Category: chlorides-buliding-blocks

Electric Literature of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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: 4-(6-(3-aminophenyl)-2,3-dihydroimidazo[2,l-b]thiazol-5-yl)-N-(4-(4-ethylpiperazin-l- yl)phenyl)pyrimidin-2-amine (compound of Step lh, 0.1 g) was dissolved in NMP and 2- naphthoyl chloride (42 mg, 0.220 mM) was added to the reaction mixture. The reaction mixture was stirred at RT for lh. The reaction mixture was diluted with diethyl ether, stirred for 5 min and ether was removed. The dilution of the reaction mixture with diethyl ether and removal of ether was repeated twice. The reaction mixture was further diluted with DCM and washed with aqueous saturated NaHC03. The organic layer was dried over anhydrous Na2S04, concentrated to yield crude product which was purified by flash column chromatography (silica gel, eluted with 6% MeOH in DCM) to afford the title compound ((4-(4-ethylpiperazin-l- yl)phenyl)amino)pyrimidin-4-yl)-2,3-dihydroimidazo[2, 1 -b]thiazol-6-yl)phenyl)-2-naphthamide. Yield: 0.069 g (53%); (0492) ‘H NMR (CDC13, 300 MHz): delta 8.56 (s, IH), 8.46 (s, IH), 8.19-8.17 (d, J=5.7 Hz, IH), 8.00-7.97 (m, 3H), 7.92-7.90 (d, J=6.6Hz, IH), 7.83 (s, IH), 7.62-7.58 (m, 2H), 7.50-7.47 (d, J=8.4 Hz, 2H), 7.42-7.36 (m, 3H), 6.92-6.89 (d, J=8.7 Hz, 2H), 6.74-6.72 (d, J=5.7 Hz, IH), 4.54-4.49 (t, J=6.9 Hz, 2H), 3.870-3.82 (t, J=6.9 Hz, 2H), 3.57 (m, 4H), 3.16 (m,4H), 2.54-2.52 (m, 2H), 1.17- 1.15 (t, J= 6.9Hz, 3H); MS: m/z 653.5 (M+l).The title compound was prepared in an analogous manner as the compound 1 of Example 1 involving reaction of 4-(6-(3-aminophenyl)-2,3-dihydroimidazo[2,l-b]thiazol-5-yl)-N-(4-(4- ethylpiperazin-l-yl)phenyl)pyrimidin-2-amine (Step lh of Example 1) with 3,5-difluorobenzene- 1 -sulphonyl chloride in DCM in the presence of pyridine at RT for lh. Yield: 75.7%; (0625) 1H NMR (DMSO-d6, 300 MHz): delta 10.57 (br s,lH), 9.58 (s, IH), 9.44 (s, IH), 8.19 (d, J=5.1 Hz, IH), 7.65 (d, J=12 Hz, IH), 7.57-7.55 (d, J=5.4 Hz, IH), 7.41 (s, IH), 7.33-7.17 (m, 6H), 6.95- 6.93 (d, J=5.7 Hz, 2H), 6.40-6.38 (d, J=6 Hz, IH), 4.59-4.55 (t, J=6 Hz, 2H), 4.19-4.17 (t, J=6 Hz, 2H), 3.7 (d, J=12 Hz, 2H), 3.21-3.13 (m, 5H), 2.90-2.80 (m, 3H), 1.25 (t, J=6 Hz, 3H); m/z 672.6 (M+l).

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GADEKAR, Pradip, Keshavrao; URUNKAR, Ganesh, Devidas; SEELABOYINA, Balapadmasree; DEKA, Nabajyoti; DAWANGE, Mahesh, Balasaheb; B-RAO, Chandrika; KHANNA, Smriti; WO2015/128698; (2015); A1;,
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Synthetic Route of 7149-75-9, 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 7149-75-9 as follows.

General procedure: (Z)-N-(3-Bromo-4-fluorophenyl )-N’-hydroxy-1H-indazole-7-carboximidamide (8a). To a solution of 7 (25 mg,0.105 mmol) in THF (1 mL) at 60 °C was 3-bromo-4-fluoroaniline (20 L, 0.105 mmol) was added andstirred for 10 min. A solution of NaHCO3 (13 mg, 0.157 mmol) in water (1 mL) was added dropwiseand stirred at 60 °C for 3 h. The mixture was extracted with EA and washed with brine. The organic layer was dried over MgSO4 and concentrated to obtain the crude mixture which was purified bycolumn chromatography (MPLC) to give compound 8a.

According to the analysis of related databases, 7149-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lee, Dong-Ho; Lee, Joo-Youn; Jeong, Jieun; Kim, Miok; Lee, Kyung Won; Jang, Eunseo; Ahn, Sunjoo; Lee, Chang Hoon; Hwang, Jong Yeon; Molecules; vol. 22; 11; (2017);,
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Adding a certain compound to certain chemical reactions, such as: 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, 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 7051-16-3, Recommanded Product: 7051-16-3

General procedure: An oven-dried 25 mL sealed tube was charged with PhI(OAc)2 (0.6 mmol), K3PO4 (1.2 mmol), BQ (0.1 mmol) and pre-activated 4A powdered molecular sieves (80 mg). The seal tube was evacuated and then refilled argon. Next, MeCN (0.5 mL), arene 4 (0.5 mmol) (if a liquid; if a solid, then substrate was added prior to the evacuation-refilled cycle), and CF3SiMe3 (1.2 mmol) were successively added. The seal tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 85 C for 6h. At the conclusion of the reaction, the mixture was allowed to cool to room temperature and filtered through a short pad of Celite, evaporated to remove the solvent. The residue was purified by flash column chromatography to give the desired product 5.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Wu, Xinyue; Chu, Lingling; Qing, Feng-Ling; Tetrahedron Letters; vol. 54; 3; (2013); p. 249 – 251;,
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Synthetic Route of 445-13-6, These common heterocyclic compound, 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline, 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.

Iodine monochloride (1.5 g) was added in one portion to a mixture of 3-chloro-4- trifluoromethylaniline (1.7 g), sodium acetate trihydrate (2.2 g), and acetic acid (10 ml) at room temperature. After 30 min aqueous sodium bicarbonate / sodium sulfite was added and the mixture extracted with diethyl ether. The organic phase was dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography (ethyl acetate – hexane) to afford the title compound, 2.2 g.

Statistics shows that 3-Chloro-4-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 445-13-6.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/36718; (2007); A2;,
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Some common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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. Computed Properties of C8H7ClF3N

Example 23 N-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2- pyridinyl)-4-imidazolidinecarboxamide (E23) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); A mixture of 3-methyl-2-oxo-1-(2-pyridinyl)-4-imidazolidinecarboxylic acid TFA salt (117 mg, 0.35 mmol), 1-hydroxybenzotriazole hydrate (80 mg, 0.525 mmol), 1-ethyl- 3-(3-dimethylaminopropyl)carbodiimide hydrochloride (101 mg, 0.525 mmol) and N- ethyl morpholine (0.224 ml, 1.75 mmol) in dichloromethane (8 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3- (trifluoromethyl)phenyl]methyl}amine (73.4 mg, 0.35 mmol) in dichloromethane (2 ml) was added and the reaction stirred at room temperature for 18 hours. The mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution. The organic phase was separated, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 0- 10% methanol in dichloromethane to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2-pyridinyl)-4- imidazolidinecarboxamide (90 mg, 62%). LC/MS [M+H]+ = 413, retention time = 2.55 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39226-96-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Chloride – Wikipedia,
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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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3BrCl2

Under a nitrogen atmosphere, tert-butyllithium (1.3 Msolution in Pentane, 17.8 mL, 23.2 mmol) was added dropwise to a solution of 3,5-dichlorobenzene (5.0 g, 22.1mmol) in tetrahydrofuran (50 mL) for 30 min and the reaction was continued for 2 hours. Trifluoroacetic anhydride is then added(2.56 g, 12.2 mmol) was added dropwise to the mixed solution and stirring was continued for 2 hours while maintaining at -78 ° C. Remove the cold, gradually rose toAfter room temperature, keep the reaction at room temperature for 2.5 hours. Saturated ammonium chloride solution (50 mL) was added to terminate the reaction. The mixture was extracted with etherThe organic phase was combined and washed with saturated brine (20 mL’2). The organic phase was separated and washed with anhydrous magnesium sulfateDrying, filtration, removal of the solvent, and distillation under reduced pressure gave a colorless transparent liquid 1 (2.58 g) in a yield of 48percent.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jingmen Pharmaceutical Industry Technology Institute; Wang Yong; Li Liwei; Hu Jianmei; Gu Dongyun; Huang Daoyou; (12 pag.)CN107353189; (2017); A;,
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Related Products of 104-11-0, 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. 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 22 (0.60 g, 3.85 mmol) and K2CO3 (0.71 g, 5.14 mmol) in anhydrous acetonitrile (150 mL) under N2 at 0 C, was added crude 21(o) (0.58 g, 2.57 mmol) and the reaction heated and allowed to progress under reflux for 6 h. Acetonitrile was then removed under reduced pressure and the reaction mixture worked up with ethyl acetate (100 mL) and saturated aqueous Na2CO3 (3 × 50 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography using mixtures of ethyl acetate:hexane (5:95) to (20:80) as eluent to give12(o)a as a yellow oil (0.45 g, 58%); 1H NMR (CDCl3, 400 MHz) delta 7.39-7.26 (9H, m, ArH), 4.55 (2H, s, H-1), 3.58 (2H, s, H-8), 3.50 (2H, s, H-10), 2.13 (3H, s, H-9); 13C NMR (CDCl3, 75 MHz) delta 137.4 (Arqu), 137.1 (Arqu), 134.7 (Arqu), 132.7 (Arqu), 130.7 (ArC-H), 130.2 (C-12/16), 129.6 (ArC-H), 128.3 (C-13/15), 128.1 (ArC-H), 127.7 (ArC-H), 61.5 (C-10), 59.9 (C-8), 52.0 (C-1), 41.9 (C-9). HRMS (ES): Found 301.1211 (M + H)+: C16H18ClN4 (M + H)+ requires 301.1215.

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, 1-(4-Chlorophenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zishiri, Vincent K.; Hunter, Roger; Smith, Peter J.; Taylor, Dale; Summers, Robert; Kirk, Kiaran; Martin, Rowena E.; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1729 – 1742;,
Chloride – Wikipedia,
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These common heterocyclic compound, 694-80-4, name is 1-Bromo-2-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. Application In Synthesis of 1-Bromo-2-chlorobenzene

REFERENCE EXAMPLE 10; 2-(2-Chlorophenyl)-6-methoxy-1 ,2,3,4-tetrahydroisoquinolin-1 -one; To a solution of 6-methoxy-1 ,2,3,4-tetrahydroisoquinolin-1-one (1.50 g, 8.5 mmol, obtained in reference example 9) in /V-methylpyrrolidone (4 ml_) under argon, 1- EPO bromo-2-chlorobenzene (2.34 g, 12.3 mmol), copper (I) iodide (0.33 g, 1.7 mmol) and potassium carbonate (2.33 g, 16.9 mmol) were added and the mixture was heated at 200 0C overnight. It was allowed to cool and CHCI3 and 1 N NaOH were added. The phases were separated and the aqueous phase was reextracted 2 times with CHCI3. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product thus obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 2.01 g of the desired compound (yield: 77%). LC-MS (method 1): tR = 8.05 min; m/z = 288.1/290.1 [M+Hf.

The synthetic route of 1-Bromo-2-chlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2007/337; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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 6775-78-6, Quality Control of 6-Chloroimidazo[1,2-b]pyridazine

Example 139 Production of 4-(imidazo[1,2-b]pyridazin-6-yloxy)aniline A mixture of 6-chloroimidazo[1,2-b]pyridazine (768 mg, 5.0 mmol), 4-aminophenol (818 mg, 7.5 mmol), potassium carbonate (2073 mg, 15.0 mmol) and N-methylpyrrolidone (5.0 mL) was stirred at 120 C. for 18 hr. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=70/30?0/100) and precipitated from diisopropyl ether to give the title compound (759 mg, 67%) as a gray powder. 1H-NMR (DMSO-d6, 300 MHz) delta 5.07 (2H, s), 6.60 (2H, d, J=8.9 Hz), 6.92 (2H, d, J=8.9 Hz), 7.00 (1H, d, J=9.8 Hz), 7.61 (1H, s), 8.01 (1H, s), 8.09 (1H, d, J=9.8 Hz).

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, 6-Chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); A1;,
Chloride – Wikipedia,
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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. 104-52-9, name is 3-Phenylpropyl Chloride, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

General procedure: Compounds A1-A20 were prepared following the previously reported method as described for A1 [1]. To a solution of 3-amino-5-mercapto-1,2,4-triazole (1.0 g, 8.61 mmol) in acetone was added sodium carbonate (1.37 g, 12.92 mmol) and alkyl halide (9.47 mmol). The mixture was then stirred at 60 oC for 3-6 h before cooling to room temperature. Upon completion of the reaction monitored by TLC, Na2CO3 were removed via filtration and the filtrate was evaporated under vacuum. The residue was purified by column chromatography, generating A1. 5-(((5-chlorobenzo[b]thiophen-3-yl)methyl)thio)-4H-1,2,4-triazol-3-amine, white solid, yield: 64 %.

The synthetic route of 104-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin; Chinese Chemical Letters; vol. 31; 2; (2020); p. 418 – 422;,
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