Tag: M.W=200-300

Electric Literature of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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.

Example 6 4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-6-nitro-quinazoline In a flask equipped with a reflux condenser, 6-nitro-4-chloro-quinazoline 1.20g (5.7mmol) and 4-(3-fluorobenzyloxy)-3-chloroaniline 1.37g (5.6mmol) were dissolved into 80mL of isopropanol, and the solution was refluxed for 3h. Then a lot of yellow solid was deposited, which was filtered, dried under vacuum, and identified as the title compound. Yield: 67%. 1H-NMR (400MHz, CDCl3): delta11.30(1H, br), 9.54-9.48(1H, m), 8.45-8.41(1H, m), 8.31-8.25(1H, m), 7.98-7.89(1H, m), 7.50-7.47(1H, m), 7.35-7.26 (1H, m), 7.05-6.96(1H, m), 6.90-6.80(2H, m), 7.74-7.60(2H, m), 4.84(2H, s).

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; SHANGHAI ALLIST PHARMACEUTICAL., INC.; EP1990337; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6529-53-9, 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 6529-53-9 as follows.

Step D: Preparation of 6-chloro-2-[2-(4-chlorophenyl)ethoxy]-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine To a solution of crude 6-chloro-2-hydroxy-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-purine (44.0 g, ca 100 mmoles), dissolved in glass distilled dimethylformamide (2 Liters), is added 2-(4-chlorophenyl)ethyl bromide (43.6 g, 200 mmoles), followed by cesium carbonate (100 g, 307 mmoles). The mixture is stirred at room temperature for 24 hours, evaporated to dryness (TBath<50 C.), and the residue partitioned between dichloromethane (1 liter) and water (1 liter). The organic phase is dried (Na2SO4), filtered, and evaporated. The residue is washed with. hexanes (2*500 mL) to remove excess 2-(4-chlorophenyl)ethyl bromide, then dissolved in dichloromethane (250 mL), adsorbed onto silica gel (100 g), and chromatographed over silica gel (1000 g) using a gradient of ethyl acetate (30%?50%) in hexanes. Fractions containing product are collected and evaporated to dryness to afford the desired intermediate as a yellow foam. Typical yield: 40-70% for Steps C and D combined. 1H-NMR (DMSO-d6): delta8.06 (s, 1H, H-8), 7.25 (s, 4H, Ar), 6.10 (d, 1H, H-1', J=4.8 Hz), 5.90 (dd, 1H, H-2', J=5.3, 5.0 Hz), 5.62 (dd, 1H, H-3', J=5.3, 5.2 Hz), 4.63-4.56 (m, 2H, OCH2-C), 4.43-4.37 (m, 2H, H-4' & H-5'alpha), 4.29 (dd, 1H, H-5'beta, J=12.0, 4.1 Hz), 3.11 (t, 2H, O-C-CH2-, J=6.9 Hz), 2.10 (s, 3H, COCH3), 2.06 (s, 3H, COCH3), 2.05 (s, 3H, COCH3). ; Step D: Preparation of 6-chloro-2-[2-(4-chlorophenyl)ethoxy]-9-(2,3,5-tri-O-acetyl-[beta]-D-ribofuranosyl)purineEMI8.0[0062] To a mixture of 6-chloro-2-hydroxy-9-(2,3,5-tri-O-acetyl-[beta]-D-ribofuranosyl)purine (Example 2, Step C) and 2-(4-chlorophenyl)ethyl bromide (300.1 g, 1.36 mol) in dimethylformamide (7,280 mL), cesium carbonate (665 g, 2.04 mol) was added. The reaction was allowed to stir under inert atmosphere for 32 hours. The reaction was concentrated under reduced pressure and partitioned between dichloromethane and water. The organic layer was dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography eluting with ethyl acetate/heptanes to yield a yellow solid of 6-chloro-2-[2-(4-chlorophenyl)ethoxy]-9-(2,3,5-tri-O-acetyl-[beta]-D-ribofuranosyl)purine Typical Yield: 64% According to the analysis of related databases, 6529-53-9, the application of this compound in the production field has become more and more popular. Reference:
Patent; Moorman, Allan R.; US2003/199686; (2003); A1;,
Chloride – Wikipedia,
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Synthetic Route of 116369-24-5,Some common heterocyclic compound, 116369-24-5, name is 4-Bromo-5-chloro-2-fluoroaniline, molecular formula is C6H4BrClFN, 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 4-bromo-5-chloro-2-fluoroaniline (0.5 g, 2.24 mmol) to 1,4-dioxane (8.0 mL) and water (4.0 mL), and then add 1-isopropyl-5 in this order. -(4,4,5,5-tetramethyl-1,3,2-dioxorane-2-yl) pyridine-2 (1H) -one (0.65 g, 2.46 mmol),Potassium carbonate (0.94g, 6.72mmol) and Pd (dppf) Cl2 (0.1g, 0.12mmol),After replacing with nitrogen three times, the reaction was carried out at 80 C for 10 hours.After the reaction is completed, cool to room temperature, pour the reaction solution into water, extract with ethyl acetate, combine the organic phases, dry, filter, and concentrate. The residue is purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether). = 3/1),The title compound (0.4 g, yield: 64%) was obtained in this step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-5-chloro-2-fluoroaniline, its application will become more common.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Jinming; Cai Jiaqiang; He Ting; Wang Lichun; Wang Jingyi; (27 pag.)CN110240593; (2019); A;,
Chloride – Wikipedia,
Chlorides – 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. 823-57-4, name is 2-Bromo-5-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H5BrClN

2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxide (50 wtpercentsolution in ethyl acetate, 8.1 mL, 13.6 mmol) was added slowly to a stirred solution of2-15 bromo-5-chloroaniline (1.5 g, 7.27 mmol), thiane-4-carboxylic acid (1.0 g, 6.84 mmol)and pyridine (2.7 mL, 33.4 mmol) in ethyl acetate (14 mL) at ooc under nitrogen. Thereaction mixture was allowed to warm slowly to 20°C and stirred for 64 h. The resultantsuspension was diluted with ethyl acetate (20 mL) and quenched with water (30 mL).The solids were collected by filtration, washing sequentially with ethyl acetate (2 x 2020 mL), water (20 mL) and diethyl ether (2 x 20 mL). The solids were dried at 50°C invacuo for 16 h, to afford the title compound (2.08 g, 86percent) as a pink powder. DH (500MHz, DMSO-d6) 9.51 (br s, 1H), 7.71-7.65 (m, 2H), 7.21 (dd, J8.6, 2.6 Hz, 1H), 2.71-2.62 (m, 4H), 2.57 (tt, J 11.5, 3.1 Hz, 1H), 2.19-2.08 (m, 2H), 1.78-1.63 (m, 2H). HPLCMS(method 5): MH+ m/z 334, RT 1.90 minutes.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); A1;,
Chloride – Wikipedia,
Chlorides – 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 933190-51-3

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (2 g, 8.6 mmol) and 5,6-dimethoxypyridin-2-amine (1.39 g, 9.03 mmol) in DMF (72 ml) was cooled to 0 C. To the mixture was added sodium hydride (1.1 g, 27.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 10 min then warmed to room temperature. After 15 h the reaction was quenched with saturated sodium bicarbonate solution, and then diluted with water and EtOAc. An insoluble solid was filtered off. The filtrate was separated and the aqueous phase was washed with EtOAc. The combined organic extracts were concentrated in vacuo and the residue obtained was crystallized from methanol to give 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (2.4 g, 7.85 mmol, 91.2%) as light brown needles. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 8.26 (br. s., 1H) 7.95 (s, 1H) 7.81 (s, 1H) 7.55 (s, 1H) 7.15 (d, J=7.93 Hz, 1H) 6.58 (d, J=8.31 Hz, 1H) 4.12 (s, 3H) 3.89 (s, 3H); LC/MS: 305.9 [MH]+.

According to the analysis of related databases, 933190-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1, Recommanded Product: 3-Bromo-4-fluorochlorobenzene

To a solution of 2-bromo-4-chloro-l-fluorobenzene (2093 mg, 9.99 mmol) and 4- (trifluoromethyl)-l//-pyrazole (800 mg, 5.88 mmol) in iVW-dimethylacetamide (10 mL) was added Cs2C03(3831 mg, 11.76 mmol). The mixture was heated to 80C for 12 h. LCMS showed the reaction was completed. The mixture was diluted with water (40 mL), extracted with EtOAc (60 mL x 3). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography on silica (100:1-5:1 petroleum ether: EtOAc) to give the title compound. LCMS (ES, m/z): 325.0, 326.9 [M+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-Bromo-4-fluorochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; DEBENHAM, John, S.; ZHU, Cheng; (64 pag.)WO2020/86416; (2020); A1;,
Chloride – Wikipedia,
Chlorides – 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. 14862-52-3, name is 3,5-Dibromochlorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C6H3Br2Cl

To a solution of 1,3-dibromo-5-chlorobenzene (500 mg, 1.85 mmol) in THF (1 ml) was added cyclopropylmagnesium bromide (3698 mul, 0.5M solution in THF, 1.85 mmol) in a sealed tube and the reaction mixture was degassed with argon for 5 min before tetrakis(triphenylphosphine)palladium (0) (107 mg, 0.09 mmol) was added. The resulting solution was heated to 70 C. overnight, cooled to RT and then quenched with sat. NH4Cl solution and extracted with pentane. The organic phases were combined, washed with water and brine, dried over MgSO4 and filtered through a short pad of silica gel to give the desired product (272 mg, 64%) which did not require further purification. 1H NMR (CDCl3, 300 MHz): 7.28 (aptt, J=2.0 Hz, 1H), 7.08 (aptt, J=1.5 Hz, 1H), 6.97 (aptt, J=1.5 Hz, 1H), 1.83 (m, 1H), 1.04-0.97 (m, 2H), 0.72-0.67 (m, 2H).

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; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185058; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 19230-27-4, A common heterocyclic compound, 19230-27-4, name is 1,3-Dibromo-2-chlorobenzene, molecular formula is C6H3Br2Cl, 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.

To a mixture of 1,3-dibromo-2-chlorobenzene (1.47 g, 5.45 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (800 mg, 3.64 mmol), Pd(dppf)C12CH2C12 (297 mg, 0.36mmol) and potassium carbonate (1.005 g, 7.27 mmol) under N2 was added a mixture of solvents (12 mL and 3 mL water) and heated to 85 C for 2h. After cooling to room temperature, the reaction was dilutedwith CH2C12 and water. The organic layer was separated, dried with Na2504 and concentrated. The residue was purified by silica gel chromatography (eluting with 5% to 40% EtOAc-Hex) to give 3?- bromo-2?-chloro- [1,1 ?-biphenyll -4-ol.

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; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.

[0 144j To a solution of 5 -(aminomethyl)-N-((2-methylthiazol-5 -yl)methyl)pyrazine-2- carboxamide (0.070 g, 0.26 mmol) and 3,5-difluorobenzenesulfonyl chloride (0.056 g, 0.26 mmol) in dichioromethane (2 mL) was added triethylamine (0.1 mL, 0.53 mmol) at 0 C and resulting solution was stirred at room temperature for 1 h. The reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (15 mL x 3). The organic layer was washed with saturated sodium bicarbonate solution (10 mL x 2), brine (20 mL), dried over sodium sulfate and concentrated under vacuum to get the crude material which was purified by preparative HPLC (analytical conditions: column: Xbridge C18 (19 mm X 250 mm X 5 jim), mobile phase (A): 5 mM ammonium acetate in water, mobile phase (B): HPLC grade acetonitrile. Elution gradient: 0-20 mm, 5-95% B in A) to afford the title compound 5-(((3,5- difluorophenyl)sulfonamido)methyl)-N-((2-methylthiazol-5 -yl)methyl)pyrazine-2-carboxamide (0.013 g, 12% yield) as an off-white solid. Calculated M+H: 440.06; Found M+H: 440.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Difluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 220227-21-4, 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 220227-21-4 as follows.

Into a 100-mL round-bottom flask, were placed 3-(chloromethyl)-1 ,2,4-thiadiazol-5-amine (1 .00 g, 6.68 mmol, 1 .00 equiv), N,N-dimethylformamide (30 m L), sodium hydride (242 mg, 10.08 mmol, 1 .50 equiv), 2,4,5-trifluorobenzene-1 -sulfonyl chloride (1 .85 g, 8.02 mmol, 1 .00 equiv). The resulting solution was stirred for 1 .5 h at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with ethyl acetate and the organic layers combined. The resulting mixture was washed with brine, dried and concentrated under vacumm. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :6). This resulted in 700 mg (30%) of N-[3- (chloromethyl)-l ,2, 4-thiadiazol-5-yl]-2, 4, 5-trifluorobenzene-1 -sulfonamide as a yellow solid.

According to the analysis of related databases, 220227-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZALICUS PHARMACEUTICALS, LTD.; SHORT, Glenn, F., III; ROMERO, Donna, L.; LEE, Margaret, S.; WO2015/130957; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics