123.8, 122.2, 116.7, 112.7, 112.4, 76.2, 64.9, 64.8, 35.7, 31.5, 14.9, 14.8. MS (EI) m/z 367 (M+), HRMS (EI) for C2,H22N2O4 (M+): calcd 367.1652, found 367.1653.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1 Location in patent: Page/Page column 157-158

50
[ 5409-31-4 ]
[ 1201444-53-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.33 h / 20 °C 1.2: 14.5 h / 20 - 95 °C 2.1: sodium cyanoborohydride; acetic acid / 10 - 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1

51
[ 5409-31-4 ]
[ 1201446-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.33 h / 20 °C 1.2: 14.5 h / 20 - 95 °C 2.1: sodium cyanoborohydride; acetic acid / 10 - 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 60 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; THE SCRIPPS RES INSTITTUTE - WO2009/151529, 2009, A1

52
[ 5409-31-4 ]
[ 1349175-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / 3 h / 90 °C 2.1: sodium hydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 24 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Bland, Nicholas D.; Wang, Cuihua; Tallman, Craig; Gustafson, Alden E.; Wang, Zhouxi; Ashton, Trent D.; Ochiana, Stefan O.; McAllister, Gregory; Cotter, Kristina; Fang, Anna P.; Gechijian, Lara; Garceau, Norman; Gangurde, Rajiv; Ortenberg, Ron; Ondrechen, Mary Jo; Campbell, Robert K.; Pollastri, Michael P. [Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8188 - 8194]

53
[ 64-17-5 ]
[ 5409-31-4 ]
[ 75332-44-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sulfuric acid In benzene for 12h; Reflux;
85%	With sulfuric acid Reflux;	General method for the preparation of esters 64-65 General procedure: The appropriate acid 62 or 63 (1 eq) was suspended in EtOH (2.12 mlmmol/eq) and H2SO4 (0.1 mlmmol/eq) was added to the mixture. The reaction was refluxed over night, then cooled to r.t. and dried under vacuum. The residue was partitioned between sat.aq. NaHCO3 solution (30 ml) and EtOAc (3x35 ml). The combined organic extracts was washed with sat.aq. NaHCO3 solution (20 ml) and water (20 ml), dried over MgSO4 and concentrated in vacuum to give the pure title compounds.

Reference： [1]Location in patent: experimental part Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]
[2]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]

54
[ 5409-31-4 ]
[ 1351800-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

55
[ 5409-31-4 ]
[ 1351800-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

56
[ 5409-31-4 ]
[ 1351800-48-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere 4: methanesulfonic acid / dichloromethane / 1 h / 20 °C

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

57
[ 5409-31-4 ]
[ 1351800-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere 4: methanesulfonic acid / dichloromethane / 1 h / 20 °C 5: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

58
[ 5409-31-4 ]
[ 1351800-53-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere 4: methanesulfonic acid / dichloromethane / 1 h / 20 °C 5: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 6: sodium azide / trifluoroacetic acid / 12 h / 20 °C

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

59
[ 5409-31-4 ]
[ 1351800-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere 4: methanesulfonic acid / dichloromethane / 1 h / 20 °C 5: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 6: sodium azide / trifluoroacetic acid / 12 h / 20 °C 7: Raney-Ni / isopropyl alcohol / 12 h / Inert atmosphere; Reflux

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

60
[ 5409-31-4 ]
[ 1351800-62-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere 4: methanesulfonic acid / dichloromethane / 1 h / 20 °C 5: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 6: sodium azide / trifluoroacetic acid / 12 h / 20 °C 7: Raney-Ni / isopropyl alcohol / 12 h / Inert atmosphere; Reflux 8: tetrahydrofuran / 12 h / 20 °C

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

61
[ 5409-31-4 ]
[ 1351800-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

62
[ 5409-31-4 ]
[ 1351800-68-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sulfuric acid / benzene / 12 h / Reflux 2: bromine / acetic acid / 36 h / 35 °C 3: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere 4: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux
	Multi-step reaction with 5 steps 1.1: sulfuric acid / benzene / 12 h / Reflux 2.1: bromine / acetic acid / 36 h / 35 °C 3.1: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 4.1: tetrahydrofuran / 0.5 h / -5 - 0 °C / Inert atmosphere 5.1: sodium hydroxide / ethanol; water / Reflux 5.2: pH 2

Reference： [1]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]
[2]Miao, Hua-Ming; Zhao, Gui-Long; Zhang, Lin-Shan; Shao, Hua; Wang, Jian-Wu [Helvetica Chimica Acta, 2011, vol. 94, # 11, p. 1981 - 1993]

63
C₉H₁₄O₃ [ No CAS ]
[ 5409-31-4 ]
[ 1393674-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere;	Step 2: General procedure: To a solution of the alcohol (1 equiv) in dried THF at 0 °C under a nitrogen atmosphere was added the acid (1.5 equiv) and triphenylphosphine (1.7 equiv), respectively. Then diisopropyl azodicarboxylate (1.7 equiv) was added slowly. The reaction mixture was stirred overnight, quenched with saturated NaHCO3, concentrated, and extracted with ethyl acetate for three times. The combined organic phase was dried over Na2SO4, concentrated, and the residue was purified with column chromatography to give the substrate in 60-85% yield.

Reference： [1]Xing, Xiangyou; Zhao, Yaohong; Xu, Chen; Zhao, Xinyang; Wang, David Zhigang [Tetrahedron, 2012, vol. 68, # 36, p. 7288 - 7294]

64
[ 355817-01-5 ]
[ 5409-31-4 ]
[ 1414864-31-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: C₁₅H₁₂ClNO₃; 3,4-diethoxybenzoic acid With thionyl chloride Stage #2: With triethylamine In tetrahydrofuran

Reference： [1]Chen, Yingyi; Wen, Donghua; Huang, Zhimin; Huang, Min; Luo, Yu; Liu, Bin; Wu, Yingli; Zhang, Jian; Lu, Han; Peng, Yuefeng [Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 22, p. 6867 - 6870,4]

65
[ 123-91-1 ]
[ 5409-31-4 ]
[ 1597710-72-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With iron(III)-acetylacetonate; di-tert-butyl peroxide at 120℃; for 24h; Schlenk technique;

Reference： [1]Zhao, Jincan; Fang, Hong; Zhou, Wei; Han, Jianlin; Pan, Yi [Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 3847 - 3855]

66
[ 5409-31-4 ]
[ 1608146-68-4 ]
[ 1608146-70-8 ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: 3,4-diethoxybenzoic acid; N,6-dihydroxy-5-iodonicotinimidamide With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 40℃; for 2h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; dimethyl sulfoxide at 110℃; for 3h; Inert atmosphere;	32.F Step F: 5-(5-(3,4-Diethoxyphenyl)-1,2 -oxadiazol-3-yl)-3-iodopyridin-2-ol: A mixture of the product of Step E (0.31 g, 1 .1 mol) 3,4-dietoxybenzoic acid (0.24 g, 1 .1 mmol) and EDC (0.32 g, 1 .67 mmol) in anhydrous DMSO (1 .5 ml) was stirred for 2 h at ~ 40°C. To it 1 M TBAF in THF (0.5 ml) and the mixture was degassed in vacuo and saturated with N2, than stirred for 1 h at ~ 1 10oC. A fresh portion of 1 M TBAF (0.5 ml) was added and stirring was continued for 2 more h and the mixture was cooled to room temperature. This was partitioned between EtOAc (150 ml and H20 (20 ml). The organic phase was washed with brine, dried over anhydrous MgS04, filtered and the filtrate evaporated under reduced pressure and the residue was purified by FCC (Si02, CH2CI2/EtOAc 1 /1 ) to give the title compound (0.161 g, 25%), as colourless solid. 1 H NMR (DMSO-d6) 8.49 (s, 1 H), 8.09 (s, 1 H), 7.69 (d, 1 H, J = 6 Hz), 7,55 (s, 1 H), 7.13 (d, 1 H, J = 6 Hz), 4.1 1 (broad s, 4H), 1 .33 (broad s, 6H

Reference： [1]Current Patent Assignee: AKAAL PHARMA - WO2014/63199, 2014, A1 Location in patent: Page/Page column 59; 60

67
[ 5409-31-4 ]
[ 1477751-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / 80 °C 2: potassium carbonate / ethyl acetate / 0 °C

Reference： [1]Fang, Fei; Li, Dong-Dong; Li, Jing-Ran; Sun, Jian; Du, Qian-Ru; Gong, Hai-Bin; Zhu, Hai-Liang [RSC Advances, 2013, vol. 3, # 48, p. 26230 - 26240]

68
[ 5409-31-4 ]
2-amino-N-(2-(dimethylamino)ethyl)-3-(3′-(trifluoromethyl)biphenyl-4-yl)propanamide hydrochloride [ No CAS ]
[ 76-05-1 ]
N-(1-(2-(dimethylamino)ethylamino)-1-oxo-3-(3'-(trifluoromethyl)biphenyl-4-yl)propan-2-yl)-3,4-diethoxybenzamide trifluoroacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.2%	Stage #1: 3,4-diethoxybenzoic acid; 2-amino-N-(2-(dimethylamino)ethyl)-3-(3′-(trifluoromethyl)biphenyl-4-yl)propanamide hydrochloride With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 18 - 30℃; for 2h; Stage #2: trifluoroacetic acid In water; acetonitrile

Reference： [1]Yang, Bin; Lamb, Michelle L.; Zhang, Tao; Hennessy, Edward J.; Grewal, Gurmit; Sha, Li; Zambrowski, Mark; Block, Michael H.; Dowling, James E.; Su, Nancy; Wu, Jiaquan; Deegan, Tracy; Mikule, Keith; Wang, Wenxian; Kaspera, Rüdiger; Chuaqui, Claudio; Chen, Huawei [Journal of Medicinal Chemistry, 2014, vol. 57, # 23, p. 9958 - 9970]

69
[ 5409-31-4 ]
2-((1E,3E)-5-((E)-1-(3-aminopropyl)-3,3-dimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-1-(3-((tert-butoxycarbonyl)amino)propyl)-3,3-dimethyl-3H-indol-1-ium acetate [ No CAS ]
C₄₇H₆₁N₄O₅⁽¹⁺⁾*C₂H₃O₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃;

Reference： [1]Zhang, Liyun; Er, Jun Cheng; Li, Xin; Heng, Jun Jie; Samanta, Animesh; Chang, Young-Tae; Lee, Chi-Lik Ken [Chemical Communications, 2015, vol. 51, # 34, p. 7386 - 7389]

70
[ 55919-73-8 ]
[ 5409-31-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With water; sodium hydroxide In ethanol at 60℃; for 1.5h;	24.2 Step 2: 3, 4-Diethoxybenzoic acid Step 2: 3, 4-Diethoxybenzoic acid[0794]To a 100 mL two-necked flask were added methyl 3, 4-diethoxybenzoate (2.0 g, 8.92 mmol) , sodium hydroxide (1.79 g, 44.64 mmol) , ethanol (30 mL) and water (15 mL) . The mixture was stirred at 60 for 1.5 hours and concentrated to remove ethanol. To the residue was added hydrochloric acid (1 M) to adjust the pH of the mixuture to 1. The mixture was extracted with ethyl acetate (50 mL × 3) . The organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was removed to give the title compound as a white solid (1.85 g, 99) .[0795]1H NMR (400 MHz, CDCl3) : δ ppm 10.95 (br. s, 1H) , 7.73 (d, J 8.4 Hz, 1H) , 7.59 (s, 1H ) , 6.89 (d, J 8.4 Hz, 1H) , 4.17 -4.14 (m, 4H) , 1.50 -1.45 (m, 6H) and MS-ESI: m/z 211.1 [M+H]+.

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2015/161830, 2015, A1 Location in patent: Paragraph 00366

71
[ 5409-31-4 ]
[ 5680-79-5 ]
[ 405148-75-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: glycine ethyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 12h;	24.3 Step 3: Methyl 2- (3, 4-diethoxybenzamido) acetate Step 3: Methyl 2- (3, 4-diethoxybenzamido) acetate[0797]To 80 mL of dichloromethane were added 3, 4-diethoxybenzoic acid (6.37 g, 30.3 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (8.72 g, 45.5 mmol) and 1-hydroxybenzotriazole (6.15 g, 45.5 mmol) . The mixture was stirred at rt for 30 minutes, then glycine methyl ester hydrochloride (4.57 g, 36.4 mmol) and N, N-diisoproylethylamine (15.9 mL, 91.0 mmol) were added at 0 . The resulting mixture was stirred at rt for 12 hours. The reaction mixture was washed with water (40 mL × 3) . The organic layer was dried over anhydrous sodium sulfate and concentrated, then the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 1/1) to give the title compound as a white solid (6.73 g, 79) .[0798]1H NMR (400 MHz, CDCl3) : δ ppm 7.41 (s, 1H) , 7.31 (d, J 8.3 Hz, 1H) , 6.84 (d, J 8.3 Hz, 1H ) , 6.72 (br. s, 1H) , 4.19 (s, 2H) , 4.14 -4.08 (m, 4H) , 3.77 (s, 3H) , 1.46 -1.41 (m, 6H) and MS-ESI: m/z 282.1 [M+H]+.

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2015/161830, 2015, A1 Location in patent: Paragraph 00367

72
[ 1762-34-1 ]
[ 5409-31-4 ]
Tb₇O₄ [ No CAS ]
[Tb(3,4-diethoxybenzoic acid)5,5'-dimethyl-2,2'-bipyridine]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Tb₇O₄ With hydrogenchloride In water Stage #2: 5,5'-dimethyl-2,2'-bipyridine; 3,4-diethoxybenzoic acid With sodium hydroxide In ethanol for 18h;	Preparation of the compounds General procedure: A mixture of 3,4,-DEOHBA (0.6 mmol) and 5,50-DME-2,20-BIPY (0.2 mmol) was dissolved in an ethanol solution(95 %), adjusting the pH of the solution to 5.8-6.2 with aNaOH solution (1 mol/L) Then, the resulting solution wasadded dropwise into the aqueous solution of LnCl36H2O(0.2 mmol) under stirring. After stirring for 6 h anddepositing for 12 h, the precipitates were filtered and dried[13]. And the mother liquor was evaporated slowly. Thesingle crystal of complex 1 was collected after 2 weeks.Element analysis (%): complex 1 [Tb(3,4-DEOBA)35,50-DME-2,20-BIPY]2 calcd: C, 55.67; H, 5.295; N, 2.886; Tb,16.37. Found: C, 54.54; H, 5.387; N, 2.758; Tb, 15.97.Complex 2 [Dy(3,4,-DEOBA)35,50-DME-2,20- BIPY]2Calcd for 2: C, 55.47; H, 5.276; N, 2.875; Dy, 16.68.Found: C, 54.83; H, 5.404; N, 2.863; Dy, 16.46;

Reference： [1]Jin, Cheng-Wei; Shen, Pan-Pan; Ren, Ning; Geng, Li-Na; Zhang, Jian-Jun [Journal of Thermal Analysis and Calorimetry, 2016, vol. 126, # 3, p. 1549 - 1558]

73
dysprosium((III) oxide [ No CAS ]
[ 1762-34-1 ]
[ 5409-31-4 ]
[Dy(3,4-diethoxybenzoic acid)5,5'-dimethyl-2,2'-bipyridine]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: dysprosium((III) oxide With hydrogenchloride In water Stage #2: 5,5'-dimethyl-2,2'-bipyridine; 3,4-diethoxybenzoic acid With sodium hydroxide In ethanol for 18h;	Preparation of the compounds General procedure: A mixture of 3,4,-DEOHBA (0.6 mmol) and 5,50-DME-2,20-BIPY (0.2 mmol) was dissolved in an ethanol solution(95 %), adjusting the pH of the solution to 5.8-6.2 with aNaOH solution (1 mol/L) Then, the resulting solution wasadded dropwise into the aqueous solution of LnCl36H2O(0.2 mmol) under stirring. After stirring for 6 h anddepositing for 12 h, the precipitates were filtered and dried[13]. And the mother liquor was evaporated slowly. Thesingle crystal of complex 1 was collected after 2 weeks.Element analysis (%): complex 1 [Tb(3,4-DEOBA)35,50-DME-2,20-BIPY]2 calcd: C, 55.67; H, 5.295; N, 2.886; Tb,16.37. Found: C, 54.54; H, 5.387; N, 2.758; Tb, 15.97.Complex 2 [Dy(3,4,-DEOBA)35,50-DME-2,20- BIPY]2Calcd for 2: C, 55.47; H, 5.276; N, 2.875; Dy, 16.68.Found: C, 54.83; H, 5.404; N, 2.863; Dy, 16.46;

Reference： [1]Jin, Cheng-Wei; Shen, Pan-Pan; Ren, Ning; Geng, Li-Na; Zhang, Jian-Jun [Journal of Thermal Analysis and Calorimetry, 2016, vol. 126, # 3, p. 1549 - 1558]

74
[ 1762-34-1 ]
dysprosium(III) chloride hexahydrate [ No CAS ]
[ 5409-31-4 ]
[Dy(3,4-diethoxybenzoic acid)5,5'-dimethyl-2,2'-bipyridine]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol for 18h;	Preparation of the compounds General procedure: A mixture of 3,4,-DEOHBA (0.6 mmol) and 5,50-DME-2,20-BIPY (0.2 mmol) was dissolved in an ethanol solution(95 %), adjusting the pH of the solution to 5.8-6.2 with aNaOH solution (1 mol/L) Then, the resulting solution wasadded dropwise into the aqueous solution of LnCl36H2O(0.2 mmol) under stirring. After stirring for 6 h anddepositing for 12 h, the precipitates were filtered and dried[13]. And the mother liquor was evaporated slowly. Thesingle crystal of complex 1 was collected after 2 weeks.Element analysis (%): complex 1 [Tb(3,4-DEOBA)35,50-DME-2,20-BIPY]2 calcd: C, 55.67; H, 5.295; N, 2.886; Tb,16.37. Found: C, 54.54; H, 5.387; N, 2.758; Tb, 15.97.Complex 2 [Dy(3,4,-DEOBA)35,50-DME-2,20- BIPY]2Calcd for 2: C, 55.47; H, 5.276; N, 2.875; Dy, 16.68.Found: C, 54.83; H, 5.404; N, 2.863; Dy, 16.46;

Reference： [1]Jin, Cheng-Wei; Shen, Pan-Pan; Ren, Ning; Geng, Li-Na; Zhang, Jian-Jun [Journal of Thermal Analysis and Calorimetry, 2016, vol. 126, # 3, p. 1549 - 1558]

75
[ 1762-34-1 ]
terbium(III) chloride hexahydrate [ No CAS ]
[ 5409-31-4 ]
[Tb(3,4-diethoxybenzoic acid)5,5'-dimethyl-2,2'-bipyridine]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol for 18h;	Preparation of the compounds General procedure: A mixture of 3,4,-DEOHBA (0.6 mmol) and 5,50-DME-2,20-BIPY (0.2 mmol) was dissolved in an ethanol solution(95 %), adjusting the pH of the solution to 5.8-6.2 with aNaOH solution (1 mol/L) Then, the resulting solution wasadded dropwise into the aqueous solution of LnCl36H2O(0.2 mmol) under stirring. After stirring for 6 h anddepositing for 12 h, the precipitates were filtered and dried[13]. And the mother liquor was evaporated slowly. Thesingle crystal of complex 1 was collected after 2 weeks.Element analysis (%): complex 1 [Tb(3,4-DEOBA)35,50-DME-2,20-BIPY]2 calcd: C, 55.67; H, 5.295; N, 2.886; Tb,16.37. Found: C, 54.54; H, 5.387; N, 2.758; Tb, 15.97.Complex 2 [Dy(3,4,-DEOBA)35,50-DME-2,20- BIPY]2Calcd for 2: C, 55.47; H, 5.276; N, 2.875; Dy, 16.68.Found: C, 54.83; H, 5.404; N, 2.863; Dy, 16.46;

Reference： [1]Jin, Cheng-Wei; Shen, Pan-Pan; Ren, Ning; Geng, Li-Na; Zhang, Jian-Jun [Journal of Thermal Analysis and Calorimetry, 2016, vol. 126, # 3, p. 1549 - 1558]

76
[ 5409-31-4 ]
(4S,5R)-tert-butyl 4-((2,6-dichloro-4-(hydrazinecarbonyl)phenoxy)methyl)-2,2,5-trimethyloxazolidine-3-carboxylate [ No CAS ]
C₃₀H₃₉Cl₂N₃O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,4-diethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 2h; Stage #2: (4S,5R)-tert-butyl 4-((2,6-dichloro-4-(hydrazinecarbonyl)phenoxy)methyl)-2,2,5-trimethyloxazolidine-3-carboxylate In N,N-dimethyl-formamide for 17h;	24 To a soln of 3,4-diethoxy-benzoic acid (100 mg, 0.476 mmol) in DMF (4.0 mL) were added EDCI (1 15 mg, 0.600 mmol) and HOBt (81 mg, 0.60 mmol). After 2 h, compound I- 112 (200 mg, 0.446 mmol) was added. After 17 h, the rxn was quenched with sat'd NaHC03 aq soln (15 mL). The mixture was extracted with ethyl acetate (2x20 mL). The combined organics were washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified via Combi-flash column on silica gel (0-40% ethyl acetate in heptanes) to afford compound 1-113.

Reference： [1]Current Patent Assignee: EXELIXIS INC - WO2017/4609, 2017, A1 Location in patent: Paragraph 0331

77
20'-aminovinblastine [ No CAS ]
[ 5409-31-4 ]
C₅₇H₇₁N₅O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 23℃; for 12h; Inert atmosphere;

Reference： [1]Lukesh, John C.; Carney, Daniel W.; Dong, Huijun; Cross, R. Matthew; Shukla, Vyom; Duncan, Katharine K.; Yang, Shouliang; Brody, Daniel M.; Brütsch, Manuela M.; Radakovic, Aleksandar; Boger, Dale L. [Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7591 - 7604]

78
[ 5409-31-4 ]
3-(4-(tert-butyl)phenyl)propanehydrazide [ No CAS ]
2-(4-(tert-butyl)phenethyl)-5-(3,4-diethoxyphenyl)-1,3,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With trichlorophosphate Reflux;	General procedure for the synthesis of substituted di-aryl oxazoles 71-72, 77-80, 88-89 General procedure: A mixture of the appropriate hydrazide 66-67, 75-76 or 87 (1 eq,) and the appropriate carboxylic acid 31 or 62-63 (1 eq) in POCl3 (8.5 mlmmol/eq) was heated under reflux over night. The excess POCl3 was removed under reduced pressure, then the residue was poured onto ice. The mixture was extracted with EtOAc (30 mlmmol/eq) and NaHCO3 (25 ml*mmol/eq). The organic layer was dried over MgSO4 and concentrated in vacuum. The crude residue was purified by flash column chromatogaphy to give the pure title compounds.

Reference： [1]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]

79
[ 3538-68-9 ]
[ 5409-31-4 ]
2-(3,4-diethoxyphenyl)-5-phenethyl-1,3,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With trichlorophosphate;Reflux;	General procedure: A mixture of the appropriate hydrazide 66-67, 75-76 or 87 (1 eq,) and the appropriate carboxylic acid 31 or 62-63 (1 eq) in POCl3 (8.5 mlmmol/eq) was heated under reflux over night. The excess POCl3 was removed under reduced pressure, then the residue was poured onto ice. The mixture was extracted with EtOAc (30 mlmmol/eq) and NaHCO3 (25 ml*mmol/eq). The organic layer was dried over MgSO4 and concentrated in vacuum. The crude residue was purified by flash column chromatogaphy to give the pure title compounds.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 56 - 68

80
2-(4-(tert-butyl)phenyl)acetohydrazide [ No CAS ]
[ 5409-31-4 ]
2-(4-(tert-butyl)benzyl)-5-(3,4-diethoxyphenyl)-1,3,4,-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With trichlorophosphate Reflux;	General procedure for the synthesis of substituted di-aryl oxazoles 71-72, 77-80, 88-89 General procedure: A mixture of the appropriate hydrazide 66-67, 75-76 or 87 (1 eq,) and the appropriate carboxylic acid 31 or 62-63 (1 eq) in POCl3 (8.5 mlmmol/eq) was heated under reflux over night. The excess POCl3 was removed under reduced pressure, then the residue was poured onto ice. The mixture was extracted with EtOAc (30 mlmmol/eq) and NaHCO3 (25 ml*mmol/eq). The organic layer was dried over MgSO4 and concentrated in vacuum. The crude residue was purified by flash column chromatogaphy to give the pure title compounds.

Reference： [1]Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella [European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68]

81
[ 667-27-6 ]
[ 5409-31-4 ]
C₁₄H₁₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; copper(II) acetate monohydrate at 100℃; for 24h; Sealed tube;

Reference： [1]Tao, Na; Wang, Jie; Yuan, Chunchen; Zeng, Runsheng; Zhao, Ying-Sheng [Organic Letters, 2019, vol. 21, # 21, p. 8607 - 8610]

82
[ 461-82-5 ]
[ 5409-31-4 ]
3,4-diethoxy-N-(4-(trifluoromethoxy)phenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With phosphorus trichloride In toluene Reflux;

Reference： [1]Grau, Kathrin; Hagenow, Jens; Hagenow, Stefanie; Hefke, Lena; Khanfar, Mohammad; Proschak, Ewgenij; Stark, Holger [Drug Design, Development and Therapy, 2020, vol. 14, p. 371 - 393]

83
[ 5409-31-4 ]
[ 121-87-9 ]
3,4-diethoxy-N-(2-chloro-4-nitrophenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With phosphorus trichloride In toluene Reflux;

Reference： [1]Grau, Kathrin; Hagenow, Jens; Hagenow, Stefanie; Hefke, Lena; Khanfar, Mohammad; Proschak, Ewgenij; Stark, Holger [Drug Design, Development and Therapy, 2020, vol. 14, p. 371 - 393]

84
[ 5409-31-4 ]
[ 106-40-1 ]
3,4-diethoxy-N-(4-bromophenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With phosphorus trichloride In toluene Reflux;

Reference： [1]Grau, Kathrin; Hagenow, Jens; Hagenow, Stefanie; Hefke, Lena; Khanfar, Mohammad; Proschak, Ewgenij; Stark, Holger [Drug Design, Development and Therapy, 2020, vol. 14, p. 371 - 393]

85
[ 121-01-7 ]
[ 5409-31-4 ]
3,4-diethoxy-N-(4-nitro-2-(trifluoromethyl)phenyl)benzamide [ No CAS ]

Reference： [1],2020,vol. 14,p. 371 - 393

86
[ 121882-74-4 ]
[ 5409-31-4 ]
bis(3,4-diethoxybenzoato)tri(p-tolyl)bismuth(V) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In toluene Inert atmosphere;	The second step involves the preparation of target compounds (1-8) by using stoichiometric amounts of the respective carboxylic acid (1mmol), Ar3BiBr2 (0.5mmol) and triethylamine (1mmol) as base in 20mL toluene. The reaction mixture was refluxed for 3-4h at room temperature under argon gas. The triethylammonium bromide salt, thus formed, was filtered off and the clear filtrate was allowed to evaporate at room temperature for solidification which was subsequently recrystallized in a mixture of chloroform and pet-ether (3:1) to get the pure compound(s) as illustrated in Scheme- 1.

Reference： [1]Abbas, Sumaira; Azam, Syed Sikander; Ihsan-ul-Haq; Imtiaz-ud-Din; Mehmood, Mehwish; Parvaiz, Nousheen; Tahir, Muhammad Nawaz; Tameez Ud Din, Asim [Journal of Organometallic Chemistry, 2020, vol. 921]

87
[ 5409-31-4 ]
[ 7065-17-0 ]
bis(3,4-diethoxybenzoato)triphenylbismuth(V) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine In toluene Inert atmosphere;	The second step involves the preparation of target compounds (1-8) by using stoichiometric amounts of the respective carboxylic acid (1mmol), Ar3BiBr2 (0.5mmol) and triethylamine (1mmol) as base in 20mL toluene. The reaction mixture was refluxed for 3-4h at room temperature under argon gas. The triethylammonium bromide salt, thus formed, was filtered off and the clear filtrate was allowed to evaporate at room temperature for solidification which was subsequently recrystallized in a mixture of chloroform and pet-ether (3:1) to get the pure compound(s) as illustrated in Scheme- 1.

Reference： [1]Abbas, Sumaira; Azam, Syed Sikander; Ihsan-ul-Haq; Imtiaz-ud-Din; Mehmood, Mehwish; Parvaiz, Nousheen; Tahir, Muhammad Nawaz; Tameez Ud Din, Asim [Journal of Organometallic Chemistry, 2020, vol. 921]

88
[ 5409-31-4 ]
[ 122502-94-7 ]
1-[5-(3,4-diethoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}-1H-1,2,3-benzotriazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With trichlorophosphate at 35℃; for 4h; Sonication; Green chemistry;	Method 2. General procedure: An equimolar mixture of compound 3 (10 mmol) and substituted aryl carboxylic acid (10 mmol) in phosphoryl chloride (10 mL) was sonicated at 35 °C, 40 Hz for 4-6 h in ultrasound bath. Then the reaction mixture was cooled, poured into ice-cold water and neutralized with 20% NaHCO3 solution. The formed solid was filtered, washed with water and recrystallized from ethanol to give the target compound.

Reference： [1]Emre Eyupoglu, Ozan; Keskin, Ilknur; Mermer, Arif; Mervenur Kalender, Semiha; Tuzun, Burak; Volkan Bulbul, Muhammet [Journal of Molecular Liquids, 2022, vol. 359]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	5409-31-4	MDL No. :	MFCD00002504
Formula :	C₁₁H₁₄O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VVKCVAPLTRZJHH-UHFFFAOYSA-N
M.W :	210.23	Pubchem ID :	79417
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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P103	Read label before use
Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
P301	IF SWALLOWED:
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P321
P322
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P342	If experiencing respiratory symptoms:
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 5409-31-4 ] {[proInfo.proName]}

Quality Control of [ 5409-31-4 ]

Related Doc. of [ 5409-31-4 ]

Product Details of [ 5409-31-4 ]

Safety of [ 5409-31-4 ]

Application In Synthesis of [ 5409-31-4 ]

[ 5409-31-4 ] Synthesis Path-Upstream 1~1

[ 5409-31-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 5409-31-4 ]

Aryls

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 5409-31-4 ] {[proInfo.proName]}

Quality Control of [ 5409-31-4 ]

Related Doc. of [ 5409-31-4 ]

Product Details of [ 5409-31-4 ]

Safety of [ 5409-31-4 ]

Application In Synthesis of [ 5409-31-4 ]

[ 5409-31-4 ] Synthesis Path-Upstream 1~1

[ 5409-31-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 5409-31-4 ]

Aryls

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5409-31-4 ]