Author: tianli

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,
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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

A common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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. 626-43-7.

General procedure: Substituted aniline 4a-4s (50 mmol) was dissolved in the 50 mL HCl (18%, aqueous) in the icebath. NaNO2 (50 mmol) dissolved in 50 mL water was added dropwise. The reaction mixture wasstirred for 1 h to obtain a clear solution. Then the solution of SnCl2 (0.1 mol) in 30 mL of concentratedHCl was added dropwise at 0 C. The mixture was stirred at room temperature for 2 h. Afterwards,the mixture was extracted with 50 mL EtOAc and the organic impurities were discarded. Then thesolution was basified with NaOH (40%, aqueous) until it reached pH 7.0. The reaction mass wasextracted with EtOAc three times. Finally, substituted phenylhydrzine 5a-5s was afforded after beingvapored under reduced pressure (in 55%-80% yield) [12].

The synthetic route of 3,5-Dichloroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6775-78-6, 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. 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below.

Step 1: 4-boronobenzoic acid (11.88 g, 71.61 mmol), K3P04 (27.60 g, 13.02 mmol) and Pd(PPh3)4 (3.75 g, 3.25 mmol) were added sequentially to a solution of 6-chloroimidazo[l,2- b]pyridazine (10 g, 65.10 mmol) in a mixture of l,4-dioxane/H20 (250:50 mL) at room temperature under argon atmosphere. The reaction mixture was refluxed for 6 h and was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The combined aqueous layer was acidified to pH 2 using citric acid. The precipitate was isolated by filtration and dried under reduced pressure to afford 4-(imidazo[ 1 ,2-b]pyridazin-6-yl)benzoic acid (4.5 g, 57%) as an off-white solid.1H NMR (400 MHz, DMSO-a?6) delta 13.01 (bs, 1H), 8.04 (s, 1H), 8.3-8.01 (m, 5H), 7.85 (d, J= 7.2 Hz, 2H); MS (ESI) m/z 240 [M+ H]+.

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:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics