Tag: M.W=200-300

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 126541-82-0, name is Methyl 3-amino-4-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-4-(trifluoromethyl)benzoate

Step C: Methyl 3-cyano-4-(trifluoromethyl)benzoateTo a mixture of methyl 3-amino-4-(trifluoromethyl)benzoate (3.2 g, 15 mmol) and aqueous HC1 solution (12 M, 3.5 mL) in water (20 mL) was added dropwise a solution of NaN02 (1.2 g, 17 mmol) in water (7.0 mL) at 5 C. The resulting mixture was stirred for 30 min at 5 C and then added dropwise to a slurry of CuCN (1.3 g, 15 mmol) and KCN (1.6 g, 25 mmol) in water (4 mL), while maintaining the internal temperature between 5-10 C. The mixture was stirred at 10 C for 30 min and then heated at 80 C for 1 h. After cooling, the mixture was extracted with DCM (30 mL x 3). The combined organic layers were washed with brine, dried over Na2S04 and concentrated to afford the title compound. MS: m/z = 230 (M +1). 1H MR (400 MHz, CDC13) delta 8.45-8.53 (m, 1H), 8.33-8.40 (m, 1H), 7.91 (d, 1H, = 8.5 Hz), 4.01 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MITCHELL, Helen; FRALEY, Mark E.; COOKE, Andrew J.; STUMP, Craig A.; BESHORE, Douglas C.; MCCOMAS, Casey C.; SCHIRRIPA, Kathy; ZHANG, Xu-Fang; MCWHERTER, Melody; MERCER, Swati P.; MOORE, Keith; LIU, Chungsing; MAO, Qinghau; (79 pag.)WO2015/143652; (2015); A1;,
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Reference of 1245643-11-1, A common heterocyclic compound, 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, molecular formula is C8H9BrN2O2, 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.

TsOH?H20 (0.388 g, 2.04 mmol) was added to a mixture of triethylorthoformate (6.8 mL, 40.8 mmol) and methyl 3,4-diamino-5-bromobenzoate (5.0 g, 20.4 mmol) in THF (150 mL). The mixture was stirred at 20C for 5 hours. After cooling to room temperature, the mixturewas concentrated under reduced pressure. EtOAc (20 mL) was added to the crude residue and the mixture was filtered. The filter cake was collected to give methyl 7-bromo- 1H- benzo[d]imidazole-5-carboxylate (4.0 g, 77% Yield) as a pink solid. ?H NMR (400 MHz, DMSO) (5 13.10 (br s, 1H), 8.51 (s, 1H), 8.17 (s, 1H), 7.96 (s, 1H), 3.87 (s, 2H).

The synthetic route of 1245643-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; STIVALA, Craig; HEFFRON, Timothy; (243 pag.)WO2019/57946; (2019); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 126430-46-4, name is Benzyl 4-bromobutanoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Benzyl 4-bromobutanoate

Compound 11 was synthesized in accordance with the following scheme. Synthesis of compound 10 is disclosed in J. Le Notre et al.. Adv. Synth. Catal. 349, 432 (2007), and synthesis was carried out on the basis thereof. Compound 9 (102.8 mg, 0.347 mmol, 1 eq.) and compound 10 (756.9 mg, 2.94 mmol, 8.5 eq.) were dissolved in acetonitrile (4 mE), N,N-diisopropylethylamine (512 pL, 2.94 mmol, 8.5 eq.) and a small amount of potassium iodide were added, and the mixture was heated and refluxed for 5.5 hours at 80 C. Water was added and then extracted using dichloromethane, the organic phase was washed using water and a saturated sodium chloride solution and dried using anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by medium-pressure silica gel chromatography (eluent:n-hexane/ethyl acetate=86/14 to 65/35) to obtain the objective compound 11(91.7 mg, 56%). 1H NMR (400 MHz, CDCl3): delta 0.45 (s, 6H), 1.93(quin, 2H, J=7.2 Hz), 2.41 (t, 2H, J=7.2 Hz), 2.90 (s, 3H),2.94 (s, 6H), 3.34 (t, 2H, J=7.2 Hz), 3.95 (s, 2H), 5.10 (s,2H), 6.68 (dd, 1H, J=8.4, 2.8 Hz), 6.74 (dd, 1H, J=8.4, 2.8Hz), 6.95 (d, 1H, J=2.8 Hz), 6.99 (d, 1H, J=2.8 Hz), 7.15 (d,1H, J=8.4 Hz), 7.18 (d, 1H, J=8.4 Hz), 7.31-7.36 (m, 5H); 13C NMR (100 MHz, CDCl3): delta-2.7, 22.4, 31.8, 38.6, 39.2,41.2, 52.4, 66.4, 113.8, 114.2, 117.2, 117.3, 117.7, 128.3,128.4, 128.5, 128.65, 128.67, 134.8, 136.0, 136.1, 136.2,147.3, 148.8, 173.2; HRMS (ESI+): Calcd for [M+H]+,473.26188, Found, 473.26185 (-0.0 mmu).

According to the analysis of related databases, 126430-46-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The University of Tokyo; URANO, Yasuteru; KAMIYA, Mako; MOROZUMI, Akihiko; UNO, Shinnosuke; UMEZAWA, Keitaro; (37 pag.)US2018/52109; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, 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 135484-83-2, Recommanded Product: Methyl 2-amino-4-bromobenzoate

Step 3. Preparation of Methyl 4-bromo-2-isopropoxycarbonylaminobenzoate Add isopropyl chloroformate (104 mL, 104 mmol, 1.0 M in toluene) dropwise to a solution of methyl 2-amino-4-bromobenzoate (14.5 g, 63.0 mmol) and pyridine (10.3 mL, 126.0 mmol) in dichloromethane (210 mL) at room temperature under nitrogen and stir for 5.5 h. Pour the reaction into water (500 mL) and separate the layers. Extract the aqueous layer with dichloromethane (2 x 100 mL) and combine the organic extracts and wash with 2 N HCI, saturated sodium bicarbonate and brine (100 mL each), then dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as a pale orange solid (19.2 g, 96%)

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 2-amino-4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37796; (2005); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 98545-64-3, name is Methyl 4-amino-2-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8BrNO2

To a solution of compound 21 (3g, 13.0mmol) in AcOH (50mL) was added 2,5-dimethoxytetrahydrofuran (2.15g, 16.3mmol). The mixture was heated to reflux and stirred for 4h. After evaporation, the mixture was dissolved in EtOAc, washed with saturated NaHCO3, and dried over anhydrous Na2SO4. The residue after rotary evaporation was purified by column chromatography over silica gel to give compound 22 as a solid (3.06g, 84.3% yield).1H NMR (400MHz, CDCl3): delta 7.92 (d, J=8.5Hz, 1H), 7.70 (d, J=2.3Hz, 1H), 7.35 (dd, J=8.5, 2.3Hz, 1H), 7.10 (t, J=2.2Hz, 2H), 6.38 (t, J=2.2Hz, 2H) and 3.93 (s, 3H) ppm; mp: 50-53C.

According to the analysis of related databases, 98545-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Puhua; Zhang, Jiong; Meng, Qingqing; Nare, Bakela; Jacobs, Robert T.; Zhou, Huchen; European Journal of Medicinal Chemistry; vol. 81; (2014); p. 59 – 75;,
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Adding a certain compound to certain chemical reactions, such as: 7149-03-3, name is Ethyl 4-amino-3-bromobenzoate, 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 7149-03-3, Recommanded Product: 7149-03-3

(3-(Trifluoromethyl)benzyl)zinc pivalate (In) reacts smoothly with 3-bromo-l- (phenylsulfonyl)-lH-indole (5o) and the benzocain derivative 5j, bearing a unprotected amine function, in good yields (66-86 %; entries 22-23).

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:
Patent; LUDWIG-MAXIMILIANS-UNIVERSITAeT MUeNCHEN; KNOCHEL, Paul; BERNHARDT, Sebastian; MANOLIKAKES, Georg; WO2012/85168; (2012); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 680217-71-4, name is Ethyl 2-(2,6-difluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 2-(2,6-difluorophenyl)acetate

General procedure: To a stirred solution of phenyl acetic acid ethyl ester 1a (1 g, 6.09 mmol) in THF (10 mL) was added LiHMDS (9.1 ml, 1 M sol. in THF, 7.31 mmol) at -78 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (1.2 g, 9.146 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at -78 C and stirred at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 4% ethyl acetate/pet ether gave the pure compound 3a (1.1 g, 81% yield) as a colorless liquid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 680217-71-4.

Reference:
Article; Behera, Manoranjan; Venkat Ragavan; Sambaiah; Erugu, Balaiah; Rama Krishna Reddy; Mukkanti; Yennam, Satyanarayana; Tetrahedron Letters; vol. 53; 9; (2012); p. 1060 – 1062;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 15448-76-7, name is Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 15448-76-7

A mixture of dimethyl bicyclo[2.2.1]heptane-l ,4-dicarboxylate (1.0 g, 4.71 mmol) and lithium hydroxide monohydrate (0.593 g, 14.13 mmol) in methanol (20 mL) and water (40 mL) was stirred at ambient temperature for 3 days. Volatiles were removed under vacuum, and the residue was acidified with 1 N HC1 solution. The white suspension was then extracted with ethyl acetate (100 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to give 0.85 g of the title compound as a white solid that was used without further purification.JH NMR (400 MHz, DMSO-

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
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Electric Literature of 541-16-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 541-16-2 as follows.

To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NAOH solution (92.4 g in 185 mL H20) was added 1,2- dibromobutane (30.0 g, 138.9 mmol) and DI-TERT-BUTYLMALONATE (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred 18 h at rt, a mixture of ice and water was then added. The crude product was extracted with CH2CI2 (3x) and sequentially washed with water (3x), brine and the organic extracts combined. The organic layer was dried (MgS04), filtered and concentrated in vacuo. The resulting residue was flash chromatographed (100 G SI02, 3% ET20 in hexane) to afford the titled product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99316; (2003); A1;,
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Reference of 1150566-27-0,Some common heterocyclic compound, 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, molecular formula is C9H8ClN3O2, 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.

[0418] Step 1. 6- [(5-Fluoro-2-hydroxy-benzyl)-methyl-amino] -imidazo [1 ,2-b]pyridazine-3- carboxylic acid ethyl ester (42B). To a mixture of 4-fluoro-2-methylaminomethyl-phenol (20L, 305.2 mg, 1.97 mmol) and 6-chloro-imidazo [1 ,2-b]pyridazine-3-carboxylic acid ethyl ester (42A, 230 mg, 1.02 mmol) in DMSO (5 mL) was added KF (180 mg, 3.01 mmol). The reaction mixture was stirred at 120 C for 18 hours under nitrogen. The solution was then cooled to ambient temperature, diluted with water (20 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were further washed with water (3 x 50 mL) and brine (50 mL), dried over Na2504 and concentrated. The residue was then purified by a silica gel column eluting with EtOAc/hexane (0-50%, 10 CV) to afford the desired product as a white solid (240 mg, 69%). LC-MS (ESI) m/z 345.2 (M+H) ?H NMR (500 MHz, chloroform-d) oe 8.61 (s, 1H),8.17 (s, 1H), 7.91 (d, J= 10.0 Hz, 1H), 7.00-6.86 (m, 4H), 4.78 (s, 2H), 4.47 (qd, J= 7.2, 0.5 Hz, 2H), 3.17 (s, 3H), 1.41 (td, J= 7.1, 0.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, its application will become more common.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; WO2015/112806; (2015); A3;,
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