Month: March 2021

Synthetic Route of 7686-78-4, The chemical industry reduces the impact on the environment during synthesis 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, I believe this compound will play a more active role in future production and life.

Preparation method: under an argon atmosphere, add 0.2 mmol of N-pyrimidine porphyrin compound, 0.36 mmol of ethylene cyclopropane compound to a 35 mL Shrek tube.0.008 mmol of [Cp*Rh(CH3CN)3](SbF6)2, 0.08 mmol of 1-adamantanic acid, 0.04 mmol of silver hexafluoroantimonate, methanol 0.5 mL, reacted at 90 C for 12 hours; after the reaction, using acetic acid Ethyl ester was rinsed, concentrated under reduced pressure, and then chromatographed on silica gel (200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio: 0/100 to 100/0). The yield was 81% and E/Z > 20:1.

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, Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengzhou University; Zhu Xinju; Wang Qiuling; Zhi Changlei; Li Jing; Liu Shuang; Zhao Xuemei; Hao Xinqi; Song Maoping; (15 pag.)CN109180648; (2019); A;,
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Reference of 1014645-87-4, The chemical industry reduces the impact on the environment during synthesis 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, I believe this compound will play a more active role in future production and life.

A suspension of 2-(3-(3-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenoxy)azetidin-1-yl)-5-chloronicotinic acid (D110) (150 mg, 0.306 mmol), 1-Hydroxybenzotriazole hydrate (47 mg, 0.306 mmol) and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (88 mg, 0.46 mmol) in dimethylformamide (2 ml) was stirred 40 min at room temperature. A solution of methyl 4-(1-aminocyclopropyl)benzoate (D7) (68.9 mg, 0.306 mmol) and triethylamine (0.042 ml, 0.306 mmol) in dimethylformamide (2 ml) was added and the resulting mixture was stirred 40 min at room temperature. Water (2 ml) was added and the resulting precipitate was collected by filtration and purified by Biotage column (10g) eluting with a mixture dichloromethane/ethylacetate from 100/0 to 80/20. Collected fractions, after solvent evaporation, afforded tert-butyl 4-(3-((1-(5-chloro-3-((1-(4-(methoxycarbonyl)phenyl)cyclopropyl)carbamoyl)pyridin-2-yl)azetidin-3-yl)oxy)phenyl)piperazine-1-carboxylate (135 mg)

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-(1-aminocyclopropyl)benzoate hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Borriello, Manuela; Rovati, Lucio; Stasi, Luigi Piero; Buzzi, Benedetta; Colace, Fabrizio; US2013/261100; (2013); A1;,
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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 22223-49-0 as follows. HPLC of Formula: C9H11NO2

The mixture of pyridine-4-carboxylic acid (1.1199g; 9.0967mmol) dissolved in thionyl chloride (15mL; 206.7748mmol) were mixed and refluxed for 1-3h. Then the excess of thionyl chloride was distilled under vacuum and the aromatic amine methyl ester Ea (1.500g; 9.0816mmol) dissolved in CHCl3 (20mL; 249.6231mmol) was added. The mixture was heated and stirred under reflux for 3-6h. The amide (L2: yield ca. 50%; 1.2212g; 3.5627mmol) was precipitated as yellow crystals after washing the dark yellow oil with diethyl ether and recrystallization with the mixture of acetone and methanol (m.p. 180C). Anal. Calc. for (C15H15N2O3)Cl(H2O)2: C, 52.56; H, 5.59; N, 8.17. Found: C, 52.39; H, 6.30; N, 8.16. FT-IR (KBr): 3435cm-1 nu(O-H), 3218cm-1 nu(N-H), 3056, 2924, 2852cm-1 nu(C-H), 1730 and 1640cm-1 nu(C=O), 1603-1441cm-1 nu(ringC=C), 1317-1088cm-1 nu(C-O) and nu(C-N) overlapped, 803/750cm-1 delta(ringC=C)oop. 1H NMR (403MHz, d-DMSO, ppm) delta: 10.71 (s, 1H) – 9, 9.04 (dd, J=4.98, 1.52Hz, 2H) – 2/4, 8.28 (dd, J=4.96, 1.54Hz, 2H) -1/5, 7.71 (m, 1H) – 14, 7.57 (ddd, J=7.64, 1.53, 0.72Hz, 1H) – 12, 7.38 (t, 1H) – 13, 4.41 (s, 12H N+-H protone – fast chemical exchange with water molecules) – 3, 3.72 (s, 3H) – 20, 2.30 (s, 3H) -16. 13C NMR (151MHz, d-DMSO, ppm) delta: 166.32-17, 162.88-7, 146.52-2/4, 145.42-6, 136.54-11, 134.61-10, 134.33-12, 128.25-15, 127.95-14, 126.95-13, 123.44-1/5, 52.10-20, 17.86-16.

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Barczy?ski, Piotr; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1145; (2017); p. 86 – 93;,
Ester – Wikipedia,
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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. 5326-50-1, name is Ethyl 2-(1-hydroxycyclohexyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H18O3

Reference Example 62; [1-(Benzoylamino)cyclohexyl]acetic acid; To a mixture of ethyl (1-hydroxycyclohexyl)acetate (17.1 g, 92.1 mmol) and benzonitrile (9.5 ml, 92.1 mmol) was added conc. sulfuric acid (50 ml) at 0C, and the mixture was stirred at room temperature for 12 hrs. Water (200 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, and then with saturated brine and dried over anhydrous MgS04. After concentration under reduced pressure, ethanol (50 ml) and 50% aqueous potassium hydroxide solution (10 ml) were added to the residue, and the mixture was heated under reflux for 6 hrs. Water (400 ml) was added to the reaction mixture, and the mixture was washed with diethyl ether. The aqueous layer was acidified (pH 2) with 5N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The obtained solid was recrystallized from ethanol-toluene to give the title compound (18.1 g, 75%) as colorless crystals. ?H-NMR (CDCl3) No.:1.14-1.62 (8H, m) , 2.25-2.43 (2H, m) , 2.74 (2H, s), 3.32 (lH, s), 7.36-7.57 (3H, m), 7.73-7.80 (2H, m), 11.93 (lH, s). LC/MS (ESI) m/z: 262 (MH(at)).

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 5326-50-1.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/105802; (2005); A1;,
Ester – Wikipedia,
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Related Products of 18595-12-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 18595-12-5 name is Methyl 5-amino-2-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of THF (5 mL) containing compound 3 (350 mg, 1.03 mmol) were added sequentially, HOBT (224 mg,1.6 mmol), EDC.HCl (306 mg, 1.6 mmol), TEA (0.28 mL, 2.0 mmol) and methyl 5-amino-2-methylbenzoate (3a) (198 mg, 1.2 mmol). The resulting mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with dichloromethane (10 mL) followed by water (15 mL), the organic layer was separated, washed with water (2 ¡Á 15 mL) followed by brine solution to obtain the crude compound 4. The crude compound was purified by column chromatography using 60-120 silica gel and eluted with 30 % EtOAc/hexane to afford compound 4. Pale white solid; Yield: 280 mg, 66 %; m.p.: 160-162 C; IR (neat, numax): 3431, 2925, 2858, 1620,1442, 1255, 1219, 1170, 1079, 954; 1H NMR: (CDCl3, 400 MHz): delta 7.96 (br.s, 1H-NH), 7.66 (d, J = 6.4 Hz, 1H), 7.46 (t, J = 7.2 Hz, 1H), 7.34 (d, J = 7.6Hz, 1H), 7.22 – 7.33 (d, 4 H),4.68 (br.p, 1H), 3.90 (s, 3H), 3.8(t,1H),3.06 (br.t, 2H) 2.55 (s,3 H)2.47(q, 1H) 1.87-2.03 (m, 4 H). ESI MS: m/z (rel. abund.%): 465.37 (M+,100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Reddy; Prasad; Venkataramana; Asian Journal of Chemistry; vol. 28; 1; (2016); p. 138 – 142;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 18583-89-6, A common heterocyclic compound, 18583-89-6, name is Methyl 3-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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.

When the same reaction as in Referential Example 18 is carried out using methyl 3-amino-2-methylbenzoate instead of the starting methyl 3-amino-6-methylbenzoate, 2-methyl-3-(1-pyrrolyl)benzyl alcohol is obtained.

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; Banyu Pharmaceutical Co., Ltd.; US5234946; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate, molecular formula is C9H9BrO3, 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. Application In Synthesis of Methyl 4-bromo-2-methoxybenzoate

Step 1: Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoateTo a 100 mL round-bottomed flask equipped with a stir bar was added methyl 4- bromo-2-methoxybenzoate (1.79 g, 7.30 mmol), 4,4,4?,4?,5 ,5 ,5?,5?-octamethyl-2,2?- bi(1,3,2-dioxaborolane) (2.78 g, 10.9 mmol), PdCl2(dppf) (0.267 g, 0.365 mmol), and potassium acetate (2.15 g, 21.9 mmol) at ambient temperature. The flask was sealed witha septum, dioxane (36.5 ml) was added, and the atmosphere was purged with N2 (g). The reaction was then heated to 90 C with stirring for 3 h and cooled to room temperature. The reaction was concentrated, the residue was dissolved in EtOAc and washed with 1 M aq. HC1 and sat. aq. NaC1. The organics were dried (Na2504), filtered, and concentrated. The residue was purified by silica gel column chromatography (Teledyne ISCOCombiFlash Rf, gradient of 0% to 100% using solvent A/B=CH2C12/EtOAc over 15 column volumes, RediSep 5i02 80 g, loaded as DCM solution) to afford (methyl 2- methoxy-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzoate (1 .87 g, 88 %) as a tan solid: ?H NMR (400 MHz, CDC13) oe 7.76 (d, J=7.7 Hz, 1 H), 7.42 (dd, J=7.7, 0.9 Hz, 1 H), 7.39 (s, 1 H), 3.96 (s, 3 H), 3.90 (s, 3 H), 1.36 (s, 12 H); HPLC: RT=1.284 mm(Waters Acquity BEH C,8 1.7 urn 2.0 x 50 mm, CH3CN/H20/0. 1% TFA, 1.5 mill gradient, wavelength=254 nm); MS (ES): mlz= 293 [M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 139102-34-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 623-53-0, name is Ethyl methyl carbonate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl methyl carbonate

47 mmol of the above intermediate I, 3-trifluoromethyl-4-chloroaniline 47 mmol and 0.4 mmol of benzyltrimethylammonium hydroxide weredissolved in 100 mL of N-methylpyrrolidone, and ethyl methyl carbonate 50 mmol was added dropwise in portions. The temperature was raised to 50 C for 80 min, cooled to room temperature, and the reaction solution was added to a mixed solvent of 60 mL of water and 40 mL of ethyl acetate, stirred, layered, and the aqueous phase was extracted with ethyl acetate. The sodium chloride was washed, dried, and dried under vacuum at 40 C to obtain 20.99 g of crude sorafenib in a yield of 96.1%.

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; Shandong Luoxin Pharmaceutical Group Hengxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Hou Junkai; Liu Qingli; Tian Song; (13 pag.)CN108276327; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: Methyl 4-chlorosulfonylbenzoate

Step J1 -2: methyl 6-(benzyloxy)-N-{ [4-(methoxycarbonyl)phenyl]sulfonyl}-L-norleucinate. To a solution of methyl 6-(ben2yloxy)-L-norleucinate hydrochloride (15 g, 52.1 mmol) in DCM (261 mL) was added triethylamine (15.98 mL, 115 mmol) followed by 4- carbomethoxy-phenylsulfonyl chloride (12.48 g, 53.2 mmol) by portions. After 15 minutes of stirring at room temperature, the reaction mixture was concentrated in vacuo to 1/3 volume, diluted with EtOAc, washed with 10% KHSO4, saturated aqueous NaHCtheta3, and then brine, and then dried over sodium sulfate and concentrated in vacuo to give the desired product as a crude solid. MS M+l = 450.

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/42093; (2009); A1;,
Ester – Wikipedia,
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Application of 7459-46-3,Some common heterocyclic compound, 7459-46-3, name is Triethyl ethane-1,1,2-tricarboxylate, molecular formula is C11H18O6, 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 reflux solution of triethyl 1,1,2-ethane tricarboxylate (32) (5.0 g, 20.3 mmol) and sodium borohydride (2.3 g, 60.9 mmol) in tert-butyl alcohol (40 mL), methanol (2.5 mL) was added in the reaction mixture in three aliquots over 0.5 h. The resulting solution was heated under reflux condition for additional 0.5 h and allowed to cool down to room temperature. 1 N HCl was added with care until the solution was neutral. The solution was filtered and filtrate was extracted with ethanol. The residue was purified by silica gel column chromatography (chloroform:methanol = 7:1) to give 33 (2.1 g). Yield: 88percent; 1H NMR (300 MHz, CDCl3) delta (ppm) 3.80 (m, 6H), 1.93 (q, J = 5.4 Hz, 1H), 1.71 (m, 2H); ESI [M + H] = 121.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Triethyl ethane-1,1,2-tricarboxylate, its application will become more common.

Reference:
Article; You, Hyun; Youn, Hyung-Seop; Im, Isak; Bae, Man-Ho; Lee, Sang-Kook; Ko, Hyojin; Eom, Soo Hyun; Kim, Yong-Chul; European Journal of Medicinal Chemistry; vol. 46; 4; (2011); p. 1153 – 1164;,
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