Month: March 2021

Synthetic Route of 42122-75-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example (Ik-2) 2-Chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoic acid 6.74 g (36.3 mmol) of methyl 5-amino-2-chlorobenzoate, 0.22 g (1.8 mmol) of 4-N,N-dimethylaminopyridine and 9.49 ml (54.4 mmol) of N-ethyldiisopropylamine are dissolved in 50.0 ml of ethyl acetate and cooled to 0 C. A solution of 6.0 g (18.1 mmol) of 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride in 100 ml of ethyl acetate is added over the course of an hour to this reaction mixture. When the addition is complete, the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with 250 ml of ethyl acetate and the organic phase is then washed three times with in each case 100 ml of 1M hydrochloric acid, three times with 1M sodium hydroxide solution and once with saturated sodium chloride solution. This gives 8.0 g of a mixture of methyl 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoate and methyl 5-(bis{[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)-2-chlorobenzoate in the ratio 6:4.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 5-amino-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer CropScience AG; US2011/301181; (2011); A1;,
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Application of 1000342-11-9,Some common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, molecular formula is C9H10BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

01035] Step 4: methyl 3-bromo-5-(cyclopentylamino)benzoate[01036] To a stirred solution of ethyl 3-amino-5-bromobenzoate (2 g, 8.73 mmol) and cyclopentanone (2.2 g, 26.1 mmol) in methanol (20 mL), acetic acid (1.04 g, 17.4 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.37 21.83 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford desired compound ( 1 .6 g, 61 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-5-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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Electric Literature of 18013-97-3, A common heterocyclic compound, 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, molecular formula is C12H12Br2O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

60 g (160 mmol) of diethyl dibromoterephthalate, 43 g (320 mmol) of o-tolylboronic acid, 365 mg (0.32 mmol) of Pd(PPh3)4 and 92 g (660 mmol) of K2CO3 are heated at the boil for 4 h in 300 ml of toluene and 300 ml of water. The mixture is subsequently partitioned between toluene and water, and the organic phase is washed three times with water and dried over Na2SO4. The residue remaining is recrystallised twice from heptane to give colourless crystals. The yield is 51 g (127 mmol, 81%).

The synthetic route of 18013-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; US2011/92701; (2011); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 10602-06-9, name is Methyl 3-ethynylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 3-ethynylbenzoate

General procedure: To a solution of 9 (9.1 mmol) in THF (18 mL) at room temperature were added alkyne S4-6 (2.0 mL, 14 mmol), PdCl2(PPh3)2 (320 mg, 0.46 mmol), CuI (174 mg, 0.92 mmol) and Et3N (2.5 mL, 18 mmol). After being stirred at room temperature for 1 h, the reaction mixture was quenched with saturated aqueous NH4Cl. The mixture was extracted with AcOEt, washed with saturated aqueous NH4Cl, H2O and brine, dried over Na2SO4, and concentrated. The residue was purified with flash column chromatography to give 10. To a solution of 10 (50 mmol) in MeOH/AcOH (9/1, 1.0 mL) was added Pd(OH)2/C (20%, 35 mg). After being stirred under H2 at room temperature for 5 h, the mixture was filtered through a pad of Celite. The residue was washed with MeOH, and the filtrate was concentrated. The resulting solid was dissolved in 10 mM aqueous monoethanolamine, and purified with high performance liquid chromatography (column: Asahi-pak ODP-50 10E 10 x 250 mm; flow rate 2.0 mL/min; 0-20% MeCN/10 mM monoethanolamine-AcOH pH 9 buffer; detection: UV 254 nm) to give 4a, 4v, 4w, 4dd, 5q-s, 5z, 5aa, 5cc or 6a as monoethanolamine salt.

The synthetic route of 10602-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Inaoka, Daniel Ken; Iida, Maiko; Honma, Teruki; Harada, Shigeharu; Nara, Takeshi; Balogun, Emmanuel Oluwadare; Kita, Kiyoshi; Hashimoto, Satoshi; Tanaka, Akiko; Kita, Kiyoshi; Tabuchi, Toshiyuki; Kuranaga, Takefumi; Inoue, Masayuki; Bioorganic and Medicinal Chemistry; vol. 25; 4; (2017); p. 1465 – 1470;,
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Reference of 33689-29-1, These common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred 0 C solution of methyl l -hydroxyeyclopropane-I- carboxylate (1 16 mg, 1.00 mmol, 1.00 equiv) in DMF (4 mL) was added sodium hydride (60 mg, 1.50 mmol, 1.50 equiv, 60% in mineral oil) in several batches. The resulting reaction mixture was stirred for 0.5 h at 0 C, then 2-(bromomethyl)-l,4- dichlorobenzene (238 mg, 0.99 mmol, 0.99 equiv) was added. The resulting reaction mixture was stirred for 1 h at room temperature and quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (3×20 mL) and the combined organic layers washed with, brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide 270 mg (98%) of 85a as a yellow oil.

The synthetic route of 33689-29-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18595-12-5, Safety of Methyl 5-amino-2-methylbenzoate

General procedure: To a solution of compound 11a (154 mg, 1.0 mmol) in anhydrous CH2Cl2 (10 mL) was added 3,5-dichlorobenzoyl chloride (209 mg, 1.0 mmol) and pyridine (241 mL 3.0 mmol) under ice bath. After stirring at room temperature for about 8 h, the solvent was removed in vacuum. The resulting residue was dissolved in NaOH (1 M) water solution (3 mL) and CH3OH (3 mL) and stirred for another 2 h. Then the solvent was removed under vacuum, and the residue was acidied to pH 2 or below with HCl (1 M) water solution. The solution was extracted with ethyl acetate twice and the combined organics were dried over anhydrous sodium sulfate and concentrated in vacuum. The resulting residue was puried by silica gel chromatography to give the desired compound as a white solid (234 mg, yield 85.0%)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Gao, Ding-Ding; Dou, Hui-Xia; Su, Hai-Xia; Zhang, Ming-Ming; Wang, Ting; Liu, Qiu-Feng; Cai, Hai-Yan; Ding, Hai-Peng; Yang, Zhuo; Zhu, Wei-Liang; Xu, Ye-Chun; Wang, He-Yao; Li, Ying-Xia; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 44 – 59;,
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Some common heterocyclic compound, 65868-63-5, name is tert-Butyl 6-bromohexanoate, molecular formula is C10H19BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: tert-Butyl 6-bromohexanoate

To a stirred mixture of alcohol 32 (49.7 mg, 0.10 mmol) and TBAI (3.7 mg,0.01 mmol) in DMF (1 mL) at rt was NaH (4.4 mg, 60% dispersion in mineraloil, 0.11 mmol). After 30 minutes, tert-butyl bromohexanoate (25.1 mg, 0.1mmol) was added and the solution was stirred for a further 16 h at rt. H2O (1mL) was then added, and the mixture was extracted with ether (3 ¡Á 2 mL), driedover MgSO4, filtered and concentrated in vacuo. The resultant crude oil was purified by flashchromatography (EtOAc-hexanes 1:3) giving the product as a pale oil (10 mg, 17%). vmax(neat)/cm-12856, 1727, 1367, 1104, 845; deltaH (400 MHz; CDCl3), 7.41 (d, J = 2.0 Hz), 7.32 (dt, J = 8.3, 1.7, 2H),7.27 (m, 2H), 7.03 (dt, J = 8.5, 2.0, 2H), 3.60 (t, J = 6.8, 2H) 3.47 (q, J = 6.4, 2H), 2.87 (t, J = 4.8, 4H),2.66 (t, J = 7.1, 2H), 2.37 (s, 3H), 2.20 (m, 4H), 1.75 (m, 4H), 1.60 (m, 6H), 1.44 (s, 9H); HRMS (ESI+)[M + H]+ 667.2817 calcd for C36H45Cl2N4O4 667.2812.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65868-63-5, its application will become more common.

Reference:
Article; Grant, Phillip S.; Kahlcke, Nils; Govindpani, Karan; Hunter, Morag; MacDonald, Christa; Brimble, Margaret A.; Glass, Michelle; Furkert, Daniel P.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 21; (2019);,
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Some common heterocyclic compound, 939-18-4, name is 3-Bromo-2H-chromen-2-one, molecular formula is C9H5BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 3-Bromo-2H-chromen-2-one

Step 2: 3-({3-[4-(isoquinolin-1 -yl)piperazin-1 -yl]propyl}amino)-2H-chromen- 2-one hydrochloride (87) A mixture of intermediates 31 b (50 mg, 0.185 mmoles, 1 eq.) and 87a (50 mg, 0.222 mmoles, 1 .2 eq.), Pd(OAc)2 (5 mg, 0.019 mmoles, 0.1 eq.), Xantphos (1 1 mg, 0.019 mmoles, 0.1 eq.) and Cs2C03 (90 mg, 0.28 mmoles, 1 .5 eq.) in 1 ,4-dioxane (2.5 ml_) was heated to 130C in a sealed tube under microwave irradiation for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel (SNAP25) eluting with a gradient of 0-2% mixture A in dichloromethane, where mixture A is MeOH/NH4OH 10:1 . The partially pure product was further purified by preparative LC-MS to give 20 mg of a yellow gum. The product was dissolved in dichloromethane (4 mL) and treated with 1 M HCI solution in diethyl ether (0.16 mL) causing precipitation. The resulting mixture was evaporated under reduced pressure and the residue was triturated with diethyl ether. The solids were dried to give 24 mg of 3-({3-[4-(isoquinolin-1 – yl)piperazin-1 -yl]propyl}amino)-2H-chromen-2-one hydrochloride 87 (Y=27%). LC-MS (M-H+) = 415.3. 1 H NMR (400MHz, DMSO-d6) delta = 1 1 .1 6 (br. s., 1 H), 8.19 (d, J=7.5 Hz, 1 H), 8.08 (d, J=5.8 Hz, 1 H), 8.00 (d, J=7.5 Hz, 1 H), 7.85 (t, J=6.5 Hz, 1 H), 7.70 (t, J=7.3 Hz, 1 H), 7.57 (d, J=5.3 Hz, 1 H), 7.47 (br. s., 1 H), 7.37 – 7.10 (m, 3H), 6.68 (s, 1 H), 6.27 (br. s., 1 H), 4.00 (d, J=12.3 Hz, 2H), 4.37 – 3.81 (m, 1 H), 3.64 (d, J=1 1 .0 Hz, 4H), 3.40 (d, J=9.3 Hz, 2H), 3.28 (d, J=5.8 Hz, 4H), 2.1 1 (br. quin, J=7.0 Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-18-4, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; GAROFALO, Barbara; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; CORSO, Gaia; MAGARO’, Gabriele; FURLOTTI, Guido; IACOANGELI, Tommaso; (108 pag.)WO2016/96631; (2016); A1;,
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Synthetic Route of 25597-16-4, The chemical industry reduces the impact on the environment during synthesis 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, I believe this compound will play a more active role in future production and life.

EXAMPLE 14 STR89 Step A: Preparation of 4,4,4-Trifluorocrotonic acid A solution of ethyl 4,4,4-trifluorocrotonate (9.85g, 65.9 mmole) and 1N NaOH (92.3 mL, 92.3 mmole) in THF (24 mL) was stirred at room temperature for 3 hours. The pH was brought to 1 with conc. HCl and the mixture extracted with Et2 O (3*). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound as an oil. NMR (CDCl3): delta 6.55 (d, 1H); 6.89 (dq, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US6048869; (2000); A;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 69812-51-7, Safety of Methyl 4-chlorosulfonylbenzoate

Under Ar protection,Compound 26b (0.7 g, 2.98 mmol), 100 mL of dichloromethane,Morpholine (0.31mL, 3.58mmol),Et3N (1.24 mL, 8.94 mmol) was placed in a 250 mL round-bottomed flask and reacted overnight at room temperature. The reaction was detected by TLC the next day.The organic phase was sequentially washed with a 1 mol / L hydrochloric acid aqueous solution and a saturated saline solution.Dry over anhydrous Na2SO4. Concentrated under reduced pressure to obtain Intermediate 27b, 0.78 g of a white solid, with a yield of 91.2%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-chlorosulfonylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Huang Haihong; Li Gang; Wang Pengxu; (55 pag.)CN110759889; (2020); A;,
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