Category: esters-buliding-blocks

Application of 21597-54-6, The chemical industry reduces the impact on the environment during synthesis 21597-54-6, name is Methyl 3-amino-2-naphthoate, I believe this compound will play a more active role in future production and life.

40 g of compound A-1 (264 mmol) was added to a 500 ml three-necked flask, 16 g of formic acid and 160 ml of formamide were added, and the mixture was heated to 135 C for 5 h, and the reaction of the raw materials was completed by TLC; 200 ml of water was added, and the mixture was kept at 20 to 30 C for 1 h, and filtered. The filter cake was rinsed with water and recrystallized from ethanol to give 36.4 g of Compound A-2, yield 93.1%, purity 98.2%.

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 3-amino-2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yantai Jiu Mu Chemicals Co., Ltd.; Song Sisi; Chen Muxin; Li Xiangyang; Kong Xiangxing; Cui Lisha; (32 pag.)CN108178750; (2018); A;,
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96999-01-8, name is Methyl 1-bromocyclopropanecarboxylate, 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. Computed Properties of C5H7BrO2

A mixture of 12j (2.40 g, 10 mmol), 3a-3b (15 mmol) andCs2CO3 (9.77 g, 30 mmol) in DMF (50 mL) was stirred at 90 C(for 3a) or 120 C (for 3b) in N2 atmosphere until the completion of reaction as indicated by TLC (typically within 12 h). Oncooling to room temperature, the reaction mixture was pouredinto ice-water (200 mL), and the mixture thus obtained wasextracted with CH2Cl2 (3 ¡Á 100 mL). The combined extractswere washed with 5% brine (5 ¡Á 100 mL), dried over anhydrous Na2SO4 and evaporated on a rotary evaporator to aord aresidue, which was purifed by column chromatography to yield21a-21b after trituration with EtOAc/n-hexane.6-Bromo-4-methylthioquinoline (21a). 1.07 g (42%). Whitesolid, m.p. 88-90 C. 1H NMR, delta 8.75 (d, J = 4.8 Hz, 1H),8.14 (d, J = 1.6 Hz, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.90 (dd,J = 2.0 Hz and 9.2 Hz, 1H), 7.40 (d, J = 4.8 Hz, 1H), 2.66(s, 3H). 13C NMR, delta 149.97, 146.97, 145.21, 132.71, 131.85,126.63, 124.88, 119.56, 116.27, 13.37. ESI-HR-MS, calcd. forC10H9BrNS ([M(79Br)+H]+) 253.9639, found 253.9641; calcd.for C10H9BrNS ([M(81Br)+H]+) 255.9619, found 255.9628.

The synthetic route of 96999-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Yuqiang; Xie, Yafei; Liu, Changying; Wang, Jianwu; Zhao, Guilong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 7; (2017); p. 799 – 811;,
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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;,
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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. 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;,
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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;,
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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;,
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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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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;,
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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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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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