Month: December 2020

136-90-3,Some common heterocyclic compound, 136-90-3, name is 4-Methoxy-3-methylphenylamine, molecular formula is C8H11NO, 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.

c) 2-Hvdroxyimino-Lambda/-(4-methoxy-3-methylphenyl)acetamideChloral hydrate (11.5 g, 70 mmol) and anhydrous sodium sulfate (60 g, 422 mmol) were added to vigorously stirred water (300 ml_). A slurry prepared by mixing hydroxylamine5 hydrochloride (23.0 g, 331 mmol) and 4-methoxy-3-methylphenylamine (10.0 g, 73 mmol) with aqueous hydrochloric acid (2.4 M, 250 ml.) was added to the above mixture. The resulting mixture was refluxed for 20 min and then allowed to stand at room temperature for 16 h. A precipitate formed and was collected by filtration. The solid was washed with water and dried to yield 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide (6.7 g,10 32 mmol, 44%)Data for 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide: MS (ESI) m/z: 209 ([M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methoxy-3-methylphenylamine, its application will become more common.

Reference:
Patent; AKZO NOBEL N.V.; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/95014; (2006); A1;,
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446-59-3, A common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, molecular formula is C7H6BrFO, 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.

General procedure: The 2-bromo-1-ethoxy-4-fluoro-benzene (0.1 mol) was dissolved in THF (25 ml). The solution was cooled to -75 C and a solution of n-BuLi (9.73 ml, 2.4 M in hexane) was added slowly. The mixture was stirred for 30 min at -75 C. Trimethylborate (0.1 mol) was added within 5 min. Acetic acid (0.1 mol) and a 30% solution of H2O2 (0.1 mol) were added sequentially. The mixture was stirred for 30 min at 0 C and for 3 h at room temperature. Water was added and the mixture was extracted with ethyl acetate. The crude product was purified by column chromatography to yield the objected compound.

The synthetic route of 446-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Heng; Xu, Xiangqing; Chen, Yin; Qiu, Yinli; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen; European Journal of Medicinal Chemistry; vol. 89; (2015); p. 524 – 539;,
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A common compound: 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 126-38-5

To a mixture of 3-bromobenzenethiol (8.7 g, 46 mmol) and l -bromo-2,2- dimethoxypropane (8.4 g, 46 mmol) in NN-dimethylformamide (50 mL) was added potassium carbonate (9.5 g, 69 mmol) at room temperature. The mixture was stirred at 80 C overnight. On completion, the reaction mixture was quenched with water and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude compound B-287 (13 g, 97% yield) as a colorless oil.

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, 126-38-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
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The chemical industry reduces the impact on the environment during synthesis 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, I believe this compound will play a more active role in future production and life. 14869-41-1

To a suspension of compound 26-5 (0 1 g) and 2-chloroethoxy acetic acid (45 4 mg) m DMF (2 mL), was added4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholmium chloride (DMT-MM, 87 7 mg) The reaction mixture was stirred at room temperature overnight Then, according to the Step 29-1 in synthetic method for EXAMPLE 29, cychzation reaction was pursued to obtain compound 30-1 (90 mg) as a colorless amorphous solid

The chemical industry reduces the impact on the environment during synthesis 14869-41-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; SCHERING CORPORATION; NISHIDA, Hidemitsu; SAITOH, Fumihiko; HIRABAYASHI, Tomokazu; CHACKALAMANNIL, Samuel; CHAN, Tin-Yau; CHELLIAH, Mariappan, V.; CLASBY, Martin, C.; DWYER, Michael, P.; GREENLEE, William, J.; XIA, Yan; WO2010/65717; (2010); A1;,
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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-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. 1462-37-9

After flushing the interior of the vessel with nitrogen, under nitrogen, 8.41 g (210 mmol) of sodium hydride (oily) and 80 ml of dry tetrahydrofuran were added to a 1000 ml four-necked flask, and while cooling with an ice-water bath, 34.00 g (100 mmol) in 350 ml of tetrahydrofuran was added dropwise. Immediately after the dropwise addition of DCMI in tetrahydrofuran solution, bubbles that appeared to be H 2 were observed. After foaming subsided, the temperature was raised to room temperature and stirred for 1 hour. Thereafter, while cooling the flask again with an ice-water bath, a solution of 50.01 g (233 mmol) of benzyl-2-bromoethyl ether dissolved in 50 ml of dry THF was added dropwise. After the dropwise addition, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes, then heated to 60 to 70 ¡ã C. and stirred for 18 hours. On the way, heating was stopped when benzyl-2-bromoethyl ether became a trace amount and consumption ceased almost at a time-dependent change by TLC.As a post-treatment, the flask was cooled with ice with stirring under nitrogen, 150 ml of ethyl acetate was added to the flask, then 100 ml of water was slowly added dropwise, the aqueous phase was separated off and the organic phase was washed with 100 ml of water For 2 times. The organic phase was concentrated with an evaporator to obtain 68.10 g of a viscous liquid with a yellowish tinge. Thereafter, silica gel column purification was carried out using a mixed solvent of hexane and ethyl acetate (hexane / ethyl acetate = 10/1 to 1/1 (volume ratio)), and the solvent was distilled off under reduced pressure to give the following compound 6 46.36 g (76.2 mmol: yield 76.2percent) was obtained as a viscous liquid.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; Machine: Mitsubishi ChemicalsCo ., Ltd .; Imai Nao Akira; Saito Yasuyo; Kawakami Kotoku; Fuji Tsuu Akira; (94 pag.)JP2017/222625; (2017); A;,
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These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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. 111-95-5

To the product from step 2 (1.00 g, 5.29 mmol) in ACN (20 mL) was added bis(2-methoxyethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and the reaction mixture was heated to 70 C. for 16 hours thereafter. The reaction was cooled and concentrated. The residue was partitioned with EtOAc and water. The organic layer was separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (SiO2, 10/1 hexanes-EtOAc to 1/1) afforded 950 mg (63% yield) of the desired adduct as a yellow solid: 1NMR (300 MHz, CDCl3) delta 7.47 (bs, 2H), 3.77 (t, J=5.7 Hz, 4H), 3.52 (t, J=5.4 Hz, 4H), 3.25 (s, 6H). 13C NMR (75 MHz, CDCl3) delta 154.7 (s), 152.0 (s), 120.9 (s), 119.5 (s), 95.8 (s), 71.0 (t), 59.1 (q), 50.0 (t).

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 111-95-5.

Reference:
Patent; MediBeacon Inc.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (52 pag.)US2019/125902; (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. 41406-00-2, name is 3-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 41406-00-2

EXAMPLE 178 4-(3-Isopropoxyanilino)-6-methyl-2-(2-pyridinyl)pyrimidine The title compound was prepared from 4-chloro-6-methyl-2-(2-pyridinyl)pyrimidine (82.3 mg, 0.4 mmol) and 3-isopropoxyaniline (60.4 mg, 0.4 mmol) similar to Example 173 and was isolated as a white solid (88 mg, 69%). 1H NMR (CDCl3): 8.64 (d, J=4.2 Hz, 1H), 8.35 (d, J=8.1 Hz, 1H), 7.7 (t, J=8.1 Hz, 1H), 7.24 (m, 1H), 7.15 (m, 1H), 6.96 (s, 1H), 6.76 (m, 2H), 6.60 (d, J=8.1 Hz, 1H), 6.18 (m, 1H), 4.45 (m, 1H), 2.37 (s, 3H), 1.25 (d, J=6.0 Hz, 6H).

The synthetic route of 41406-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., 22236-10-8

Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 4- (difluoromethoxy)benzenamine (10 g, 62.8 mmol), ACN (100 mL), and BS (5.59 g, 31.4 mmol). The resulting solution was stirred for 1 h RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :20 to 1 : 10). This resulted in 7.9 g (53%) of the title compound as red oil. MS-ESI: 238.0/240.0 (M+l).

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; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, belongs to ethers-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 1535-73-5, 1535-73-5

Ethyl 6-((3-(trifluoromethoxy)phenyl)carbamoyl)nicotinate (5.5.2)To a stirring solution of 5-(ethoxycarbonyl)picolinic acid (0.50 g, 2.56 mmol) in DMF (10 ml) was added CDI (0.623 g, 3.84 mmol). The reaction was allowed to stir for 10 min and the 3-(trifluoromethoxy)aniline (0.41 ml, 3.07 mmol) was added. The solution was stirred overnight at room temperature. An LC-MS was obtained which indicated the presence of the product. Water was added to the reaction and the white precipitate was filtered. LC- MS of the solid confirmed the product as ethyl 6-((3- (trifluoromethoxy)phenyl)carbamoyl)nicotinate (0.45 g, 50 percent). 1 H NMR (400MHz CDCI3) deltaEta ppm 1 .36 (t, 3H), 4.39 (q, 2H), 7.13 (d, 1 H), 7.50 (t, 1 H), 7.94 (d, 1 H), 8.09 (s, 1 H), 8.29 (d, 1 H), 8.44 (d, 1 H), 9.19 (s, 1 H), 1 1 .1 1 (s, 1 H).

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, 3-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ITHEMBA PHARMACEUTICALS (PROPRIETARY) LIMITED; MUSONDA, Chitalu, Christopher; EDLIN, Christopher, David; BOYLE, Grant, Alexander; WO2013/72903; (2013); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 60792-79-2 as follows. 60792-79-2

Example 3 Preparation of 2-hydroxy-N-(2-(2-(2-((2Z,5Z,8Z,11Z,14Z,17Z)-eicosa-2,5,8,11,14,17-hexaenylthio)acetamido)ethoxy)ethyl)benzamide (1-1) In a typical run, sodium hydroxide (400 mg, 10 mmol) is dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) is added. The resulting reaction mixture is stirred at room temperature for 30 min. A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) is then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture is stirred at room temperature for 18 h and then concentrated under reduced pressure. The resulting residue is taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture is filtered and the filtrate is concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate (850 mg, 74%).

According to the analysis of related databases, 60792-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82120; (2011); A1;,
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