Tag: M.W=100-200

Reference of 6940-78-9, A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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.

Compound (1) 7-hydroxy-2-quinolone (10.0 g, 62 mmol), 120 ml of ethanol and potassium carbonate (19.0 g, 138 mmol) were added in a 500ml reaction bottle .Compound (II) 1-bromo-4-chlorobutane (12.0 g, 70 mmol) was added with stirring, the temperature was raised to reflux and stirred for 2 hours. 100 ml of water and the compound (IV) 1-(benzo[b]thiophen-4-yl) piperazine hydrochloride (15.0 g, 59 mmol) were added, and the mixture was stirred under reflux for 9 hours. Part of the solvent was distilled off, cooled to 50 C, 40 ml of ethyl acetate was added and stirred for 0.5 hour, then continued to cooled down below 20 C, after filtration under reduced pressure, the filter cake was washed three times with 20 ml of ethanol, and then dried in a blast oven at 70 C for 3 hours. Brexpiprazole (Compound V) 14.5 g was obtained in a molar yield of 54%, which was substantially the same as the molar yield of 55% of the method described in Scheme 2.

The synthetic route of 6940-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Xin Bosi Bio-pharmaceutical Co., Ltd.; Du Huanda; Ding Jiansheng; Ye Xinjie; Wang Zhenyu; Chen Yu; Wang Wanqing; Han Lu; Liu Yanhua; (8 pag.)CN105061414; (2019); B;,
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102-49-8, name is 3,4-Dichlorobenzylamine, 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. Formula: C7H7Cl2N

Example 316 ethyl 4-[({[2-({[(3,4-dichlorophenyl)methyl]amino}carbonyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl]methyl}oxy)methyl]benzoate A suspension of ethyl 5-{[({4-[(ethyloxy)carbonyl]phenyl}methyl)oxy]methyl}-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (0.400 g, 0.961 mmol) obtained in Reference Example 158 and 1-(3,4-dichlorophenyl)methanamine (0.287 g, 1.63 mmol) in ethanol (16 mL) was stirred with heating at 80° C. for 15 hrs. The mixture was allowed to cool to room temperature and the precipitated solid was collected by filtration and washed with ethanol to give the title compound as a white powder (475 mg, 91percent). melting point: 253-254° C.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
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6781-98-2, name is 2-Chloro-1,3-dimethylbenzene, 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. category: chlorides-buliding-blocks

General procedure: Under N2 atmosphere, KOtBu (1.3 equiv), toluene (1.0 mL), amines 5 (0.84 mmol), aryl chlorides 4 (0.7 mmol) and finally a solution of complex 3a (20?100muL, 0.01?0.05 molpercent, prepared from 0.014 mmol 3a in 4.0mL toluene) were successively added into a Schlenk reaction tube. The mixture was stirred vigorously at 110 °C for 24h. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding products.

The synthetic route of 6781-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Feng; Hu, Yuan-Yuan; Li, Di; Zhou, Quan; Lu, Jian-Mei; Tetrahedron; vol. 74; 39; (2018); p. 5683 – 5690;,
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Related Products of 1939-99-7, A common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl chloride, molecular formula is C7H7ClO2S, 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.

Ethyl piperidine-2-carboxylate (100mg, 0.63 mmol) was dissolved in 5mL of anhydrous DMF, and triethylamine (191mg, 1.89 mmol) was added drop wise followed by phenylmethanesulfonyl chloride (119.7mg, 0.63 mmol). The reaction was stirred for 6h at RT and subsequently the solvent was removed in vacuo. The crude mixture was purified using column chromatography (hexane : EtOAc 8:2) to yield Ethyl 1-(benzylsulfonyl)piperidine-2-carboxylate_(170mg, 0.55 mmol, 86%). TLC (hexane: EtOAc 8:2): Rf = 0.20. HPLC (gradient A) retention time= 23.4-23.8 min 1HNMR (300 MHz, CDCl3) delta= 1.14-1.25 (m, 1H), 1.28 (t, 3H, J= 7.2 Hz), 1.34-1.49 (m, 1H), 1.54-1.68 (m, 3H), 2.14 (d, 1H, J= 13.5 Hz), 3.14 (dt, 1H, J= 3.3, 12.6 Hz), 3.44 (d, 1H, J= 12.6 Hz), 4.18-4.24 (m, 2H), 4.26 (s, 2H), 4.54 (d, 1H, J= 4.8 Hz), 7.31-7.38 (m, 3H), 7.43-7.48 (m, 2H). 13C NMR (75 MHz, CDCl3) delta= 14.22, 20.31, 25.04, 27.78, 43.39, 55.95, 58.71, 61.36, 128.40, 128.48, 129.35, 130.96, 171.38. MS (ESI) m/z: found Rt 14.28 min. (Method LCMS), 312.12 [M + H]+, 334.22 [M + Na]+. calculated 312.12 [M + H]+, 334.11 [M + Na]+.

The synthetic route of 1939-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Gopalakrishnan, Ranganath; Hausch, Felix; EP2610245; (2013); A1;,
Chloride – Wikipedia,
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Reference of 118-69-4, 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 118-69-4 as follows.

Example 1Preparation of DCDNTTo a 1 L 3-neck round bottom flask equipped with external ice cooling, mechanical stirrer, addition funnel, N2 inlet, and thermometer was added 174 g (2.76 mol) fuming nitric acid (d=1.54), followed by 350 g sulfuric acid and 659 g 30% oleum (2.0 molar equiv SO3) maintaining a temperature between 5 and 20 C. Subsequently, 199 g (1.23 mol) 1,3-dichlorotoluene (99% purity, Aldrich Chemical Company, Milwaukee, Wis., USA) was added over a time period of 3 h while maintaining a temperature between 0 C.-10 C. The ice bath was removed, and the reaction mixture was allowed to warm up to room temperature. It was then heated to 100 C. for about 2 h. To analyze the reaction mixture, a small sample of crude product was taken from the reaction vessel and poured into ice water. The crude product was extracted with methylene chloride. Analysis by GC indicated a reaction selectivity to 3,5-dinitro-2,6-dichlorotoluene of >97%. Subsequently, the reaction mixture was allowed to cool to room temperature over 2 h and then cooled to 5 C. over 30 min, after which it was filtered through a glass fritted funnel and washed with a little sulfuric acid followed by 200 mL H20. The wet cake contained about 20% water. After drying, 291 g of >99.5% pure DCDNT product (by 1H-NMR) was isolated (93.5% net yield).

According to the analysis of related databases, 118-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; US2010/160685; (2010); 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. 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene, A new synthetic method of this compound is introduced below., Formula: C7H6ClFO

1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF was cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane were added. After one hour at -70 3.93 ml DMF in 7 ml THF were added at -70 C. and the mixture is stirred another hour at -70 C. 15 ml of a 1 M aqueous hydrochloric acid were added and the reaction was warmed to ambient temperature over 18 hours. The reaction mixture was partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether, the combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

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; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; ASTRAZENECA AB; US2010/16338; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2613-34-5, The chemical industry reduces the impact on the environment during synthesis 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, I believe this compound will play a more active role in future production and life.

3-Chloro-2,4-difluoro-(trifluoroacetamido)benzene. To a solution of 10.5 g (64.3 mmol) of 3-chloro-2,4-difluoroaniline in 25 mL of dioxane kept in an ice-bath was added dropwise 10 mL (14.8 g, 70.4 mmol) of trifluoroacetic anhydride. The solution was stirred at room temperature for 20 h. It was then added to 150 mL of ice-water and the mixture was stirred for 1 h. It was filtered, washed with water, and dried to leave an almost colorless solid 16.1 g (96%); mp 73-74 C.; 1 H NMR (CDCl3), 7.068 (m, 1), 7.976 (mb, 1), 8.146 (m, 1).

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

Reference:
Patent; State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon, Eugene Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5631373; (1997); A;,
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Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 367-22-6, name is 4-Chloro-3-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 367-22-6, category: chlorides-buliding-blocks

Step B: 4-Chloro-5-fluoro-2-iodo-phenylamine Iodine chloride (20.6 ml, 1M solution in DCM, 20.6 mmol) was added dropwise to a solution of 4-chloro-3-fluoroaniline (2 g, 13.7 mmol) in methanol (35 ml) at 0 C. and the reaction mixture was stirred for 1 h at room temperature. Volatiles were removed under reduced pressure, water was added and the mixture was extracted with dichloromethane. The combined organic layers were washed with water, dried with Na2SO4 and evaporated. The remaining residue was purified by chromatography with three consecutive columns (silica gel, heptane/EtOAc 98:2-93:7 and twice heptane/EtOAc 98:2-95:5) to obtain the title compound (2.51 g, 67%) as dark red solid. MS (ESI): 272.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Ceccarelli, Simona M.; Conte, Aurelia; Kuehne, Holger; Kuhn, Bernd; Neidhart, Werner; Obst Sander, Ulrike; Rudolph, Markus; US2013/116234; (2013); A1;,
Chloride – Wikipedia,
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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. 1939-99-7, name is Phenylmethanesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., name: Phenylmethanesulfonyl chloride

Step 1 : N-re^butyl-1 -phenylmethanesulfonamide To a solution of teri-butylamine (2 g, 27.3 mmol) in dichloromethane (90 mL) was added N,N-diisopropylethylamine (5.7 mL, 32.8 mmol), followed by phenylmethanesulfonyl chloride (6.25 g, 32.8 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was then diluted with dichloromethane, washed with water and brine, dried with MgS04, and purified by silica gel column chromatography (0-50% EtOAc in heptane) to give N-teri-butyl-l-phenyl- methanesulfonamide (4.81 g, 77% yield). 1 H NMR (400 MHz, CDC13) delta 7.51 – 7.44 (m, 2H), 7.41 (dd, J= 4.9, 2.0 Hz, 3H), 4.49 (s, 2H), 4.27 (s, 1H), 1.68 (s, 6H); LCMS (m/z) ES+ 228 [M+l]+.

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FAUBER, Benjamin; RENE, Olivier; WO2013/92941; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33406-96-1, A common heterocyclic compound, 33406-96-1, name is 1-Chloro-4-fluoro-2-methylbenzene, molecular formula is C7H6ClF, 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: A mixture of aryl chloride (0.125 mmol), aryl boronic acid (0.15 mmol) and K4PO3 (0.25 mmol), catalyst (0.000125 mmol) in H2O (0.1 mL), isopropanol (0.1 mL) was stirred in a test tube at 45 C. After the reaction was completed, cooled to room temperature and the mixture was extracted with CH2Cl2 and dried over Na2SO4. The solvent was removed under vacuum. The product was purified by flash chromatography on a silica gel column. The characterization of all coupling products see Supporting Information.

The synthetic route of 33406-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fangwai; Li, Yanji; Liu, Guiyan; Lu, Qingwen; Ni, Chang; Zeng, Yongfei; Zhang, Rong; Zhang, Xue; Zhang, Yingying; Zhao, Yuxuan; Tetrahedron Letters; (2019);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics