Month: December 2020

Some common heterocyclic compound, 166176-45-0, name is 6-Chloroimidazo[1,2-b]pyridazin-3-amine, molecular formula is C6H5ClN4, 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. Recommanded Product: 6-Chloroimidazo[1,2-b]pyridazin-3-amine

To a solution 6-chloroimidazo[1,2-b]pyridazin-3-amine and triethylamine (0.8 ml, 6.0 mmol)in DCM (25 ml) was added acetyl chloride dropwise and stirred at rt for overnight. The mixture was30 concentrated and purified by ISCO column chromatography (10% MeOH/DCM) to give not very pure N-(6-chloroimidazo[1,2-b]pyridazin-3-yl)acetamide (500 mg, 95% yield). 60 mg of non-pure materialwas further purified by Prep HPLC (neutral) to give pure N-(6-chloroimidazo[1,2-b]pyridazin-3-yl)acetamide. 1H NMR (400 MHz, METHANOL-d4) 8 ppm 8.01 (d, J=9.35 Hz, 1 H), 7.94 (s, 1 H), 7.26(d, J=9.35 Hz, 1 H), 2.29 (s, 3 H); LRMS (ESI) mje 210.9 [(M +H)+, calcd for CsHsCIN40 211.6].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 166176-45-0, its application will become more common.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; CARSON, Kenneth Gordon; CIANCHETTA, Giovanni; GREEN, Michael Alan; KUMI, Godwin; LIANG, Zhi; LIU, Ying Jade; MAIN, Alan; ZHANG, Yulian; ZIPP, Glenn Gregory; WO2013/134219; (2013); A1;,
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Electric Literature of 1124-05-6, A common heterocyclic compound, 1124-05-6, name is 2,5-Dichloro-p-xylene, molecular formula is C8H8Cl2, 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 acetic acid (300 g, 5.00 mol, 25.0 equiv), acetic anhydride (600 g, 5.88 mol, 29.4 equiv) and sulfuric acid (90.0 g, 899 mmol, 4.50 equiv, 98%) at 0-10 C was added 1,4- dichloro-2,5-dimethylbenzene (35.0 g. 200 mmol, 1.00 equiv), and followed by addition of chromium trioxide (60.0 g, 600 mmol, 3.00 equiv) in several batches over 2 h. The resulting solution was stirred for 4 h at room temperature, and then quenched by the addition of 2000 mL of crushed ice. The resulting solution was extracted with 3×1000 mL of ethyl acetate and the organic layers were combined and concentrated under reduced pressure to give a solid. The solid was added to a mixture of ethanol (300 mL), water (300 mL), and sulfuric acid (30 mL), and the mixture was heated to reflux for 3 h and then cooled. The solids were collected by filtration. The solid was purified by column with ethyl acetate/petroleum ether (1 :30) to give 12 g (30%) of 2,5- dichloroterephthalaldehyde as a white solid.

The synthetic route of 1124-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
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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;,
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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. 108-37-2, name is 1-Bromo-3-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-3-chlorobenzene

General procedure: In a round-bottom flask equipped with a magnetic stirring bar to a mixture of K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 ml) were added 0.1 mol% of palladacycle complex (A) and equipped with a condenser for refluxing. The above mixture was heated at 130 C in an oil bath. The reaction’s progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completion of the reaction the mixturewas diluted with n-hexane and water. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from ethanol and water. The products were characterized by comparing their m.p., IR, 1H, 13C NMR spectra with those found in the literature [41-43].

According to the analysis of related databases, 108-37-2, the application of this compound in the production field has become more and more popular.

Reference:
Short Survey; Hajipour, Abdol R.; Rafiee, Fatemeh; Journal of Organometallic Chemistry; vol. 696; 13; (2011); p. 2669 – 2675;,
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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. 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;,
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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. 6781-98-2, name is 2-Chloro-1,3-dimethylbenzene, A new synthetic method of this compound is introduced below., SDS of cas: 6781-98-2

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 mol%, 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 2106-04-9, These common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, 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.

A suspension of compound 5 (1.70 g, 6.75 mmol) and 3-chloro-2-fluoroaniline (982 mg, 6.75 mmol) in i-PrOH (50 mL) was heated to reflux for 3 h. The solvent was removed under vacuum, and the residual was recrystallized in CH3CN to afford 6 (2.51 g, 93%) as a pale brown solid, mp 209-210 C. 1H NMR (DMSO-d6): d 9.82 (br s, 1H), 8.48 (s, 1H), 8.23 (s, 1H), 7.53-7.47 (m, 2H), 7.37 (s, 1H), 7.28 (t, J = 8.0 Hz, 1H), 3.96 (s, 3H), 2.37 (s, 3H). LC-MS (ESI, m/z): calcd for C17H14ClFN3O3 ([M+H]+) 362.0, found 362.0.

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Min; Gao, Mingzhang; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 24; 18; (2014); p. 4455 – 4459;,
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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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H5ClFN

Step 7. Preparation of compound (I). 2-[4-(5-cyano-4-{ [(dimethylamino)methylene] amino } -2-methoxyphenoxy)piperidin- 1 -yl] -JV-methylacetamide (compound (II),; 7.00 g, 17.71 mmoles), was suspended in methoxybenzene (35.8 g). Acetic acid (16.6 g) was charged and to the resulting solution was added 3-chloro-2-fluoroaniline (2.71 g, 18.07 mmoles). The reaction mixture was heated at 90 0C for 20 hours then cooled to 200C. Water (37.04 g) was charged to the reaction mixture, and the organic layer discarded. To the resulting aqueous mixture was charged isopropanol (39.00 g), followed by aqueous ammonia (20.79 g, 25%). The reaction mixture was heated to 30 0C and seeded with compound (I), which induced crystallisation. The reaction was then cooled to 00C and the product isolated by filtration. The filter cake was washed twice with a mixture of water (7.28 g) and isopropanol (4.68 g), then dried to afford the compound (I) (5.65 g, 55% yield); 1H NMR (400 MHz, DMSO-J6) delta ppm 1.79 (m, 2 H) 2.04 (m, 2 H) 2.38 (m, 2 H) 2.62 (d, J=4.5 Hz, 3 H) 2.74 (m, 2 H) 2.94 (s, 2 H) 3.93 (s, 3 H) 4.56 (tt, J=8.1, 3.8 Hz, 1 H) 7.21 (s, 1 H) 7.28 (m, 1 H) 7.50 (m, 2 H) 7.73 (q, J=4.5 Hz, 1 H) 7.81 (s, 1 H) 8.36 (s, 1 H) 9.56 (br.s, 1 H); Mass Spectrum: m/z (M + H)+ 474.2, 476.2.

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 2106-04-9.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BOARDMAN, Kay, Alison; CUNNINGHAM, Oliver, Robert; GOUNDRY, William; LAFFAN, David, Dermot, Patrick; WO2010/122340; (2010); A2;,
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Application of 15205-15-9, 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. 15205-15-9, name is 2-Chloro-6-fluorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 1 dram reaction vial was added 2-chloro-6-fluorobenzylamine (13.0 mg, 0.081 mmol 1.6 eq). A solution of HOAt (11.6 mg, 0.085 mmol, 1.7 eq) and carboxylic acid 1E (23 mg, 0.05 mmol, 1 eq) in 0.25 mL of 4:1 THF/DMF was added to the reaction vial (in the case of amine hydrochloride salts, diisopropylethylamine (30 mg, 0.23 mmol, 4.6 eq) was added). EDC (20 mg, 0.104 mmol, 2.1 eq) was then added and the reaction mixture sonicated for 1 minute. The reaction vial was shaken for 60 hours at room temperature following which a solution of LiOH.H2O (22 mg, 0.52 mmol, 10.5 eq) in 0.5 mL 1:1 MeOH/H2O was added and the mixture shaken for 12 hours.

The synthetic route of 2-Chloro-6-fluorobenzylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/298276; (2010); 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;,
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