Tag: M.W=100-200

Application of 4152-90-3,Some common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, molecular formula is C7H8ClN, 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: To a mixture of 5a (435mg, 1mmol), HATU (760mg, 2mmol), HOAt (272mg, 2mmol), substituted amine (1.2mmol) and DCM (10mL) at 0°C was added DIPEA (0.52mL, 3mmol), and the reaction mixture was then slowly warm to room temperature and stirred overnight. The reaction was quenched by water and the mixture was extracted with ethyl acetate, washed with water and brine, dried over Na2SO4 and then subjected to flash chromatography

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chlorophenyl)methanamine, its application will become more common.

Reference:
Article; Gao, Yang; Zhang, Peng; Cui, Anfeng; Ye, De-Yong; Xiang, Meng; Chu, Yong; Bioorganic and Medicinal Chemistry; vol. 26; 20; (2018); p. 5479 – 5493;,
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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. 102-49-8, name is 3,4-Dichlorobenzylamine, A new synthetic method of this compound is introduced below., Quality Control of 3,4-Dichlorobenzylamine

General procedure: To a solution of the appropriate acid derivative (1 mmol) in dryDMF (5 mL) O-benzotriazol-1-yl-N,N,N’,N’-tetramethyluroniumhexafluorophosphate (HBTU, 2 mmol) was added followed by 1-hydroxybenzotriazole (HOBt, 1 mmol), diisopropylethylamine (DIPEA, 1.5 mmol) and the appropriate amine (1.2 mmol). The mixture was stirred under N2 atmosphere at room temperature for 30 min and DIPEA (1.5 mmol) was added again. The reaction mixture was stirred at room temperature for 18 h, poured into water and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated to dryness. The crude product, unless otherwise indicated, was recrystallized from EtOH.#10;

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; Pasquini, Serena; De Rosa, Maria; Ligresti, Alessia; Mugnaini, Claudia; Brizzi, Antonella; Caradonna, Nicola P.; Cascio, Maria Grazia; Bolognini, Daniele; Pertwee, Roger G.; Di Marzo, Vincenzo; Corelli, Federico; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 30 – 43;,
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Application of 1435-44-5, A common heterocyclic compound, 1435-44-5, name is 1-Chloro-2,4-difluorobenzene, molecular formula is C6H3ClF2, 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.

1-(3-Chloro-2,6-difluoro-phenyl)-carboxaldehyde was prepared from 3-Chloro-2,6-difluorobenzene with lithium diisopropylamide and N,N-dimethylformamide in a method similar to A. S. Cantrell, et al., J. Medicinal Chemistry 1996, 21,4261

The synthetic route of 1435-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US6342497; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10272-06-7, name is 3-Chloro-5-methoxyaniline, 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 10272-06-7, Recommanded Product: 10272-06-7

General procedure: To a solution of ethyl 4-bromo-1H-indole-2-carboxylate in toluene underargon atmosphere was added Pd2(dba)3 (0.1 eq), DavePhos (0.2 eq), K3PO4 (3 eq, 1Maqueous solution) and aryl amine (3 eq), and then the mixture was reacted at 80 Cuntil the starting material disappeared. The mixture was cooled to room temperatureand concentrated. Ethyl acetate was added to dissolve the residue and the mixture waswashed with saturated brine and water, dried over anhydrous Na2SO4, andconcentrated in vacuo. The crude product was purified by column chromatography toafford the target compound. Compounds 8a-8f, 8i-8l, 8a-1, 8a-6 ~ 8a-11, 8a-14 wereprepared with method 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-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cui, Guonan; Lai, Fangfang; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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Application of 39989-43-0, The chemical industry reduces the impact on the environment during synthesis 39989-43-0, name is 3,5-Dichlorobenzylamine, I believe this compound will play a more active role in future production and life.

Example 124: Synthesis of 4-Chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-l- one; A mixture 6-bromo-4-chloro-2H-phthalazin-l-one (97mg, 0.374 mmol), 3,5- dichlorobenzylamine (0.057mL, 0.424 mmol), Pd2(dba)3 (29mg, 0.032 mmol), rac- BINAP (70mg, 0.112 mmol) and NaO’Bu (104mg, 1.08 mmol) in DMA (5mL) was heated at 8O0C for 1.5h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(3,5-dichloro -benzylamino)-2H-phthalazin-l-one (3 mg) as a white solid, 1H (400 MHz, CDCl3) delta: 4.40 (s, 2H), 6.84 (m, IH), 6.99 (m, IH), 7.22 (m, 3H), 8.14 (m, IH), 10.80 (s, IH) ppm; m/z (M+l) 353.83.

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, 3,5-Dichlorobenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-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 2106-04-9, Safety of 3-Chloro-2-fluoroaniline

Step 1: 6-Acetoxy-4-(3-chloro-2-fluoroanilino)-7-methoxycluinazoline hydrochloride6-Acetoxy-7-methoxyquinazolin-4-one (International Patent Application WO 96/15118, Example 39 thereof; 21.4 kg, 89.3 mol) was suspended in toluene (150 kg). To this was added N-ethyldiisopropylamine (13.3 kg, 103 mol). The brown suspension was heated to 70 C. then phosphorus oxychloride (36.0 kg, 228 mol) was charged. The reaction mixture was stirred at 70 C. for 5 hours. Further toluene (84.0 kg) was added followed by 3-chloro-2-fluoroaniline (14.88 kg, 102 mol). The reaction mixture was stirred at 70 C. for 2 hours during which time a solid precipitated. The suspension was cooled to 25 C. and held at this temperature for 93 hours. The reaction mixture was filtered and the filter cake washed with toluene (2×55.5 kg). The cake was further washed with a mixture of ethanol (24.5 kg) and water (32.0 kg) twice, then ethanol (50.5 kg) twice and the solid then dried under vacuum to give the title product as a beige solid (33.4 kg, 78%); 1H NMR: 2.37 (s, 3H), 4.00 (s, 3H), 7.34 (ddd, 1H), 7.48 (s, 1H), 7.52 (ddd, 1H), 7.61 (ddd, 1H), 8.62 (s, 1H), 8.86 (s, 1H); Mass Spectrum: 362.4, 364.4.

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-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2009/286982; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-02-7,Some common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, 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 mixture of (S)-1-(1-(3-chlorophenyl)-2-hydroxyethyl)-3-(1-(2-chloropyrimidin-4-yl)-1H-pyrazol-4-yl)urea (0.02 g, 0.05 mmol), 2-chloro-4-fluoroaniline (0.009 g, 0.6 mmol), potassium carbonate (0.01 g, 0.075 mmol), and dioxane (2 mL) in a glass tube was purged with nitrogen gas for 20 min. Tris(dibenzylideneacetone)dipalladium(0) (0.002 g, 0.0025 mmol) and BINAP (0.003 g, 0.005 mmol) were added to the reaction mixture, which was purged with nitrogen gas for another 15 min. The tube was sealed and heated at 90 C. for 4 hours. Reaction mixture was filtered through Celite, and filtrate was evaporated; residue was suspended in water, and extracted with ethyl acetate. Organic layer was dried over sodium sulfate, evaporated, and the residue was purified by column chromatography over silica gel using 60% ethyl acetate in hexanes as eluent to give (S)-1-(1-(2-((2-chloro-4-fluorophenyl)amino)pyrimidin-4-yl)-1H-pyrazol-4-yl)-3-(1-(3-chlorophenyl)-2-hydroxyethyl)urea (0.003 g, 12%). 1HNMR (400 MHz, CDCl3, plus a few drops MeOD): 8.50 (s, 1H), 8.33 (d, J=5.2 Hz, 1H), 8.27-8.25 (m, 1H), 7.51 (s, 1H), 7.28-7.19 (m, 1H), 7.23-7.12 (m, 3H), 7.12-7.10 (m, 1H) 7.04-6.99 (m, 1H), 6.23 (d, J=6.8 Hz, 1H) 4.87-4.84 (m, 1H), 3.81-3.77 (m, 1H), 3.64-3.61 (m, 1H). LC-MS calcd exact mass 501.09, found m/z 502.3 [M+H]+. HPLC purity 98.17%.

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); A1;,
Chloride – Wikipedia,
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Electric Literature of 2687-12-9, A common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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 1Obtaining 2- (3-N,N-diisopropylamine-l-phenylpropyl) -A- carboxyphenol (IVa)(IVa) Diisopropylamine (2.77 1, 19.65 mol) and sodium iodide(16.95 g, 0.13 mol) were loaded onto a solution of cinnamyl chloride (1 kg, 6.55 mol) in ethanol (3 I/kg) at 20/250C. The mixture was heated at internal 80-850C, the reaction conditions being maintained for 3-4 hours until the end of such reaction.The mixture was cooled at 40-450C and distilled to an internal volume of 1.3 1. The mixture was then cooled at 20- 25C, water (4 1) and toluene (3 1) was added and the pH was adjusted to 1.0-1.5. The phases were decanted and dichloromethane (4 1) was loaded onto the aqueous phase, adjusting the pH again to 11.5-12.0. The phases were decanted and the organic phase was washed with water (4 1) . Once the phases were decanted, the organic phase was distilled at atmospheric pressure to an internal volume of 1.3 1 in order to then load heptane (0.5 1) . Again, it was distilled to 1.3 1 and heptane (2 1) was loaded.The suspension which was obtained was filtered by a prelayer, which was washed with heptane (0.5 1) . The filtered organic phase was distilled at atmospheric pressure to an internal volume of 1.3 1.The amine content of the reaction mixture was determined by the potentiometric titration thereof.

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAGACTIVES, S.L.U.; LORENTE BONDE-LARSEN, Antonio; MARTIN PASCUAL, Pablo; LADERAS MUNOZ, Mario; GUTIERREZ FUENTES, Luis Gerardo; WO2011/12584; (2011); A1;,
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Application of 3972-56-3, These common heterocyclic compound, 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, 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.

100 ml of 60% nitric acid was added dropwise to 100 ml of 95% sulfuric acid at a temperature of 35C or less, under ice-cooling, to prepare a mixed acid solution. 100 g (0.593 mol) of 4-tert-butylchlorobenzene (A-1) was added dropwise to this mixed acid solution, at a temperature of 30C or less, followed by after-reaction (20 to 25C) for 2.5 hours. The reaction solution was poured into cold water, and it was then extracted with 100 ml of toluene, followed by washing with water, to obtain a toluene solution of (A-2).

The synthetic route of 3972-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; EP1535898; (2005); 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. 104-52-9, name is 3-Phenylpropyl Chloride, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Phenylpropyl Chloride

6-amino-1-ethylbenzo[cd]indol-2(1H)-one can refer to Example 1. A reaction mixture of 6-amino-1-ethylbenzo[cd]indol-2(1H)-one (100 mg, 0.47 mmol) and (3-chloropropyl)benzene (73 mg, 0.47 mmol) in CH3CN (20 mL) was stirred at rt. K2CO3 (195 mg, 1.41 mmol) was added to the reaction mixture, and stirred at 70 C. for overnight. The reaction mixture was extracted with ethyl acetate (150 mL*2). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography with petroleum ether/ethyl acetate (5/1, v/v) to yield 1-ethyl-6-((3-phenylpropyl)amino)benzo[cd]indol-2(1H)-one (60 mg, 38%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.06 (d, J=7.2 Hz, 11H), 7.84 (d, J=8.0 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 7.32 (t, J=7.6 Hz, 2H), 7.26-7.04 (m, 3H), 6.77 (d, J=7.6 Hz, 1H), 6.34 (d, J=7.2 Hz, 1H), 4.24 (s, 1H), 3.94 (q, J=7.2 Hz, 2H), 3.30 (t, J=6.8 Hz, 2H), 2.83 (t, J=7.2 Hz, 2H), 2.21-2.03 (m, 2H), 1.36 (t, J=7.2 Hz, 3H).

According to the analysis of related databases, 104-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Institutes of Biomediciene and Health, Chinese Academy of Sciences; XU, Yong; XUE, Xiaoqian; ZHANG, Yan; SONG, Ming; (42 pag.)US2018/8574; (2018); A1;,
Chloride – Wikipedia,
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