Tag: M.W=200-300

Synthetic Route of 1435-50-3, 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 1435-50-3 as follows.

Step 4) tert-butyl 4-(4-(3-((2.5-dichlorophenyl ethvnyl -lH-pyrrolor2.3-b1pyridin-5-yl -lH- pyrazol- 1 -yPpiperidine- 1 -carboxylate To a suspension of tert-butyl 4-(4-(3-ethynyl-lH-pyrrolo[2,3-b]pyridin-5-yl)-lH-pyrazol-l- yl)piperidine-l -carboxylate (0.20 g, 0.51 mmol) in DMF (15 mL) was added Pd(PPh3)2Cl2 (36 mg, 0.051 mmol), Cul (10 mg, 0.051 mmol) and l,4-dichloro-2-bromobenzene (0.12 g, 0.51 mmol). The mixture was degassed and charged with nitrogen for three times, then Et3 (1.4 mL, 10.2 mmol) was added. The mixture was stirred at 75 C for 2 hours. After the removal of the solvent, the residue was diluted with DCM (100 mL), and then washed with brine (100 mL x 2). The separated organic phase was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 1/2) to give the title compound as a yellow solid (0.17 g, 62%). MS (ESI, pos. ion) m/z: 536.1 (M+l); FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, CDC13): delta 1.42 (s, 9H), 1.86 (m, 2H), 2.04 (m, 2H), 2.95 (m, 2H), 4.05 (m, 2H), 4.39 (m, 1H), 7.47 (dd, J=8.7 Hz, 2.6 Hz, 1H), 7.61 (d, J=8.7 Hz, 1H), 7.83 (d, J=2.5 Hz, 1H), 7.97 (d, J=2.6 Hz, 1H), 8.01 (s, 1H), 8.21 (d, J=1.9 Hz, 1H), 8.39 (s, 1H), 8.62 (s, 1H), 12.27 (s, 1H).

According to the analysis of related databases, 1435-50-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Xiaobo; ZHOU, Shiqing; WO2014/89280; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 63624-28-2, The chemical industry reduces the impact on the environment during synthesis 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

To a solution of tert-butyl 3-(4-aminonaphthalen-1-yl)benzoate (70 mg, 0.22 mmol) in dichloromethane (2 mL) were added pyridine (35 muL, 0.4 mmol) and 2,4-dimethoxy-benzenesulfonyl chloride (100 mg, 0.4 mmol). The reaction mixture was stirred at room temperature for 30 h. Afterwards the reaction mixture was diluted with dichloromethane (5 mL) and washed with hydrogen chloride (1 M aqueous solution), dried over magnesium sulfate, filtered and then concentrated in vacuo. The resulting residue was dissolved in dichloromethane (3 mL). Trifluoroacetate (0.3 mL, 4 mmol) was added and the reaction mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo and the resulting residue was purified by high performance liquid chromatography (RP silica gel, cetonitrile/water/trifluoroacetic acid). Lyophilization of the product fractions provided 48 mg, 47% of the title compound as a white powder.

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, 2,4-Dimethoxybenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; The designation of the inventor has not yet been filed; (58 pag.)EP2998294; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

201849-21-0, name is 4-Bromo-2-chloro-1-isopropoxybenzene, 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. Safety of 4-Bromo-2-chloro-1-isopropoxybenzene

To a suspension of 4-bromo-2-chloro-1-[(1-methylethyl)oxy]benzene (D10) (10 g), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi-1,3,2-dioxaborolane (15.26 g) and potassium acetate (15.73 g) in N,N-dimethylformamide (DMF) (150 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (1.964 g). The reaction mixture was stirred at 80 C. overnight. After cooling the reaction, the reaction mixture was concentrated in vacuo, the residue was diluted with ethyl acetate and filtered through celite, the filtrate was washed with water and brine, the organic phase was dried over anhydrous Na2SO4. After removing the solvent, the residue was purified by column chromatography to give 2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (D11) (11.8 g). MS (ES): C15H22BClO3 requires 296; found 297.1 (M+H+).

The synthetic route of 201849-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; Lin, Xichen; Ren, Feng; Zhang, Haibo; US2013/12491; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.

Alcohol 15* (136 mg, 0.19 mmol) was dissolved in CH2CI2(2 mL). Levulinic acid (0.1 mL, 0.96 mmol), 4-dimethylaminopyridine (140 mg, 1 .15 mmol) and di-/sopropylcarbodiimide (0.15 mL, 0.96 mmol) were added. The reaction mixture was stirred at r.t. overnight. The mixture was diluted with CH2CI2, washed with brine and then concentrated in vacuo. The crude product was purified by chromatography column on silica gel (Hexanes/EtOAc = 1 :1 ) to afford the levulinate ester (150 mg, 97%). The levulinate ester (161 mg, 0.199 mmol) was dissolved in acetone and water (6.25 mL, v/v = 4/1 ) at 0 C. TCCA (46 mg, 0.199 mmol) was added. The reaction mixture was allowed to warm to r.t. overnight. The reaction mixture was diluted with ethyl acetate, washed with sat NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (Hexanes/EtOAc = 1/2) to give the hemiacetal (121 mg, 79%). To a solution of hemiacetal (121 mg, 0.158 mmol) in acetone (3 mL) was added K2CO3(66 mg, 0.48 mmol) and PhN=C(CI)CF3(98 mg, 0.48 mmol). The mixture was stirred overnight at r.t.. The solution was filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (Hexanes/EtOAc = 2.2/1 to 1/1 ) to give the imidate 24* (139 mg, 94%). [a]D25= 59.57 (c = 0.25, CHCIs);1H NMR (400 MHz, CDCI3) delta 7.31 -7.25 (m, 16H), 7.19 (m, 1 H), 7.09 (m, 1 H), 6.73 (m, 3 H), 5.42 (brs, 1 H), 5.31 (dd, J = 2.0, 10.8 Hz, 1 H), 4.97 (br, 1 H), 4.86 (d, J = 10.8 Hz, 1 H), 4.74-4.56 (m, 6 H), 4.37 (d, J = 1 1 .2 Hz, 1 H), 4.01 (dd, J = 2.8, 10.4 Hz, 1 H), 3.79 (s, 3 H), 3.77 (m, 1 H), 3.68 (m, 1 H), 3.36 (t, J = 9.6 Hz, 1 H), 2.89-2.69 (m, 3 H), 2.52 (m, 1 H), 2.18 (s, 3 H), 2.1 1 (s, 3 H), 1 .29 (d, J = 6.4 Hz, 3 H);13C NMR (101 MHz, CDCI3) delta 206.31 , 172.54, 170.44, 167.16, 143.40,138.75, 138.08, 137.33, 128.88, 128.64, 128.53, 128.38, 128.23, 128.20, 127.89,127.76, 127.67, 127.61 , 124.44, 1 19.45, 100.57, 79.70, 77.76, 77.31 , 75.19, 73.1 1 , 72.07, 72.01 , 71 .75, 71 .18, 68.94, 68.86, 52.79, 37.97, 29.81 , 27.86, 21 .27, 18.08; HRMS (ESI): calcd for C49H52F3NOi4Na [M + Na]+: 958.3238, found: 958.3303.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, its application will become more common.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; SEEBERGER, Peter; PEREIRA, Claney Lebev; XIAO, Guozhi; KHAN, Naeem; ANISH, Chakkumkal; (120 pag.)WO2016/156338; (2016); A1;,
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. 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 39226-96-5

Example 8 /V-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4- imidazolidinecarboxamide (E8) (e.g. in a form obtainable or prepared from (4S)-2- oxo-S-^phenylmethy^oxyJcarbonylJ^-imidazolidinecarboxylic acid); Crude 3-methyl-2-oxo-4-imidazolidinecarboxylic acid (-0.63 mmol, prepared as described below) was dissolved in dimethylformamide (3 ml) and treated with 1- hydroxybenzotriazole (0.094 g, 0.69 mmol), N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (0.132 g, 0.69 mmol), [(2-chloro-3- trifluoromethylphenyl)methyl]amine (0.145 g, 0.69 mmol) and N-ethylmorpholine (0.169 ml, 1.32 mmol). The mixture was stirred at 22C for 20 hours then reduced in vacuo to give a residue which was purified by mass-directed automated HPLC to give lambda/-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-4- imidazolidinecarboxamide as a white solid (0.105 g). LC/MS [M+H]+ = 336, retention time = 2.18 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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. name: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

Comparative Example 1 e -Bromo-6-chloro-3-iodoimidazo[1 ,2-b]pyridazine A mixture comprising 100 g (430 mmoi) 8-bromo-6-chloroimidazo[1 ,2-b]pyridazine which was prepared according to a procedure described in US2007/78136 (WO2007/38314) , 145 g N-iodosuccinimide, 5 percent per weight cone, hydrochloric acid and 1 L trichloromethane was heated at reflux for 6 hours. 20 g N- iodosuccinimide were added and heating was continued for additional 3 hours. The precipitate was removed and the filtrate was washed with 1 N sodium hydroxide solution, brine and dried over sodium sulfate. After filtration and removal of solvent diisopropyl ether was added and the residue was stirred at 23 C overnight. The precipitate was filtered off and dried to give 66.6 g (43%) of the title compound

The synthetic route of 8-Bromo-6-chloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; WENGNER, Antje Margret; NEUHAUS, Roland; SIEMEISTER, Gerhard; WO2013/135612; (2013); 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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6BrCl

General procedure: Nitrogen was purged through a stirred solution of 4-bromo-1-chloro-2-methylbenzene (258muL, 1.95mmol) in 1,4-dioxane (5mL) for 30min rac-BINAP (363mg, 1.95mmol), caesium carbonate (1.27g, 3.89mmol), 1-Boc-piperazine (363mg, 1.95mmol) and Pd(OAc)2 (87mg, 0.039mumol) and stirred at reflux for 14h under N2. The reaction was filtered through celite and concentrated in vacuo. The residue was dissolved in EtOAc (20mL), filtered through celite and washed with additional EtOAc (50mL). The organic layer was washed with water (2¡Á20mL) and brine (2¡Á20mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain the protected intermediate as a solid (413mg, 68%). MS, m/z=255 (100) [M-tBu]. The intermediate was dissolved in a 1:3 mixture of TFA/DCM (4mL) and stirred at 20C for 1h. The solvent was evaporated in vacuo and the crude residue dissolved in EtOAc (10mL) which was successively washed with a 10% solution of NaHCO3 (10mL), water (10mL) and brine (10mL). The organic layer dried with Na2SO4 and concentrated in vacuo to obtain 92 as a solid (211mg, 76%).

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 54932-72-8.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13918-92-8, A common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below., SDS of cas: 933190-51-3

A solution of 6-(trifluoromethyl)pyridin-2-amine (0.668 g, 4.12 mmol) in DMF (5 mL) was added NaH (0.10 g, 4.18 mmol) and stirred for 0.5 h. To the mixture was added 8-bromo-6- chloroimidazo[l,2-b]pyridazine (0.38 g, 1.65 mmol) under N2. The mixture was stirred at room temperature for 16 h then 100 mL of water was added and the precipitate collected by filtration and washed with water to give 6-chloro-N-(6-(trifluoromethyl)pyridin-2-yl)imidazo[l,2- b]pyridazin-8-amine (0.513 g, 99 %) as a light brown solid. LC-MS: [M+H]+, 314.1 , tR = 1.738 min.

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; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 766545-20-4, 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 766545-20-4 as follows.

To a solution of 2-chloro-5,6,7,8-tetrahydro-l,6-naphthyridine hydrochloride (available from Activate Scientific) (3.0 g, 15 mmol) in DCM (50 mL) was added NEt3 (4.44 g, 6.1 mL, 44 mmol). After 15 min, methylchloroformate (2.1 g, 1.7 mL, 22 mL) was added and the resulting mixture stirred at RT for 16 h. The reaction was diluted with DCM, washed with saturated NaHCO3 (aq.), then brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by FCC (SiO2, eluting with 2:1 heptane / EtOAc) to give the title compound (3.17 g, 96%) as white solid.LCMS data: Calculated MH+ (227); Found 100% (MH+) m/z 227, Rt = 1.11 (2 min method). 1H NMR (500 MHz, CHLOROFORM-J) delta ppm 7.38 (1 H, br. s.), 7.18 (1 H, d, J=8.1 Hz), 4.62 (2 H, br. s.), 3.78 – 3.83 (2 H, m), 3.72 (3 H, s), 3.00 (2 H, t, J=5.3 Hz).

According to the analysis of related databases, 766545-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/121812; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics