Month: January 2021

Some common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C8H10O5, 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: 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

4-Chloro-l,7-naphthyridine was prepared as follows (the compound may also be prepared according to the procedure on page 962 in Science of Synthesis, 2005, ,15., 947-985):; – Diisopropylethylamine (58.2 ml) was added to a stirred suspension of 3-aminopyridine- iV-oxide hydrochloride salt (49 g) and 5-(methoxymethylidene)-2,2-dimethyl-l,3-dioxane- 4,6-dione (62.2 g) in isopropanol (150 ml) and the resultant mixture was heated to 9O0C for 20 minutes. The mixture was cooled in an ice bath and the precipitate was isolated and washed in turn with cool isopropanol and diethyl ether and dried under vacuum at 50C. There was thus obtained 2,2-dimethyl-5-[(l -oxidopyridin-3-ylamino)methylidene]-l ,3-dioxane-4,6-dione (81.9 g; 1H NMR Spectrum: (DMSOd6) 1.68 (s, 6H)5 7.44 (m, IH), 7.61 (d, IH), 8.1 (d, IH), 8.52 (2s, IH), 8.66 (s, IH), 11.15 (br s, IH); Mass Spectrum: M-H” 263.; The 4-chloro-l,5-naphthyridine was prepared as follows :; -Diisopropylethylamine (58.2 ml) was added to a stirred suspension of 3-aminopyridine- iV-oxide hydrochloride salt (49 g) and 5-(methoxymethylidene)-2,2-dimethyl-l,3-dioxane- 4,6-dione (62.2 g) in isopropanol (150 ml) and the resultant mixture was heated to 9O0C for 20 minutes. The mixture was cooled in an ice bath and the precipitate was isolated and washed in turn with cool isopropanol and diethyl ether and dried under vacuum at 500C. There was thus obtained 2,2-dimethyl-5-[(l-oxidopyridin-3-ylamino)methylidene]-l,3-dioxane-4,6-dione (81.9 g; 1H NMR SPeCtTUm: (DMSOd6) 1.68 (s, 6H), 7.44 (m, IH), 7.61 (d, IH), 8.1 (d, IH), 8.52 (2s, IH), 8.66 (s, IH), 11.15 (br s, IH); Mass Spectrum: M-H” 263.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15568-85-1, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); 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. 193290-19-6, name is Methyl 2-(4-bromo-2-fluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-(4-bromo-2-fluorophenyl)acetate

A suspension of methyl (4-bromo-2-fluorophenyl)acetate (5.5 g, 0.0223 mol; see step (v) above), Zn(CN)2 (1.79 g, 0.0156 mol) in dry DMF (30 mL) was purged with argon for 15 minutes before Pd(PPh3)4 (1.27 g, 0.0011 mol) was added. The resulting suspension was stirred at 800C overnight under a nitrogen atmosphere before the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by purification over silica gel (using 18% ethyl acetate in petroleum ether as eluent) gave the sub-title compound (3.6 g) as a pale yellow solid.

According to the analysis of related databases, 193290-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/69986; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1678-68-8, name is trans-Ethyl 4-aminocyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of trans-Ethyl 4-aminocyclohexanecarboxylate

Ethyl trans-4-aminocyclohexanecarboxylate (J. Med. Chem., 1971, 14, 600-614) (29.5 g, 143 mmol) was dissolved in 1,4-dioxane (290 ml) and water (290 ml), triethylamine (30.0 ml, 215 mmol) and 1-[2-(trimethylsilyl)ethoxycarbonyloxy]pyrrolidine-2,5-dione (40.8 g, 157 mmol) were added under ice cooling and the resulting mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated and then the residue was diluted with ethyl acetate and washed with 10% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine in that order. The organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure to give 44.3 g (98%) of the title compound as colorless needle-like crystals.1H-NMR (500 MHz, CDCl3) delta: 0.03 (9H, s), 0.92-1.01 (2H, m), 1.08-1.18 (2H, m), 1.25 (3H, t, J=7.2 Hz), 1.48-1.59 (2H, m), 1.97-2.11 (4H, m), 2.21 (1H, tt, J=12.3, 3.7 Hz), 3.38-3.54 (1H, m), 4.07-4.19 (4H, m), 4.38-4.49 (1H, m).

The synthetic route of 1678-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugimoto, Yuuichi; Uoto, Kouichi; Wakabayashi, Takanori; Miyazaki, Masaki; Setoguchi, Masaki; Taniguchi, Toru; Yoshida, Keisuke; Yamaguchi, Akitake; Yoshida, Shoko; US2012/264738; (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. 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl 9-Amino-4,7-dioxanonanoate

To a solution of Z-Glu-OBz (0.5 g, 1.356 mmol) in CH2CI2 (3 mL) was added amino-DPEG2 t-buty ester (3 14 mg, 1.35 mmol), HATU (614 mg, 1.62 mmol), HO At (220 mg, 1 62 mmol) and TEA (0.563 ml, 4.04 mmol). The reaction mixture was stirred overnight at room temperature, diluted with EtOAc, and washed with brine (3x). The organic phase s dried over Na2S04, and concentrated. The crude product was purified on silica gel (ISCO, 40 g, 0-10 % MeOH / DCM eluent) to afford compound 74 (390 mg, 49.4 % yield). ESI MS: C31H42N2O9 (M+H) 587.3; found 587 3

According to the analysis of related databases, 756525-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERSANA THERAPEUTICS, INC.; THOMAS, Joshua D.; JONES, Brian D.; KELLEHER, Eugene W.; LOWINGER, Timothy B.; YANG, Liping; YIN, Mao; YURKOVETSKIY, Aleksandr V.; (397 pag.)WO2019/126691; (2019); A1;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 18595-12-5, A common heterocyclic compound, 18595-12-5, name is Methyl 5-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.

REFERENTIAL EXAMPLE 43 Production of 6-methyl-3-(1-pyrrolyl)benzyl alcohol 158 mg of methyl 3-amino-6-methylbenzoate was dissolved in 3 ml of acetic acid, and 139 mg of 2,5-dimethoxytetrahydrofuran was added. The mixture was heated under reflux for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography Wakogel C-200, 10 g; eluding solvent: hexane/ethyl acetate=10/1) to give 185 mg (yield 87%) of methyl 3-(1-pyrrolyl)-6-methylbenzoate, m.p. 56-57 C.

The synthetic route of 18595-12-5 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 443-26-5, name is Ethyl 2-fluorobenzoate, 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 443-26-5, Recommanded Product: Ethyl 2-fluorobenzoate

General procedure: A mixture of substituted ethyl benzoate 2 (10 mmol) and hydrazinehydrate (20 mmol) in ethanol was stirred at room temperaturefor 3 h and then filtered. The crude product recrystallizedfrom absolute alcohol to give 3a-l, which were used directly forthe next step. Under this same condition, the intermediate compounds 8a-d were also prepared.

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; He, Haifeng; Wang, Wei; Zhou, Yuan; Xia, Qin; Ren, Yanliang; Feng, Jiangtao; Peng, Hao; He, Hongwu; Feng, Lingling; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1879 – 1888;,
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Ester – an overview | ScienceDirect Topics

Application of 106896-49-5,Some common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, molecular formula is C8H8BrNO2, 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.

General procedure: Tert-butyl (R)-(5-(trimethylsilyl)pent-4-yn-2-yl)carbamate (160 mg, 0.63 mmol) was added in DMF (2.5 mL) to a sealed vial containing amino-halide (0.5 mmol), sodium carbonate (106 mg, 1.00 mmol), lithium chloride (21.00 mg, 0.50 mmol) and Pd(dppf)Cl2.CH2Cl2 (14.62 mg, 0.02 mmol). The reaction was degassed for 10 min, then heated to 100 C for 4 hours. After cooling, the reaction was diluted with EtOAc and washed with water and brine. The organic was dried over Na2SO4 and evaporated, then the crude product was purified by flash silica chromatography (EtOAc / heptane). Pure fractions were evaporated to dryness to afford the indole.

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moss, Thomas A.; Lister, Andrew S.; Wang, Jimmy; Tetrahedron Letters; vol. 58; 32; (2017); p. 3136 – 3138;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 179022-43-6, 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. 179022-43-6, name is Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Example 6: 8-{l-[7-(cis-4-methyl-cyclohexyloxy)-8-trifluoromethyl-naphthalen-2-yl]-ethyl}-8-aza-bi cyclo[3.2.1]octane-3-carboxylic acid To a mixture of cesium carbonate (179 mg, 0.549 mmol) and 8-aza-bicyclo[3.2.1]octane-3-carboxylic acid methyl ester; HC1 salt (113 mg, 0.549 mmol) was added solution of 7-(l-bromo-ethyl)-2-(4-methyl-cyclohexyloxy)-l-trifluoromethyl-naphthalene (152 mg, 0.366 mmol) in N,N-dimethylformamide (4 mL, 50 mmol). The reaction mixture was stirred at rt for 30min, and heated at 50 C overnight. LCMS showed fairly clean Rt = 1.61min, m/z = 504.3. The mixture was diluted with MeOH, filtered to remove solid, and purified by HPLC (TFA method) to get the ester. The above ester was dissolved in MeOH (0.5mL) and THF (0.5 mL), added lithium hydroxide (0.0104 mL, 1.10 mmol) and water (0.5 mL) stirred at 50 C (hot plate) for lh. LC-MS shows the reaction was completed. Neutralized with concentarted HC1 solution, Prep HPLC gave product as a solid (32.7 mg, 18%). LCMS: Rt = 1.54 min, m/z = 490.3. 1H NMR (400 MHz, METHANOL-d4) delta 8.30 (s, 1H), 8.15 (d, J = 9.35 Hz, 1H), 8.08 (d, J = 8.47 Hz, 1H), 7.53 – 7.66 (m, 2H), 4.91 – 5.02 (m, 1H), 4.37 – 4.60 (m, 1H), 3.39 – 3.48 (m, 1H), 2.88 – 3.04 (m, 1H), 1.34 – 2.66 (m, 21H), 0.98 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; MI, Sha; PENG, Hairuo; SHAO, Zhaohui; SUN, Lihong; TAVERAS, Arthur; WANG, Deping; XIN, Zhili; ZHANG, Lei; WO2014/18881; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 178747-79-0, name is Methyl 2-fluoro-6-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H9FO3

Reference Example 45 2-(2-Fluoro-6-methoxyphenyl)-2-propanol To a solution of methyl 2-fluoro-6-methoxybenzoate (0.92 g) in tetrahydrofuran (12.5 mL) was added methylmagnesium iodide (3.0 mol/L diethyl ether solution, 5 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane – n-hexane/ethyl acetate = 1/1) to give the title compound (0.8 g).

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 178747-79-0.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 877149-10-5, 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. 877149-10-5, name is Methyl 4-bromo-2-chloro-6-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 4-bromo-2-chloro-6-methylbenzoate (1, 2.0 g, 7.6 mmol) in carbon tetrachloride (20 ml) were added N-bromosuccinimide (1.6 g, 9.1 mmol) and 2,2?-azobis(2-methylpropionitrile) (0.25 g, 1.52 mmol). The reaction mixture was stirred at 80¡ã C. for 12 h and progress of the reaction was monitored by TLC. After completion, solvent was diluted with dichloromethane and the organic layer was washed with water and brine. Following separation, the organic layer was dried using sodium sulphate and concentrated under reduced pressure to afford methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate (2) as a yellow sticky liquid. Yield: 3.9 g, crude.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-2-chloro-6-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics