Tag: M.W=100-200

Reference of 1678-68-8, These common heterocyclic compound, 1678-68-8, name is trans-Ethyl 4-aminocyclohexanecarboxylate, 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.

1-(2-Methanesulfonylpyrimidin-4-yl)-1H-indazole (6.4 g) was suspended in THF and the mixture heated to 60 C. until complete dissolution of the solids. trans-4-Amino-cyclohexane-carboxylic acid ethyl ester (7.99 g, 46.6 mmol) was added, followed by TEA (9.7 mL, 69.9 mmol), and the resulting mixture stirred overnight. The reaction mixture was concentrated under reduced pressure until solids started to precipitate, and was then heated to 60 C. for 24 h. THF (4 mL) was added, and the reaction mixture stirred for 64 h at 60 C. The resulting mixture was extracted with EtOAc, the combined organic extracts washed with water, dried over MgSO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM/MeOH, 98:2) and the brown solid obtained was triturated with Et2O to give trans-4-(4-indazol-1-ylpyrimidin-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (2.883 g) as a white solid.

Statistics shows that trans-Ethyl 4-aminocyclohexanecarboxylate is playing an increasingly important role. we look forward to future research findings about 1678-68-8.

Reference:
Patent; Roche Palo Alto LLC; US2008/146565; (2008); A1;,
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Synthetic Route of 369-26-6, 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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 40 mL reaction vessel was charged 8-chloro-N-(2-fluorobenzyl)-N-(2- hydroxyethyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide (I-73) (0.10 mmol) and CH2Cl2 (10 mL) followed by the addition of commercial Dess-Martin Periodinane (Sigma- Aldrich, 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H-one, 0.20 mmol) and buffered with solid sodium bicarbonate (0.20 mmol). The milky white suspension was rapidly stirred for 2 hrs and then the reaction was then directly diluted with ethyl acetate (150 mL) and washed with water (3 x 15 mL). The resulting organic extract was concentrated to a residue (in vacuo) and used directly without delay or further manipulation. The residue was dissolved in 9:1 MeOH/AcOH (5 mL) and treated with methyl-3-amino benzoate (0.40 mmol). The resulting reaction was then stirred at room temperature for 30 mins. and then treated with sodium cyanoborohydride (1.0 mmol, portion-wise over 30 mins.) followed by stirring at room temperature for an additional 1 hr. The resulting reaction was diluted with ethyl acetate (150 mL) and washed with water (3 x 25 mL). The resulting organic extracts were concentrated in vacuo and then directly subjected to reverse phase chromatography using TFA-modified (0.05 percent) water/ACN (35 to 80 percent). All fractions were reduced to dryness under vacuum and subjected to a free base event using polymer immobilized carbonate (SPE-C03H Varian cartridge, 0.90 nominal load with MeOH mobilizer, 10 mL) to give methyl 3-((2-(8-chloro-N-(2- fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)ethyl)amino) benzoate (63-lnt) as a white solid. 1H NMR (400 MHz, d4-MeOH): delta 7.48-7.19 (m, 8H), 7.03- 6.92 (3H), 7.18 (app d, J = 8.0 Hz, 1 H), 6.62 (app dt, J = 12.2, 8.0 Hz, 1 H), 5.30-5.20 (m, 2H), 4.83 (br s, 2H), 4.21 (t, J = 5.0 Hz, 2H), 3.85 (s, 3H), 3.74 (s, 3H), 3.38 (t, J = 5.0 Hz, 2H). Mixture of rotamers. MS (m/z): 549.2/551.2 (M+H)+(chlorine isotope pattern).

The synthetic route of Methyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; CHIANELLI, Donatella; LIU, Xiaodong; MOLTENI, Valentina; NELSON, John; ROLAND, Jason; RUCKER, Paul; TULLY, David; WO2015/69666; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 103-25-3, name is Methyl 3-phenylpropionate, 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 103-25-3, Computed Properties of C10H12O2

In the 10mL single-mouth bottle,Nitrogen protection,82.1 mg (0.50 mmol) of compound 1e is added,2.5mL n-pentane,105.9 mg (2.25 mmol) deuterated ethanol (EtOD),16.0 mg (2.25 mmol) lithium block,Stir for 5 min at 0C.Rise to room temperatureThe reaction was quenched with 3.0 M aqueous hydrochloric acid.Add ether and saturated salt,59.0 mg of target compound 4a was obtained.Yield 85%.

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; China Agricultural University; An Jie; Lei Peng; Han Minhui; Ma Xiaodong; Wu Yufei; A Dila·adijiang; Ding Yuxuan; (15 pag.)CN107445798; (2017); A;,
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These common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, 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. Product Details of 57486-68-7

To a stirred solution of 54 (300 mg, 1.75 mmol) and methyl 2-(2- chlorophenyl)acetate 55 (325 mg, 1.75 mmol) in dry DMA (4 mL), KF/AI2O3 (1800 mg, 40 wt %) was added and the reaction mixture was stirred at room temperature for 2 h. After completion the reaction mixture was filtered through celite and the residual solid was washed with DCM and filtrate was concentrated. The residue was purified by column chromatography using silica gel (20 % EtOAc/Hexane) to give 56 (400 mg, 75%) as white solid. lH NMR (400 MHz, CDCb) delta (ppm) 8.54 (s, 1H), 7.72 (s, 1H), 7.44-7.39 (m, 1H), 7.34-7.26 (m, 4H), 3.65 (s, 3H).

The synthetic route of Methyl 2-chlorophenylacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF HOUSTON SYSTEM; TRUSTEES OF TUFTS COLLEGE; CUNY, Gregory; NIKHAR, Sameer; DEGTEREV, Alexei; (78 pag.)WO2018/213219; (2018); A1;,
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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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H11NO2

A solution of 3 (244 mg, 1 mmol), methyl 4-(aminomethyl)benzoate 8 (198 mg, 1.2 mmol), and N,N-diisopropylethylamine (174 muL, 1 mmol) in n-butanol (10 mL) was refluxed at 130 C for 36 h. Then saturated NaHCO3 (2.5 mL) was added to neutralize the solution. The mixture was extracted with ethyl acetate, the organic layer was combined, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel chromatography to afford 9 (242 mg, 65% yield). 1H NMR (400 MHz, DMSO-d6) delta: 11.90 (s, 1H), 9.62 (s, 1H), 7.92 (d, J = 7.9 Hz, 2H), 7.82 (s, 1H), 7.45 (d, J = 7.7 Hz, 2H), 6.19 (s, 1H), 5.85 (s, 1H), 4.55 (s, 2H), 3.83 (s, 3H), 2.15 (d, 3H); 13C NMR (100 MHz, DMSO-d6) delta: 166.1, 164.4, 161.7, 160.8, 148.1, 146.1, 138.1, 129.2, 129.1, 127.9, 127.2, 126.9, 95.4, 93.2, 51.9, 43.9, 10.6 ppm. HRMS (ESI-TOF): m/z calcd. for C17H18N6O2Cl, [M+H]+: 373.1174; found: 373.1143.

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:
Article; Luo, Yu; Deng, Yan-Qiu; Wang, Jing; Long, Zi-Jie; Tu, Zheng-Chao; Peng, Wei; Zhang, Ji-Quan; Liu, Quentin; Lu, Gui; European Journal of Medicinal Chemistry; vol. 78; (2014); p. 65 – 71;,
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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. 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 15224-11-0

General Procedure 61 Ethyl 2-[(4-bromo-1H-pyrazol-1-yl)methyl]cyclopropanecarboxylate (4-3): To a reaction solution of ethyl 2-(hydroxymethyl)cyclopropanecarboxylate (4-1) (577 mg; 4.0 mmol) with Et3N (1.1 mL; 8.0 mmol) and DMAP (49 mg; 0.4 mmol) in 12 mL of CH2Cl2 at 0 C. was added methanesulfonyl chloride (0.4 mL; 4.8 mmol). The resulting mixture of brown color suspension was stirred at 0 C. to room temperature under N2 for overnight. The reaction mixture was quenched with NaHCO3, then partitioned between CH2Cl2 (200 mL) and saturated NaHCO3 solution (50 mL); brine (50 mL). The organic layer was dried (Na2SO4), then filtered through silica gel pad, eluted with hexane:EtOAc/1:1. The filtrate was concentrated by vacuum to give 880 mg of ethyl 2-{[(methylsulfonyl)oxy]methyl}cyclopropanecarboxylate as a yellow oil (99% yield). 1H NMR (400 MHz, chloroform-D) delta ppm 0.91-1.02 (m, 1H) 1.26 (q, J=6.99 Hz, 3H) 1.29-1.36 (m, 1H) 1.63-1.74 (m, 1H) 1.79-1.92 (m, 1H) 3.02 (s, 3H) 3.99-4.24 (m, 4H).

The synthetic route of 15224-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
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Related Products of 10601-80-6, 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. 10601-80-6 name is Ethyl 3,3-diethoxypropionate, 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.

General procedure: A mixture of montmorillonite K-10 (75 mg), an appropriate aniline 1 (150 mg, 1.2 mmol), ethyl-3,3-diethoxypropionate (3) (579 mg, 3 mmol) and an aldehyde (166 mg, 1.34 mmol) in pure water (7.5 mL) was stirred at 90 C for the time mentioned in Table 2. After completion of the reaction (indicated by TLC), the mixture was cooled to room temperature and filtered. The filtrate was extracted with EtOAc (3 × 5 mL). The organic layers were collected, combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane to give the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3,3-diethoxypropionate, and friends who are interested can also refer to it.

Reference:
Article; Reddy, T. Ram; Reddy, G. Rajeshwar; Reddy, L. Srinivasula; Meda, Chandana Lakshmi T.; Parsa, Kishore V.L.; Kumar, K. Shiva; Lingappa; Pal, Manojit; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 395 – 404;,
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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. 105-53-3, name is Diethyl malonate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H12O4

General procedure: The respective aldehyde (1-8) (5 mmol) and diethyl malonate(9) (5 mmol) were added in the presence of piperidine (4 mmol)under an inert atmosphere and transformed into a viscous solution. It was refluxed for 5-6 h and quenched with 6 N HCl in cold conditions. The product was extracted with ethyl acetate(3 10 mL). The combined organic extracts were dried and evaporatedunder reduced pressure. Compounds (10-17) were recrystallized from 50% aqueous ethanol and carried forward without further purification.

According to the analysis of related databases, 105-53-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shrivastava, Sushant K.; Srivastava, Pavan; Bandresh, Robin; Tripathi, Prabhash Nath; Tripathi, Avanish; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4424 – 4432;,
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Reference of 1128-00-3, 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. 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-Pentynoic acid (15) (1.00 g, 10.19 mmol) in DCM (20 ml) under argon atmosphere at rt was treated with DMF (39 ll,0.51 mmol) and oxalyl chloride (2.22 ml, 25.48 mmol). The mixture was stirred for 40 min and the volatiles were evaporated. The residue was dissolved in DCM (3 ml) and the obtained solution was added to a mixture of ethyl 2-aminocyclohex-1-ene-1-carboxylate(0.10 g, 0.59 mmol) and DIPEA (1.76 ml, 10.2 mmol) in DCM (15 ml) at 5 C to 2 C under argon atmosphere. The mixture was stirred for 1 h at 0 C and warmed to rt. The mixture was diluted with DCM, washed with saturated NH4Cl, brine, and dried over Na2SO4. The solvent was evaporated and the residue was chromatographed on silica gel (EtOAc in petroleum ether, 1:20 to1:10) to afford a white solid. Recrystallization from n-heptane gave the product 18 (1.20 g). The filtrate after crystallization was concentrated and the residue was chromatographed on Biotage (EtOAcin petroleum ether, 2-20%) to give the product (0.25 g); the combined yield was 1.45 g, 57%. 1H NMR (300 MHz, CDCl3) d: 11.66(s, 1H), 4.18 (q, J = 7.1 Hz, 2H), 3.03-2.92 (m, 2H), 2.65-2.49 (m,4H), 2.36-2.25 (m, 2H), 1.97 (t, J = 2.3 Hz, 1H), 1.70-1.54 (m, 4H),1.30 (t, J = 7.1 Hz, 3H). 13C NMR (75 MHz, CDCl3) d: 170.1, 169.6,152.1, 104.9, 82.8, 69.2, 60.4, 37.2, 28.7, 24.3, 22.0, 21.8, 14.6,14.4. LCMS (ESI) m/z 250.18 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-aminocyclohex-1-enecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bobileva, Olga; Ikaunieks, Martins; Duburs, Gunars; Mandrika, Ilona; Petrovska, Ramona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4314 – 4329;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: trans-Ethyl 4-hydroxycyclohexanecarboxylate

4-Toluenesulfonyl chloride (18.29 g, 96 mmol) was added in several portions to a solution of ethyl 4-hydroxycyclohexanecarboxylate (ca. 1:1 mixture of cis and trans ring isomers) (29.5 g, 90 mmol) in pyridine (100 mL) in an ice-water bath, and the mixture stirred, allowing to warm to RT. After the solid had dissolved, the mixture was allowed to stand. After 24 h, the mixture was concentrated and the residue partitioned between water and EtOAc (100 mL each). The organic phase was dried and concentrated to give ethyl 4-(tosyloxy)cyclohexanecarboxylate (ca. 1:1 mixture of cis and trans ring isomers) (crude, 29.5 g) as a colourless oil which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) delta ppm 1.20-1.30 (m, 3H) 1.44-2.08 (m, 8H) 2.21-2.43 (m, 1H) 2.48 (s, 3H) 4.08-4.20 (m, 2H) 4.40-4.50 and 4.70-4.78 (both m, total 1H) 7.28-7.40 (m, 2H) 7.78-7.86 (m, 2H)

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; US2015/57298; (2015); A1;,
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