Tag: M.W=100-200

Application of 33406-96-1, These common heterocyclic compound, 33406-96-1, name is 1-Chloro-4-fluoro-2-methylbenzene, 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 solution of 2-chloro-5-fluorotoluene (5.0 g) in acetic anhydride (40 ml) was added dropwise under ice-cooling concentrated sulfuric acid (40 ml), and then added dropwise a solution of anhydrous chromic acid (9.3 g) in acetic anhydride (40 ml) for 2 hours. The mixture was stirred at the same temperature for 1 hour, poured into ice-water and extracted with diethylether. The organic layer was washed with sodium carbonate solution, water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in tetrahydrofuran (10 ml). To the mixture were added water (4 ml) and concentrated sulfuric acid (4 ml), and the mixture was stirred at 100 C. for 30 minutes and cooled. The reaction solution was extracted with ethyl acetate. The organic layer was washed with sodium carbonate solution, water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give the residue, which was subjected to silica gel column chromatography to give 2-chloro-5-fluorobenzaldehyde (1.6 g). The similar reaction was repeated to give 2-chloro-5-fluorobenzaldehyde (1.2 g). In water (55 ml) was dissolved sodium hydroxide (0.78 g), and to the mixture was added acetone (55 ml), and then added dropwise a solution of 2-chloro-5-fluorobenzaldehyde (2.8 g) in acetone (10 ml). The reaction solution was stirred at room temperature for 2 hours, and acetone was evaporated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and concentrated under reduced pressure to give 4-(2-chloro-5-fluorophenyl)-3-buten-2-one (0.24 g). To a solution of 20% sodium ethoxide in ethanol (0.43 g) was added at room temperature diethyl malonate (0.2 g), and then added little by little 4-(2-chloro-5-fluorophenyl)-3-buten-2-one (0.24 g). The mixture was stirred at room temperature for 30 minutes, refluxed for 2 hours and cooled, and the solvent was evaporated. The residue was dissolved in water, and the aqueous layer was washed with ethyl acetate and concentrated. To the reside was added 2M sodium hydroxide (0.7 ml), and the mixture was refluxed for 2 hours cooled. To the mixture was added 2.5M sulfuric acid (0.7 ml), and the mixture was refluxed for 15 minutes. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(2-chloro-5-fluorophenyl)cyclohexane-1,3-dione (0.17 g) as oil. A solution of 5-(5-chloro-2-fluorophenyl)cyclohexane-1,3-dione (0.17 g) and ammonium acetate (0.16 g) in ethanol (10 ml) was refluxed for 12 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with sodium carbonate solution, water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethanol (3.5 ml) and toluene (6 ml). To the mixture were added 3-oxobutylaldehydedimethylacetal (0.21 g) and powdery potassium hydroxide (34 mg), and the mixture was refluxed. To the mixture was added powdery potassium hydroxide (0.07 g) 30 minutes later; powdery potassium hydroxide (0.07 g) and 3-oxobutylaldehydedimethylacetal (17 mg) 1 hour later; and powdery potassium hydroxide (0.07 g) 1.5 hours later. Then, the mixture was stirred at the same temperature for 2 hours and cooled. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. Under reduced pressure, ethyl acetate was evaporated, and the residue was subjected to silica gel column chromatography(ethyl acetate-hexane) to give 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one. To a solution of 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one in ethanol (10 ml) were added aminoguanidine hydrochloride (0.041 g), concentrated hydrochloric acid (0.078 ml) and water (0.078 ml), and the mixture was refluxed for 4 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added water. The aqueous layer was washed with ethyl acetate, and to the aqueous layer was added sodium hydrogen carbonate solution to make it alkaline. The solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in 1N hydrochloric acid (1 ml) and concentrated to give crystals, which were recrystallized from ethanol-ethyl acetate to give 7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 170) (0.05 g) as colorless crystals. mp. 268 C. (decomp.). 1H-NMR(DMSO-d6) delta: 2.76-3.05 (1H, m), …

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6350749; (2002); B1;,
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Related Products of 39191-07-6, 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 39191-07-6 as follows.

General procedure: To a solution of 2,6-bis(chloromethyl)pyridine (1 mmol) in anhydrous acetonitrile (10 mL) was added cesium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 5 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (100:1, v/v) to give the title compound as a colorless liquid or a white solid.

According to the analysis of related databases, 39191-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Liu, Shuangping; Gaines, Theresa; Oum, Yoonhyeun; Shi, Qi; Mooring, Suazette Reid; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 340 – 350;,
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Application of 93-50-5, These common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, 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.

Stepl[00173j To a stirred solution of Intermediate 1(0.25 g, 1.22 mmol) in DMA (3 mL) was added 4-chloro-2-methoxyaniline (0.25 g, 1.58 mmol) followed by NaHMDS (1M in THF, 3.66 mL, 3.66 mmol). The reaction was stirred for 20 minutes and then water was gradually added resulting in the product crashing out as a precipitate. The product was collected by filtration, washed with additional water and then dried under vacuum providing Intermediate 12 (361 mg, 91% yield). LC retention time 3.44 mm [A].

The synthetic route of 93-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; LIN, Shuqun; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; WO2014/74660; (2014); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloro-2-fluoroaniline

General procedure: N,N-Carbonyldiimidazole (0.17 g, 1.2 mmo1) was added to a solution of 8 (0.21 g, 1 mmo1) in anhydrous tetrahydrofuran (THF) and the mixture was stirred for 10 min at room temperature under a nitrogen atmosphere. Subsequently, substituted aniline or phenylethylamine (1.2 mmol) was slowly added to the mixture. The mixture was stirred at 80 oC overnight, then filtrated. The filtrate was evaporated under reduced pressure to give an oil or colored solid, which was purified by column chromatography with petroleum ether/ethyl acetate (7 : 1) to obtain the desired product 9a-9g.

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:
Article; Liu, Yang; Li, Yijing; Liu, Jianzhen; Yang, Limin; Li, Pengzhan; Zhao, Guisen; Letters in drug design and discovery; vol. 13; 4; (2016); p. 314 – 323;,
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Synthetic Route of 7006-52-2, 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 7006-52-2 as follows.

Sodium hydride (4.89 g, 73.4 mmol, 60percent in oil) was added portionwise to an ice-cooled solution of N-methyl-3-chloroaniline (8 g, 56.5 mmol) in DMF (40 ml). This mixture was5 then added to an ice-cooled solution of 2,4-dichloropyrimidine (16.8 g, 113 mmol) in DMF (40 ml). The resulting mixture was heated at 700C for 18 hrs. Additional sodium hydride (large excess) was added and the mixture was heated at 1000C for 2 hrs.. After cooling, the mixture was poured in saturated aqueous sodium bicarbonate and extracted with DCM. The organic layer was dried over magnesium sulfate and filtered. After evaporation of the o solvents, the residue was purified by chromatography on silica gel (eluant: 0 to 20percent EtOAc in DCM, then 10percent methanol in EtOAc ) to give 4-[(3-chlorophenyl)-methyl- ammo]-lH-pyrimidin-2-one as a light brown solid (4 g, 30percent). NMR Spectrum: (DMSOd6 and CF3CO2D) 3.53 (s, 3H), 7.46 (m, IH), 7.67-7.60 (m, 3H), 7.78 (m, IH); Mass spectrum: MH+ 236

According to the analysis of related databases, 7006-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/104754; (2008); A1;,
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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 6775-78-6 as follows. category: chlorides-buliding-blocks

In a 500 ml single-necked round bottom flask was added3-Amino-6-chloropyridazine(38.86 g, 300 mmol), 40% aqueous chloroacetaldehyde (58.88 g, 300 mmol), sodium bicarbonate (30.24 g, 360 mmol) and 260 mLTert-butanol, start magnetic stirrer, the reaction flask was stirred at 80 C for 7 hours.TLC detection of raw materials 3-amino-6-chloropyridazine reaction is completed,Nitric acid (22.68 g, 360 mmol) was added and reacted for a further 4 hours with stirring.TLC and GC analysis confirmed that the intermediate 6-chloroimidazo [1,2-b] pyridazine was completely reacted. The reaction mixture was suction filtered and the filter cake was recrystallized from ethyl acetate: n-hexane = 1: 3 to give the pure product 3-nitro-6-chloroimidazo [1,2-b] pyridazine. The filtrate was extracted with ethyl acetate , The extract was removed by rotary evaporation to give the crude product, which was recrystallized from ethyl acetate: n-hexane = 1: 3 to obtain the pure product3-nitro-6-chloroimidazo [1,2-b] pyridazine,After drying, the yield was calculated 86.30%, purity 99.31%

According to the analysis of related databases, 6775-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Youbang Biochemical Technology Co., Ltd.; Geng Xuanping; Lai Chao; Lai Ziteng; Lai Xinsheng; (6 pag.)CN106632353; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Application In Synthesis of (4-Chloro-3-fluorophenyl)methanamine

A mixture of Example 477A (61.7 mg, 0.128 mmol), (4-chloro-3- fluorophenyl)methanamine (0.019 mL, 0.153 mmol), and triethylamine (0.021 mL, 0.153 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 50 C for 3 hrs. After cooling, the reaction mixture was treated with brine and extracted with ethyl acetate (2x). The combined organic layers were dried over MgSO/t, filtered, and concentrated. The residue was purified by reverse- phase HPLC (see protocol in Example 112D) to provide the title compound (23.7 mg, 35%).JH NMR (400 MHz, DMSO-<) delta ppm 7.50 (dt, J = 14.5, 8.4 Hz, 2H), 7.26 - 7.15 (m, 2H), 7.11 - 7.00 (m, 2H), 6.83 (ddd, J = 8.9, 2.8, 1.1 Hz, 1H), 6.18 (t, J = 6.1 Hz, 1H), 5.74 (s, 1H), 5.02 (d, J = 4.4 Hz, 1H), 4.46 (s, 2H), 4.14 (d, J = 6.1 Hz, 2H), 4.01 (dt, J = 8.5, 3.8 Hz, 1H), 2.23 (ddd, J = 12.6, 9.4, 2.8 Hz, 1H), 2.12 - 1.98 (m, 1H), 1.95 - 1.63 (m, 8H); MS (ESI+) m/z 528.2 (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, (4-Chloro-3-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
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Synthetic Route of 39226-95-4, These common heterocyclic compound, 39226-95-4, name is 2,3-Dichlorobenzylamine, 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 260 N-(2,3-dichlorobenzyl)-2-(5-isoquinolinyl)propanamide The title compound was prepared using the procedure described in Example 222B using 2,3-dichlorobenzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 359 (M+H)+; MS (ESI-) m/z 357 (M-H)-; 1H NMR (DMSO, 300 MHz) delta 1.54 (d, J 7.1, 3H), 4.20 (m, 2H), 4.53 (q, J 7.1, 1H), 7.17 (d, J 7.8, 1H), 7.26 (t, J 7.8, 1H), 7.52 (d, J 8.1, 1H), 7.78 (t, J 7.8, 1H), 7.91 (d, J 6.5, 1H), 8.16 (d, J 8.1, 1H), 8.24 (d, J 6.4, 1H), 8.59 (d, J 6.2, 1H), 8.66 (t, J 5.8, 1H), 9.50 (s, 1H).

The synthetic route of 39226-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2004/157849; (2004); 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Step (2) : Preparation of 1, 3-benzodioxol-5-ylmethvl methyl sulfone 9.7 g of 5- (chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetraliydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C, and reacted for 10 minutes. The reactant was then heated to 50C and reacted for 1 hour. The reaction mixture was cooled to 0C and then slowly added to a flask containing [1, 3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 5 ml methane sulfonyl chloride, the mixture was reacted for 30 minutes, and the reactant was heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column cluomatography using ethyl acetate: n-hexane (1: 3), to give 0.75 g of the title compound of the following formula la (Rf: 0.35, Yield: 5%). [Chemical Formula 1 a] The compound was dissolved in CDC13 and TMS and then characterized by’H NMR spectroscopy. The result is as follows; ‘H NMR 6 : 2.75 (s, 3H), 4.14 (s, 2H), 5.97 (s, 2H), 6.81-6. 88 (m, 3H).

The synthetic route of 20850-43-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); A1;,
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Reference of 4863-91-6, 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. 4863-91-6, name is 3-Chloro-5-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j00196j To 4-chlorophenacyl chloride (1.0 g, 5.3 mmol) in anhydrous acetonitrile (15 mL) under a nitrogen atmosphere was added potassium thiocyanate (0.57 g, 5.8 mmol). The suspension was stirred at ambient temperature for 2.5 hours. Next, to the suspension was added 3-chloro-5-fluoroaniline (0.85 g, 5.8 mmol), and the resulting mixture was stirred at ambient temperature for 2 hours. Then, water (30 mL) was slowly added to the reaction mixture, and the resulting mixture was slurried for 20 minutes. The solids were collected by filtration and washed with water then dried in vacuo to yield the title compound (1.72 g, 9 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-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYCERA CORPORATION; HURD, Alexander, R.; TAYLOR, Clarke, B.; TOOGOOD, Peter, L.; VAN HUIS, Chad, A.; WO2013/185046; (2013); A1;,
Chloride – Wikipedia,
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