Tag: M.W=100-200

Some common heterocyclic compound, 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, molecular formula is C7H14ClNO3, 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. Safety of Ethyl 3-ethoxy-3-iminopropionate hydrochloride

The imidate salt 1g2 (1.5 g, 7.65 mmol) was combined with 2-methyl-3-aminoanisole 1ml (1.05 g, 7.65 mmol, 1 eq.) in ethanol (15 mL) under an N2 atmosphere. The reaction mixture was stirred at RT (24 h) and monitored by HPLC. The reaction mixture was concentrated and then ether was added and the mixture filtered. The solids were washed with ether and the combined ether washes concentrated in vacuo. The resulting adduct 1m2 was purified by chromatography (SiO2, 15percent EtOAc/hexanes) to obtain as a yellow oil (2.11 g, 99percent). MS electrospray: (M+H)+; 280 and (M-H)-; 278.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2318-25-4, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/19905; (2006); A1;,
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Electric Literature of 5026-62-0, 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. 5026-62-0, name is Sodium 4-(methoxycarbonyl)phenolate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The above titled compound was prepared by the Method E (ArXBC(R10R11): (4-carboxyphenoxy)methyl). R. Compound A (100 mg) was placed in a 8.0 mL, polypropylene filter column fitted with a 2-way polypropylene stopcock. The resin was pretreated with CH2Cl2 (2 x 3 mL). The swollen resin was then deprotected with 50% TFA/CH2Cl2 (3mL, 30min). The resin was rinsed in the following order: CH2Cl2 (2 x 3 mL), CH3OH (2 x 3 mL), CH2Cl2 (2 x 3 mL). Bromoacetic acid (85 mg) and diisopropyl-carbodiimide (80 mg) in DMF (2.0 mL) was added and the mixture was stirred for 1 hr at room temperature. The resin was filtered and washed in the following order: DMF (2 x 3 mL), CH2Cl2 (2 x 3 mL), DMF (2 x 3 mL), respectively. If a Kaiser test on a small quantity of the resin is positive (blue) then ‘repeat the’ coupling procedure until a negative result is obtained. Methyl p-hydroxybenzoate (91 mg) was pretreated with NaH (20 mg) in THF (0.5 mL) and DMF (2 mL) for 1.5 hr. The resulting phenoxide was added to the resin and the mixture was stirred for 2 hr at room temperature. The resin was then filtered and washed in the following order: DMF (2 x 3 mL), CH2Cl2 (2 x 3 mL), THF (2 x 3 mL), respectively. The resulting resin was then dried in vacuum to constant weight. The cleavage of the resin (saponification) was achieved with LiOH/CH3OH/THF (1:6:20). The resin bound material was placed in the polypropylene column and pretreated with THF (3 mL). Then THF (4 mL), CH3OH (1.0 mL) and 2N LiOH (0.390 mL) were added. The mixture was stirred for 15 min and filtered to a clean and pre weighed test tube. The resin was next washed with THF/5% CH3OH (2mL) and the combined filtrates were evaporated. The resulting gum was dissolved in H2O (1 mL). The solution was then acidified with 1N HCl to pH 2.0. The precipitate was centrifuged, washed with water (2 x 5 mL) and dried in vacuum to furnish the compound of Example 12: ESMS (m/z) 529 (M-H)-

The synthetic route of Sodium 4-(methoxycarbonyl)phenolate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1144365; (2004); B1;,
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Reference of 61367-07-5,Some common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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.

A stirred solution of 6-(5-cyano-1H-pyrazolo[3,4-b]pyridin-1-yl)-4-(cyclopropylamino)nicotinic acid (0.3 g, 0.94 mmol, Intermediate L), methyl (1R,4R)-4-aminocyclohexane-1-carboxylate hydrochloride (0.18 g, 0.94 mmol), HATU (0.54 g, 1.41 mmol) and DIPEA (0.54 mL, 1.41 mmol) in DMF (5 mL) was stirred at rt for 4 h. The reaction mixture was transferred then into ice water and the resulting precipitate was filtered off and dried under vacuum to give methyl (1R,4R)-4-(6-(5-cyano-1H-pyrazolo[3,4-b]pyridin-1-yl)-4-(cyclopropylamino)nicotinamido)cyclohexane-1-carboxylate as an off white solid (0.38 g, 88%). LC-MS (ESI+) m/z 460.2 (

The synthetic route of 61367-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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Synthetic Route of 73792-08-2, 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. 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 7Synthesis of 2-cyano-3-(2-fluoro-4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)-dimethylacrylamideStep 1To a 250 ml three necked round bottom flask, methyl 4-amino-2-fluorobenzoate (2.75 g, 0.0162 mole) was added in anhydrous THF (60 ml) under nitrogen atmosphere and cooled to 0- 5 C. After 15 minutes, 2.0 M solutions of LAH in THF (24.3 ml, 0.0487 mole) was added dropwise and stirred for 10 min. The reaction mixture was allowed to warm up to room temperature and stirred at same temperature for 1 hr. After completion of the reaction, the reaction mixture was cooled to 5 C and quenched with sat. NH4C1 (25 ml) and diluted with water (100 ml) followed by extraction with ethyl acetate. The combined organics were washed with water, dried over sodium sulphate and evaporated to afford brown solid (crude) product which was purified using column purification by eluting the compound with 20% ethyl acetate in hexanes to yield 1.7 g of (4-amino-2-fluorophenyl)methanol.

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

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 3,4-diaminobenzoate

General procedure: A mixture of o-phenylenediamine (1.0 mmol), aryl aldehyde(1.0 mmol) and chromium(III) salen complex nanoparticles supported on AlPO4(2.0 mol%) in ethanol (5 mL) was stirred at room temperature. After completion of the reaction (TLC), the mixture was centrifuged and rinsed with ethanol (3 ¡Á 15 mL). The recovered nanocatalyst was dried and stored for another consecutive runs. The solvent was evaporated to give the crude product, which was purified by silica gel column chromatography employing n-hexane/ethyl acetate (8:1) as eluent.

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 37466-90-3.

Reference:
Article; Sharghi, Hashem; Aberi, Mahdi; Doroodmand, Mohammad Mahdi; Shiri, Pezhman; Journal of the Iranian Chemical Society; vol. 14; 7; (2017); p. 1557 – 1573;,
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Synthetic Route of 18358-63-9, 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. 18358-63-9, name is Methyl 4-(methylamino)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4.13 Lithium 4-[methyl(phenylsulfonyl)amino1benzoate; To a mixture of methyl 4-(methylamino)benzoate (1 mmol), 4-dimethylaminopyridine (2 mg), and diisopropylethylamine (1.1 mmol) in acetonitrile (3 ml) was added benzenesulfonyl chloride (1.1 mmol). The reaction mixture was stirred for 16h, and the mixture concentrated by nitrogen stream. The crude product was partitioned between 1 M HCI (aq) and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with 1 M HCI (aq), water, brine and dried over sodium sulfate. The solvent was removed and the crude product was purified by flash column chromatography on silica to give methyl 4- [methyl(phenylsulfonyl)amino]benzoate as a white solid (249 mg, 81 %).

The synthetic route of Methyl 4-(methylamino)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; WO2007/144379; (2007); 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 3618-04-0

(1) Synthesis of ethyl 4-((tert-butyl(diphenyl)silyl)oxy)cyclohexanecarboxylate To a solution of 25 g of 4-hydroxycyclohexanecarboxylic acid in 125 ml of N,N-dimethylformamide were sequentially added 21.7 g of imidazole and 39.6 ml of tert-butyl (diphenyl)silyl chloride under cooling with ice, followed by stirring the reaction mixture at room temperature for 3 hours. To the reaction mixture was added water and extracted with hexane. The resulting hexane solution was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound.

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; Iwasawa, Yoshikuzu; Kato, Tetsuya; Kawanishi, Nobuhiko; Masutani, Kouta; Mita, Takashi; Nonoshita, Katsumasa; Ohkubo, Mitsuru; US2008/58347; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 61367-07-5, 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. 61367-07-5 name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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.

A mixture of 1.5 g (7.745 mmol) of methyl frans-4-aminocyclabexanecarboxyiate hydrochloride, 4 mL (46.5 mmol) of 2-fiuoropyridine and 1.35 mL (7.75 mmol) of DIPEA was stirred at 125 C in a pressure-resistant glass reactor for 20 hours, then cooled to room temperature. The reaction mixture was diluted with 20 mL of ethyl acetate, washed with 2×30 mL of water and saturated NaCI solution, the organic phase was dried over anhydrous Na2S04, filtered and concentrated to yield 325 mg (18%) of the title compound. MS (ESI) m/z 235.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; BATA, Imre; SZELECZKY, Zsolt; SZONDINE KORDAS, Krisztina; SZANTO, Gabor; (191 pag.)WO2019/116325; (2019); A1;,
Ester – Wikipedia,
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Electric Literature of 4630-80-2, 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. 4630-80-2, name is Methyl cyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of sodium hydride (1.87 g, 55% in mineral oil, 42.9 mmol) in THF (10 ml) was added a solution of methyl cyclopentanecarboxylate (5 g, 39.0 mmol) and acetonitrile (1.92 g, 2.45 ml, 46.8 mmol) in THF (3 ml) dropwise at 70C. The mixture was heated to 70C overnight, then cooled to room temperature, diluted with IN HCl and extracted with EtOAc. The combined organic layers were washed with water and brine, dried with Na2S04 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 95:5 – 85: 15) to afford the title compound (4105 mg, 77%) as light yellow liquid.

The chemical industry reduces the impact on the environment during synthesis Methyl cyclopentanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RUDOLPH, Markus; WO2013/64465; (2013); A1;,
Ester – Wikipedia,
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Synthetic Route of 3377-20-6,Some common heterocyclic compound, 3377-20-6, name is Diethyl 2-methylenemalonate, molecular formula is C8H12O4, 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.

nBuLi solution (2.5 M in hexanes, 2.5 mL, 6.2 mmol) was added, dropwise over 3 min., to a cooled (dry ice/EtOH/ethylene glycol bath at .20 C) solution of N,N,N?-trimethylethylenediamine (0.90 mL,6.9 mmol) in 2-MeTHF (15 mL). After stirring for 20 min., 2- chlorobenzaldehyde (0.70 mL, 6.2 mmol) was added dropwise, maintaining the internal reaction temperature below .20 C. After 10 min., more nBuLi solution (2.5 M in hexanes, 7.6 mL, 19 mmol) was added dropwise, again maintaining the internal reaction temperature below .20 C. After stirring at this temperature for 2.5 h, the reaction mixture was cooled in a dry ice/acetone bath. Diethyl ketomalonate (4.1 mL, 27 mmol) was added to the reaction mixture dropwise, maintaining the internal reaction temperature below .50 C. After 5 min., the reaction was quenched by rapid addition of aq. HCl (1.0 M, excess), and cooling was ended. The resulting mixture was extracted with dichloromethane (2x), and the combined organic layers were dried (sodium sulfate) and evaporated to afford a clear, orange oil. Repeated chromatographic purification (48 g silica gel, 1:19 to 1:1 EtOAc/heptane gradient; then 48 g silica gel, 1:9 to 2:3 EtOAc/heptane gradient; and finally 54 g silica gel, 1:9 dichloromethane/heptane to dichloromethane to 1:19 EtOAc/dichloromethane gradient) afforded the title compound as a clear, colorless oil (224 mg, 11 % yield). GCMS (EI) m/z: 314 [M+] (6.2 %). 1H NMR (400 MHz, CDCl3) ? 1.28 (t, J = 7.1 Hz, 3H), 1.31 (t, J = 7.1 Hz, 3H), 2.92 (s, 1H), 4.23 (dq, J = 10.8, 7.1 Hz, 1H), 4.30 (dq, J = 10.8, 7.1 Hz, 1H), 4.32 (dq, J = 10.7, 7.1 Hz, 1H), 4.36 (dq, J = 10.7, 7.1 Hz, 1H), 6.00 (s, 1H), 6.90 (d, J = 8.2 Hz, 1H), 6.96 (d, J = 7.9 Hz, 1H), 7.22 (t, J = 8.1 Hz, 1H).

The synthetic route of 3377-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rocke, Benjamin N.; Conn, Edward L.; Eisenbeis, Shane A.; Ruggeri, Roger B.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5467 – 5470;,
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