Tag: M.W=100-200

Reference of 6276-54-6, A common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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.

Add 750 g of dimethyl sulfoxide to the reaction flask.420 g (2.196 mol) of compound 1 (prepared in Example 3) are added,Add 340g (8.5mol) of sodium hydroxide, heat, raise the temperature to about 90 C, add 14g of potassium iodide,Under stirring, 340 g (2.615 mol) of 3-chloropropylamine hydrochloride was added in portions, and the reaction was incubated at 100-110 C. for 20 hr.After confirmation of the reaction, 1000 g of water was added, pH=10~11 was adjusted with concentrated hydrochloric acid, and the mixture was stirred for about 1.5 hr. The mixture was allowed to stand for liquid separation. The aqueous phase was extracted once with 800 g of toluene. The organic phase was combined and used 50 kg of sodium chloride. The aqueous solution was washed once, and the liquid was separated. The organic solvent was concentrated and the solvent was weighed to obtain 500 g of an oil (theoretical amount: 545.38 g). Yield: 91.7%.

The synthetic route of 6276-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Inner Mongolia Jingdong Pharmaceutical Co., LTD.; Guo, Rong Yao; Wang, Xiao Feng; Inner Mongolia Jingdong Pharmaceutical Co., Ltd.; Guo Rongyao; Wang Xiaofeng; (11 pag.)CN107698538; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 2106-02-7, name is 2-Chloro-4-fluoroaniline, belongs to chlorides-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 2106-02-7, Product Details of 2106-02-7

[3452] A solution of 2-chloro-4-fluoroaniline ( 1.000 g, 6.870 mmol), methyl 4-(bromomethyl)-3-fluorobenzoate ( 1.867 g, 7.557 mmol) and potassium carbonate ( 1.899 g, 13.740 mmol) in acetonitrile ( 10 mL) was stirred at the room temperature for 15 hr, filtered to remove solids, and concentrated under the reduced pressure. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / hexane = 0 % to 10 %) to give methyl 4-(((2-chloro-4-fluorophenyl)amino)methyl)-3-fluorobenzoate as green solid (0.974 g, 45.5 %).

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, 2-Chloro-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
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Synthetic Route of 13078-79-0,Some common heterocyclic compound, 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, molecular formula is C8H10ClN, 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: A mixture of 26 (100mg, 0.27mmol), 4-tolylmethanamine (100mg, 0.08mL, 0.81mmol), BOP reagent (120mg, 0.27mmol), and triethylamine (80mg, 0.11mL, 0.81mmol) in anhydrous DMF (5mL) was stirred at 25C for 12h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and filtered. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, ethyl acetate:n-hexane=1:2 as eluent) to furnish 4 (70mg, 56%), mp 240-242C (from ethanol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Chlorophenyl)ethanamine, its application will become more common.

Reference:
Article; Famiglini, Valeria; La Regina, Giuseppe; Coluccia, Antonio; Pelliccia, Sveva; Brancale, Andrea; Maga, Giovanni; Crespan, Emmanuele; Badia, Roger; Clotet, Bonaventura; Este, Jose A.; Cirilli, Roberto; Novellino, Ettore; Silvestri, Romano; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 101 – 111;,
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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. 4152-90-3, name is (3-Chlorophenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of (3-Chlorophenyl)methanamine

STEP7 Preparation of N-(3-chlorobenzyl)-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine A mixture of 8-chloro-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazine (500 mg, 1.60 mmol), (3-chlorophenyl)methanamine (0.236 mL, 1.92 mmol) and DIPEA (0.700 mL, 4.01 mmol) in i-BuOH (8.0 mL) was subjected to microwave irradiation at 170° C. for 4 h. (The reaction was repeated 4 times in same scale). The combined reaction mixture was cooled to room temperature, diluted with EtOAc and washed with water and brine. The separated organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on NH-SiO2 (Hexanes:EtOAc=1:1) to give N-(3-chlorobenzyl)-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine (2.40 g, 90percent) as a yellow oil. 1H-NMR (CDCl3, 400 MHz): delta 7.44 (d, J=4.8 Hz, 1H), 7.39-7.40 (m, 2H), 7.26-7.25 (m, 4H), 6.32-6.24 (m, 1H), 5.10-5.05 (m, 2H), 4.78 (d, J=6.4 Hz, 2H), 4.55 (s, 1H), 3.05-3.04 (m, 2H), 1.60 (s, 3H), 1.38 (s, 3H).

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANDOK INC.; Lee, Jin-Hwa; Kim, Seung-Yong; Kim, Do-Ran; Ahn, Koo-Hyeon; Lee, Gwi-Bin; Kim, Doo-Seop; Hwang, Hyun-Sook; (74 pag.)US2017/204101; (2017); 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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H17Cl2N

General procedure: Commercially available 5-chloro benzoxazoles or benzothiazoles(5 mmol) and K2CO3 (15 mmol) were added to 50 mL of DMF.The mixture was heated at 60 C and 1-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (6.5 mmol) was added. The mixture was maintained at 60 C under stirring for 3 h, then was cooled to room temperature, poured into water, and extracted with diethyl ether(3 50 mL). The organic layer was washed with brine, dried overan hydrous Na2SO4 and evaporated under reduced pressure to give are sidue, which was purified by flash column chromatography oversilica gel using ethyl acetate/methanol 8:2 v/v as eluent. Immediately after solvent evaporation, free bases were converted into hydrochlorides by dissolving the corresponding amine in diethyl ether and treating with a 1.25MHCl ethanol solution (pH 1e2). The precipitate was filtered off, washed with diethyl ether, and dried under nitrogen. The following compounds were obtained using this procedure:

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romeo, Giuseppe; Prezzavento, Orazio; Intagliata, Sebastiano; Pittala, Valeria; Modica, Maria N.; Marrazzo, Agostino; Turnaturi, Rita; Parenti, Carmela; Chiechio, Santina; Arena, Emanuela; Campisi, Agata; Sposito, Giovanni; Salerno, Loredana; European Journal of Medicinal Chemistry; vol. 174; (2019); p. 226 – 235;,
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7149-75-9, name is 4-Chloro-3-methylaniline, belongs to chlorides-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. name: 4-Chloro-3-methylaniline

Step 1 (0443) To a mixture of 3-iodo-4-methylbenzaldehyde (600 mg), 4-chloro-3-methylphenylamine (414 mg), tetrahydrofuran (2 mL) and methanol (6 mL) was added decaborane (90 mg), and the mixture was stirred at room temperature for 1 hour. After the mixture was diluted with ethyl acetate, to the resulting mixture was added aminopropyl silica gel powder (3 g). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to give (4-chloro-3-methylphenyl)-(3-iodo-4-methylbenzyl)amine (900 mg).

The synthetic route of 7149-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); A1;,
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Application of 108-41-8, A common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, 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: Under N2 atmosphere, NHC-Pd(II)-Im complex 1 (6.5 mg,1.0 mol%), KOtBu (224.4 mg, 2.0 mmol), toluene (1.0 mL), ketones 3 (2.0 mmol or 0.7 mmol), and aryl chlorides 2 (1.0 mmol) were successively added into a Schlenk reaction tube. The mixture was stirred at the specified temperature for the listed time shown inTables 1-3. The reaction mixture was cooled to room temperature,then the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography to give the pure products.

The synthetic route of 108-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xiao, Zheng-Kang; Yin, Hui-Ying; Lu, Jian-Mei; Inorganica Chimica Acta; PA; (2014); p. 106 – 108;,
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Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, belongs to chlorides-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 4584-46-7, Safety of 2-Chloro-N,N-dimethylethanamine hydrochloride

N,N-Dimethyl-2-(5-nitroindolin-1-yl)ethanamine (2) A solution of compound 1 (500 mg, 3.05 mmol) in DMF (10 mL) was treated with NaH (390 mg, 9.75 mmol, 60% wt in mineral oil) at 0 C. resulting in an orange mixture. It was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (877 mg, 6.09 mmol) resulting in a dark red mixture. The reaction was heated to 90 C. and stirred for 1.5 hours. After allowing the reaction to cool to room temperature, water (80 mL) was added, and the reaction was extracted into ethyl acetate (3*25 mL). The combined organic layers were washed with water (2*15 mL) and then with brine (10 mL), dried (Na2SO4), filtered, and concentrated. The residue was subjected to flash chromatography on silica gel:CH2Cl2 and then 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 to give a brownish/red solid (400 mg, 56% yield). 1H-NMR (DMSO-d6) delta 7.96 (dd, J=2.1, 8.7 Hz, 1H), 7.79 (d, J=2.1 Hz, 1H), 6.49 (d, J=9.0 Hz, 1H), 3.72 (t, J=8.7 Hz, 2H), 3.39 (t, J=6.6 Hz, 2H), 3.04 (t, J=8.7 Hz, 2H), 2.44 (t, J=6.3, 2H), 2.18 (s, 6H).

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; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
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Related Products of 2533-69-9, A common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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.

Step 1. Synthesis of 3-(4-chloro-3-fluorophenyl)-2-(trichloromethyl)-3H-imidazo[4,5-b]pyridine (C20) Methyl 2,2,2-trichloroethanimidoate (0.743 mL, 6.00 mmol) was added to a solution of N2-(4-chloro-3-fluorophenyl)pyridine-2,3-diamine (C12) (951 mg, 4.00 mmol) in acetic acid (4 mL), and the reaction mixture was stirred at room temperature for 5 hours. After concentration in vacuo, the residue was purified via chromatography on silica gel (Gradient: 5% to 100% ethyl acetate in heptane) to afford the product as a white solid. Yield: 1.04 g, 2.85 mmol, 71%. LCMS m/z 366.0 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.49 (dd, J=4.7, 1.5 Hz, 1H), 8.27 (dd, J=8.1, 1.5 Hz, 1H), 7.64 (ddd, J=8.5, 7.8, 0.3 Hz, 1H), 7.42 (dd, J=8.1, 4.7 Hz, 1H), 7.39 (ddd, J=8.8, 2.4, 0.2 Hz, 1H), 7.32 (ddd, J=8.5, 2.4, 1.3 Hz, 1H).

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chappie, Thomas Allen; Verhoest, Patrick Robert; Patel, Nandini Chaturbhai; Hayward, Matthew Merrill; US2014/235612; (2014); A1;,
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Application of 33050-38-3, A common heterocyclic compound, 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, molecular formula is C5H2Cl2N4, 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.

b) The 3-chloro-6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazine can be prepared in the following way:0.9 cm3 of morpholine and 1.4 cm3 of triethylamine are added to a solution of 1.89 g of commercial 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine in 20 cm3 of N,N-dimethylformamide. The reaction is stirred at 20 C. for 19 1H). 60 cm3 of water are added and the mixture is extracted with ethyl acetate. The organic phase is washed with water and with brine and then dried over magnesium sulphate and concentrated to dryness, to give a beige solid. The latter is chromatographed by solid deposit on a Merck cartridge of 70 g of silica 15-40 mum, elution being carried out with a gradient of 100% dichloromethane to 95/5 dichloromethane/methanol. 1.97 g of 3-chloro-6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazine are obtained in the form of a very pale yellow solid, the characteristics of which are as follows:MASS SPECTRUM: UPLC-MS-DAD-ELSD: 240=MH+.

The synthetic route of 33050-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; sanofi-aventis; US2010/298315; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics