Tag: M.W=100-200

Synthetic Route of 294190-18-4,Some common heterocyclic compound, 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, molecular formula is C9H10ClNO2, 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.

[01289] Step 1 : Synthesis of methyl 3-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-5-chloro- 2-methylbenzoate[01290] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1 g, 4.6 mmol) and tert-butyl (2-oxoethyl)carbamate ( 1 .4 g, 8.8 mmol) in methanol ( 10 mL), acetic acid (0.027 g, 4.6 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.352 g, 4.68 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 the desired product (0.62 g, 38 %).

The synthetic route of 294190-18-4 has been constantly updated, and we look forward to future research findings.

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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Reference of 2216-92-4, The chemical industry reduces the impact on the environment during synthesis 2216-92-4, name is N-Phenylglycine Ethyl Ester, I believe this compound will play a more active role in future production and life.

Example 35 1, 1-Dioxo-5-phenyl-1, 2, 5-thiadiazolidin-3-one sodium salt A. N-sulfamoylated-N-phenylglycine ethyl ester; A solution N-phenylglycine ethyl ester (1.0 g, 5.58 mmol) and TEA (1.69 g, 16. 7 mmol) in MeCN, 3mL is added dropwise to a freshly prepared solution of sulfamoyl chloride (5.58 mmol) in MeCN (5mL) over 20 min. The mixture is stirred at room temperature (RT) for 16 h. The solvent is evaporated and the residue is partitioned between EtOAc and water. The organic layer is dried over anhydrous sodium sulfate (Na2SO4) and evaporated. The residue is flash chromatographed on silica gel using 30% No. 50% EtOAc in hexanes as eluent to afford the N-sulfamoylated-N-phenylglycine ethyl ester as a yellow solid : [M+1] + = 259.

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, N-Phenylglycine Ethyl Ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2003/82841; (2003); A1;,
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Reference of 431-47-0,Some common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, molecular formula is C3H3F3O2, 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.

Propargyl amine (4.00 g, 72.62 mmol, 1.00 equiv.) was added dropwise to methyl trifluoroacetate (11.16 g, 87.15 mmol, 1.20 equiv.) at 0C. The reaction mixture was stirred at 0C for 2 h and then concentrated under reduced pressure to remove methanol. The product was purified by vacuum distillation yielding propargyltrifluoroacetamide as a colorless liquid (9.59 g, 87 %). The structure was confirmed by 1H- and 19F-NMR.

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

Reference:
Patent; Pierce Biotechnology, Inc.; Etienne, Christopher; Opperman, Kay; Kaboord, Barbara; Meier, Scott; Schultz, Jean-Samuel; EP2669291; (2013); A1;,
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Application of 87661-20-9,Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.

Example 193A(+/-)-tert-Butyl 1-[(3-bromo-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate; 42.2 ml (105.5 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to from -20 C. to -30 C., of 14.8 ml (105.5 mmol) of diisopropylamine in 60 ml of abs. THF. After the addition had ended, the mixture was stirred at from -20 C. to -30 C. for another 30 min. The mixture was then cooled to -78 C., and a solution of 12.0 g (84.4 mmol) of tert-butyl cyclopropanecarboxylate in 60 ml of abs. THF was added dropwise at this temperature. After 4 h at -78 C., a solution of 15.4 g (70.3 mmol) of 3-bromo-4-chlorobenzaldehyde in 60 ml of abs. THF was added. The reaction mixture was slowly warmed to RT overnight, saturated aqueous ammonium chloride solution was then added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1?10:1). This gave 16.2 g of the target compound (52.5% of theory).LC-MS (Method 4): Rt=1.47 min; m/z=286/288.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.84-0.99 (m, 2H), 1.02-1.17 (m, 2H), 1.24 (s, 9H), 4.88 (d, 1H), 5.55 (d, 1H), 7.39 (dd, 1H), 7.57 (d, 1H), 7.71 (d, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
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Synthetic Route of 3697-68-5, The chemical industry reduces the impact on the environment during synthesis 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, I believe this compound will play a more active role in future production and life.

To a solution of ethyl l-(hydroxymethyl)cyclopropane-l-carboxylate (3.0 g, 21 mmol) in DCM (50 mL) at -10 C was added DAST (6.0 g, 40 mmol) under Ar. The reaction mixture was stirred as it warmed to ambient temperature over 1 h and continued to stir at that temperature for 23 h. An aqueous solution of HC1 (10%, 5 drops) and H20 (50 mL) were added, and the layers were separated. The aqueous layer was extracted with DCM (50 mL) and the combined organic phases were washed sequentially with H20 (50 mL) and brine (50 mL), dried (MgS04), and filtered. The filtrate was concentrated in vacuo to give ethyl l-(fluoromethyl)cyclopropane-l- carboxylate (3.0 g, yield:99%), which was carried forward without further purification.

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 1-(hydroxymethyl)cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; SCHULZ, Juergen; NEVALAINEN, Marta; DECHANTSREITER, Michael; (273 pag.)WO2019/222101; (2019); A1;,
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These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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. Recommanded Product: trans-Ethyl 4-hydroxycyclohexanecarboxylate

VII) Synthesis of CP30450-3; Ethyl 4-[(/erf-butyldimethylsilyl)oxy]cyclohexanecarboxylate (55); Following protocols reported by Wild,10 a solution of Ethyl 4- hydroxycylohexanecarboxylate (54) (1.0 mL, 6.20 mmol) in DMF (3.0 mL) was treated with imidazole (929 mg, 13.6 mmol) and tert-butyldimethylsilyl chloride (1.22 g, 8.09 mmol) and the resulting mixture stirred magnetically at 18 °C under a nitrogen atmosphere for 20 h. The reaction mixture was then treated with Et2O (50 mL), washed with HCl (1 x 5 mL of a 1 M aqueous solution), then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing residue was subjected to flash chromatography (hexane- 1:49 v/v ethyl acetate/hexane gradient elution) to afford a ca. 1:1 mixture of the cis- and troens-isomeric forms of the title compound 55 (1.78 g, quant.) as a colourless oil, Rf 0.7 in 3:7 v/v ethyl acetate/hexane.1H NMR (300 MHz) delta 4.12 and 4.11 (2 x q, J 7.1 and 7.1 Hz, 2 x 2H), 3.89 and 3.56 (2 x m, 2 x IH), 2.33-2.16 (complex m, 2 x IH), 1.98-1.87 (complex m, 2 x 2H), 1.68-1.22 (complex m, 2 x 6H), 1.25 and 1.24 (2 x t, J 7.1 and 7.1 Hz, 2 x 3H), 0.88 and 0.87(8) (2 x s, 2 x 9H), 0.05 and 0.03 (2 x s, 2 x 6H).13C NMR (75 MHz) delta 175.8 and 175.7 (2 x C), 70.5 and 66.6 (2 x CH), 60.1 and 60.0 (2 x CH2), 42.2 and 42.0 (2 x CH), 34.8 and 32.8 (4 x CH2), 27.2 and 23.4 (4 x CH2), 25.8 and 25.7(7) (6 x CH3), 18.2 and 18.1 (2 x C), 14.2 (2 x CH3), -4.7 and -4.9 (4 x CH3). IR vmax/cm”1 2934, 2858, 1734, 1463, 1252, 1096, 1049, 835, 774.Mass Spectrum (EI) m/z 229 [(M-C4Hg)+’, 92], 57 (100).HRMS found: (M-C4H9)+\ 229.1256. C15H30O3Si requires (M-C4Hg)+’, 229.1260.

The synthetic route of trans-Ethyl 4-hydroxycyclohexanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRYPTOPHARMA PTY LTD; WO2008/124878; (2008); A1;,
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Electric Literature of 1117-71-1, A common heterocyclic compound, 1117-71-1, name is Methyl 4-bromobut-2-enoate, molecular formula is C5H7BrO2, 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 homogeneous solution of (E)-methyl 4-bromobut-2-enoate (53.7 g, 300 mmol) in THF (100 mL) at 0 C (bath temperature) under a nitrogen atmosphere, was added a solution of lithium hydroxide monohydrate (16.4 g, 390 mmol) in water (80 mL) dropwise (over 35 min). After addition the mixture was stirred at 0 “C for 3 h. Cold water (300 mL) and petroleum ether (400 mL) were added and the mixture was stirred at 0 C for 10 min. The organic layer was separated and discarded. Ethyl acetate/petroleum ether (1:10, 300 mL) was then added and-the mixture was again stirred at 0 C for 10 min before the organic layer was separated and discarded. The aqueous solution was acidified with cone, sulfuric acid at 0 C to pH <; 1. The product was extracted into dichloromediane (400 mL; 200 mL) and the combined organic extracts were dried (MgSO4) and evaporated under reduced pressure at 35 C (bath temperature) to give a yellow oil. The oil was stirred with petroleum ether (2x500 mL) at 50 C (bath temperature). The combined petroleum ether extracts were concentrated under reduced pressure at 20-25 C (bath) to induce precipitation of the product The suspension was then stood at 5 UC overnight before the solid was collected by filtration, washed with cold petroleum ether and dried to give (E)-4-bromobut-2-enoic acid (9) (19.9g, 40%). The synthetic route of 1117-71-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AUCKLAND UNISERVICES LIMITED; SMAILL, Jeffrey, Bruce; PATTERSON, Adam Vorn; DENNY, William, Alexander; WILSON, William Robert; LU, Guo-Liang; ANDERSON, Robert, Forbes; LEE, Ho Huat; ASHOORZADEN, Amir; WO2010/104406; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 16017-69-9, name is Ethyl 4-amino-2-chlorobenzoate, 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 16017-69-9, name: Ethyl 4-amino-2-chlorobenzoate

The indicated chloro-aniline (1.02 g, 5.125 mmol) in methanol (13.0 mL) was treated with iodine monochloride (1.0 M in dichloromethane, 5.125 ml, 5.125 mmol) and the solution stirred for 1 hour at room temperature. The reaction mixture was poured into water, followed by aqueous/ethyl acetate work- up, and silica gel chromatography (ethyl acetate : hexanes (2:8) 3.0 % TEA) to give the titled compound.

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; MERCK & CO., INC.; WO2007/81335; (2007); A1;,
Ester – Wikipedia,
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Related Products of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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.

2.1) Diphenyl ether (500 mL, 3.15 mol) was added to a 1 L three-necked flask.After preheating the diphenyl ether in the three-neck flask to 220°C, add step 1.4).Compound II (45.25 g, 0.25 mol) and ethoxylated methyl malonate IIEthyl ester (58.32g, 0.27mol), reaction 1h, to obtain a mixture D;2.2) stirring the mixture D obtained in step 2.1) until it is cooled to 50 ° C to obtain a mixture E;2.3) The mixture E obtained in step 2.2) is filtered, the solid obtained after filtration is washed with methyl tert-butyl ether and dried to obtain compound III (yield 94.59percent)

Statistics shows that Methyl 4-amino-2-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 27492-84-8.

Reference:
Patent; Chongqing University; Dong Lichun; Hu Geng; Li Qi; Liu Dianqing; Wang Haoyuan; (19 pag.)CN107629001; (2018); A;,
Ester – Wikipedia,
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34846-90-7, name is Methyl 3-methoxyacrylate, 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. HPLC of Formula: C5H8O3

To a solution of 1,1,2,2-tetrafluoroethyldimethylamine (96percent, 46 g, 305 mmol) in acetonitrile (100 ml) was added dropwise, at 25° C. under Argon, BF3-etherate (38.9 g, 274 mmol). Subsequently, under reflux conditions (approx. 70° C.), a solution of methyl 3-methoxyacrylate (95percent, 33.5 g, 274 mmol) in acetonitrile (75 ml) was added dropwise to the reaction mixture within 1 h. After stirring under reflux conditions for 21 h, the reaction mixture was cooled to 25° C. The resulting reaction mixture was added dropwise to a solution of methylhydrazine (21 g, 457 mmol) in acetonitrile (48 ml) at 0 to 15° C. within 1.5 h. After stirring at 25° C. for 0.5 h, water (100 ml) was added. The reaction mixture was extracted once with 150 ml and once with 90 ml of methylene chloride. The combined organic phases were washed with water (1.x.200 ml). The resulting organic phase (530 g) contained, according to GC area percent analysis, methyl 3-difluoromethyl-1-methylpyrazole-4-carboxylate and methyl 5-difluoromethyl-1-methylpyrazole-4-carboxylate in a ratio of 6.8:1. According to quantitative HPLC analysis, the organic phase comprised 6.7percent by weight of methyl 3-difluoromethyl-1-methylpyrazole-4-carboxylate. This corresponds to a yield of 68percent (based on methyl 3-methoxyacrylate).

The synthetic route of 34846-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2010/184994; (2010); A1;,
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