Category: chlorides-buliding-blocks

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 6579-54-0 as follows. 6579-54-0

(a) Step 1 [0256] A solution of 1H-indole-3-carboxaldehyde (0.290 g, 2.00 mmol) in methylene chloride (4 mL) was added with 2,6-dichlorophenylsulfonyl chloride (0.589 g, 2.40 mmol) and diisopropylethylamine (0.310 g, 2.40 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate to terminate the reaction, and then extracted three times with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 1-(2,6-dichlorophenylsulfonyl)-1H-indole-3-carboxaldehyde (0.658 g, 93%).1H NMR (300 MHz, CDCl3) delta 7.32-7.38 (m, 2H), 7.41-7.45 (m, 1H), 7.48-7.51 (m, 2H), 7.63-7.67 (m, 1H), 8.28-8.31 (m, 1H), 8.41 (s, 1H), 10.18 (s, 1H).

According to the analysis of related databases, 6579-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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. 26487-67-2.

General procedure: A mixture of riccardin D, alkyl chloride hydrochloride and potassium carbonate in acetone was stirred under reflux for 24h. The insoluble material was then filtered off and the filtrate was concentrated to provide the residue that was purified by flash column chromatography, eluting with a gradient mixture of MeOH/ EtOAc/aqueous ammonia (93:5:2 to 80:18:2, V/V), to yield the pure product (compounds 17a-17f and 18a-18f) as a solid in good yield.

The synthetic route of 1-(2-Chloroethyl)azepane hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Bin; Liu, Jun; Gao, Yun; Zheng, Hong-bo; Li, Lin; Hu, Qing-wen; Yuan, Hui-qing; Lou, Hong-xiang; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 603 – 618;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13726-14-2, name is 4-Chloro-3-methoxyaniline, 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. 13726-14-2

General procedure: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below. 2-Chloro-/Y4-(4-chloro-3-methoxyphenyl)-5-methylpyrimidin-4-amine (SG1-173-01): This was prepared from 2,4-dichloro-5-methylpyrimidine (1.00 g), 4-chloro-3- methoxyaniline (1.02 g), and DIPEA (1.28 mL) using procedure B (reaction time, 13 h). The solvent was removed and EtOAc (40 mL) was added. The organic layer was extracted with water (40 mL). The aqueous layer was re-extracted with EtOAc (40 mL). The organic layers were combined, washed with water and brine (40 mL each), dried (Na2S04), and concentrated under reduced pressure. The resulting residue was purified via column chromatography (S1O2) eluting with hexanes/EtOAc (0: 10 to 4:6 v/v) to give the title compound as an off-white solid (0.530 g, 30%). Mp: 132-134 C. NMR (400 MHz, DMSO-ifc): delta 8.90 (s, 1H, disappeared on D20 shake), 8.07 (s, 1H), 7.54 (s, 1H), 7.38 (d, / = 8.7 Hz, 1H), 7.33 (d, / = 8.7 Hz, 1H), 3.83 (s, 3H), 2.16 (s, 3H). HPLC-MS (ESI+): m/z 286.1 [70%, (M35C137C1+H)+], 284.1 [100%, (M35C135C1+H)+].

Statistics shows that 13726-14-2 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-methoxyaniline.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 36556-52-2, name is 2,3-Dichloro-4-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 36556-52-2, 36556-52-2

Acetone (7.95 mL, 107 mmol) is added to a solution of 2,3-dichloro-4-fluoroaniline (1.93 g, 10.7 mmol) in DMSO (20 mL). Palladium(ll)acetate (0.481 g, 2.14 mmol) and copper(ll) acetate (5.84 g, 32.2 mmol) are added, and the mixture is heated at 85C for 17h. The mixture is concentrated, filtered over a plug of silica and rinsed with DCM. The filtrate is washed with HCI 2N and brine, dried over MgSC and concentrated. The residue is purified by FC, eluting with heptane / EtOAc from 100:0 to 95:5, affording the title compound as an orange solid (0.52 g, 23%). LC-MS A: tR = 0.92 min; [M+H]+ = 218.07.

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, 2,3-Dichloro-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; FRETZ, Heinz; LYOTHIER, Isabelle; POTHIER, Julien; RICHARD-BILDSTEIN, Sylvia; SIFFERLEN, Thierry; WYDER PETERS, Lorenza; POZZI, Davide; CORMINBOEUF, Olivier; (306 pag.)WO2017/85198; (2017); A1;,
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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, A new synthetic method of this compound is introduced below., 33863-76-2

To a mixture of 8-(l-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6- carboxamide (350 mg, 1.01 mmol, single enantiomer, [a]D2o: +35 in acetonitrile), cesium carbonate (1288 mg, 3.95 mmol), (9,9-dimethyl-9H-xanthene-4,5- diyl)bis(diphenylphosphine) (147 mg, 0.25 mmol) and l-bromo-3-chloro-5-fluorobenzene (467 mg, 2.23 mmol) in degassed 1,4-dioxane (2ml), was addedtris(dibenzylideneacetone)dipalladium (70 mg, 0.08 mmol). The suspension was heated in a sealed container at 95C for 16 hrs. The reaction mixture was filtered through a short pad of dicalite and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 0 to 8% isopropanol in DCM. The solvent was evaporated to dryness, the product triturated with diethyl ether – DCM (9: 1), collected by filtration and dried to afford 8-(l-(3-chloro-5-fluorophenylamino)ethyl)-N,N- dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (320 mg; 67%) as a clear yellow solid. Mass Spectrum: M+H+ 474. [a]D20: -138. NMR Spectrum (DMSOd6): 1.52 (d, 3H), 2.75 (bs, 3H), 2.95 (bs, 3H), 3.49-3.63 (m, 4H), 3.70-3.79 (m, 4H), 4.98-5.07 (m, 1H), 5.60 (s, 1H), 6.23 (d, 1H), 6.42 (d, 1H), 6.43 (ddd, 1H), 6.94 (d, 1H), 7.54 (d, 1H), 7.80 (d, 1H).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard, Christophe; DEGORCE, Sebastien, Louis; LAMBERT-VAN DER BREMPT, Christine, Marie, Paul; MORGENTIN, Remy, Robert; PLE, Patrick; WO2011/51704; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 626-43-7, name is 3,5-Dichloroaniline, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 626-43-7

General procedure: To a solution of substituted aniline 22a-i (0.81 mmol) and triethylamine (0.89 mmol) in DCM (2 mL) at 0 C was added bromoacetyl bromide (0.81 mmol) dropwise over 15 min, and stirring was continued for an additional 1 h at 0 C. The mixture was dilutedwith DCM (10 mL), washed with HCl (2 10 mL), H2O (1 10 mL),sat. aqueous NaHCO3 (1 10 mL), brine (1 10 mL), dried (Na2SO4),and the solvent removed in vacuo to give bromoacetamides 21a-i.

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, 626-43-7, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hung, Joy M.; Arabshahi, Homayon J.; Leung, Euphemia; Reynisson, Johannes; Barker, David; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 420 – 437;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

57946-56-2, 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. 57946-56-2, name is 4-Chloro-2-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 5 Preparation of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide A solution of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in acetic acid is refluxed for 2 hours, treated with additional 4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extract is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuoto obtain a purple oil. Flash column chromatography of the oil using silica gel and 15 to 20% ethyl acetate in hexanes solutions gives the title product as an off-white solid (25.3 g, 69% yield, mp 81-82C) which is identified by 1H, 13C and 19F NMR spectral analyses.

The synthetic route of 4-Chloro-2-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; EP985670; (2000); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

41965-95-1, Adding a certain compound to certain chemical reactions, such as: 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, 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 41965-95-1.

l-(10-((3-chloro-4-methoxybenzyl)amino)-3,4-dihydrobenzo[][l,6]naphthyridin- 2(lH)-yl)ethan-l-one, I [00241] A solution of 30 (1.15 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (3.45 mmol), Nal (0.06 mmol), and triethylamine (3.45 mmol) in NMP (5.0 mL) was heated at 130 C for 6 h. The solvent was evaporated off and the residue was purified by Flash Chromatography (AcOEt: MeOH 8:2) to give I. MS ESI (m/z) 396 (M+H)+; 1H NMR (400 MHz, CDC13) delta 8.05- 8.02 (m, IH), 7.92 (d, IH, J=9.2 Hz), 7.67-7.63 (m, IH), 7.45-7.40 (m, IH), 7.35 (d, IH, J=2.4 Hz), 7.22 (dd, IH, Ji=2.0, J2=8.4 Hz), 6.92 (d, IH, J=8.4 Hz), 4.75 (s, 2H), 4.65 (d, 2H, J=5.2 Hz), 3.90 (s, 4H), 3.81 (t, 2H, J=6.0 Hz), 3.27 (t, 2H, J=6.4 Hz), 2.20 (s, 3H).

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-4-methoxybenzylamine Hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

461-81-4, 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. 461-81-4, name is 1-Chloro-4-(trifluoromethoxy)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. 4-Chloro-2-nitro-1 -trifluoromethoxy-benzene and 1 -Chloro-2-nitro-4- trifluoronnethoxy-benzeneTo a mixture of i-chloro-4-trifluoromethoxy-benzene (9.24 g, 47 mol) in cone. H2SO4 (30 ml_) at 00C is added cone. HNO3 (10 ml_) dropwise over a 5 min period. After the mixture is stirred at 0 0C for 1 h, it was poured into ice. More H2O is added, and the resulting mixture is extracted with EtOAc. The organic extract is washed with H2O (3X) and brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 10.87 g (95%) of the product as a mixture of 1 -chloro-2-nitro-4-trifluoromethoxy-benzene and 4-chloro-2-nitro-1-trifluoromethoxy-benzene (-50/50, based upon 19F NMR). 1H NMR (CDCI3): delta 8.05-7.95 and 7.85-7.70 (m, 1 H), 7.70-7.55 and 7.50-7.35 (m, 2H); 19 F NMR (CDCI3) delta -57.32 and -57.84 (s, 3F), -109.07 and -117.90 (t, J = 6.2Hz and d, J = 6.2 Hz, 1 F).

The synthetic route of 1-Chloro-4-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; CHOI-SLEDESKI, Yong-Mi; GARDNER, Charles, J.; LIANG, Guyan; POLI, Gregory, B.; SHUM, Patrick, Wai-Kwok; STOKLOSA, Gregory, T.; ZHAO, Zhicheng; WO2011/22449; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 933190-51-3 name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 2,2-dimethylpyrrolidine (0.248 g, 2.5 mmol) in DMF (8 mL) was added NaH (0.060 g, 60% dispersion in mineral oil, 2.5 mmol) and stirred for 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.233 g, 1 mmol) under N2. The mixture was stirred at room temperature for 16 h. Then it was partitioned between 15 mL of saturated NH4Cl solution and 15 mL of ether. The organic layer was washed with water (10 mL¡Á3) and saturated NaCl solution (10 mL¡Á3), dried over NaSO4, concentrated in vacuo, and purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 6-chloro-8-(2,2-dimethylpyrrolidin-1-yl)imidazo[1,2-b]pyridazine (0.140 g, 22%) as a light brown solid. LC-MS: [M+H]+, 251.1, tR=1.698 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics