Chlorides-buliding-blocks

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

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

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

83121-15-7, Name is 3,5-Dichloro-2,4-difluoroaniline, 83121-15-7, 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.

Example 10 N-(2,4-Difluoro-3,5-dichlorophenyl)-N’-(2,6-difluorobenzoyl)-urea Three grams (0.016 mol) of 2,6-difluoro-benzoyl isocyanate were added to a solution of 2.95 gm (0.015 mol) of 2,4-difluoro-3,5-dichloroaniline in 50 ml of toluene. The solution thus obtained was stirred for 15 hours at room temperature. Thereafter, the product which precipitated during that time was removed by suction filtration and dried. Yield: 4.2 gm (0.011 mol; 73% of theory), M.p.: 221-224 C.

Statistics shows that 3,5-Dichloro-2,4-difluoroaniline is playing an increasingly important role. we look forward to future research findings about 83121-15-7.

Reference:
Patent; Celamerck GmbH & Co. KG; US4457943; (1984); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, The chemical industry reduces the impact on the environment during synthesis 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life.

A mixture of 8-bromo-6-chloroimidazo[l,2-b]pyridazine (2 g, 8.6 mmol) and 5,6- dimethoxypyridin-2-amine (1.39 g, 9.03 mmol) in DMF (72 ml) was cooled to 0 C. To the mixture was added sodium hydride (1.1 g, 27.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 10 min then warmed to room temperature. After 15 h the reaction was quenched with saturated sodium bicarbonate solution, and then diluted with water and EtOAc. An insoluble solid was filtered off. The filtrate was separated and the aqueous phase was washed with EtOAc. The combined organic extracts were concentrated in vacuo and the residue obtained was crystalized from methanol to give 6-chloro-N-(5,6-dimethoxypyridin -2- yl)imidazo[l,2-b]pyridazin-8-amine (2.4 g, 7.85 mmo 1, 91.2 %) as light brown needles. 1H NMR (300 MHz, CHLOROFORM- ) delta ppm 8.26 (br. s., 1 H) 7.95 (s, 1 H) 7.81 (s, 1 H) 7.55 (s, 1 H) 7.15 (d, J=7.93 Hz, 1 H) 6.58 (d, J=8.31 Hz, 1 H) 4.12 (s, 3 H) 3.89 (s, 3 H); LC/MS: 305.9 [MH]+.

The chemical industry reduces the impact on the environment during synthesis 8-Bromo-6-chloroimidazo[1,2-b]pyridazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 1871-57-4 as follows. 1871-57-4

To sodium hydride (60 wt.% in mineral oil, 2.464 g, 61.6 mmol) in DMF (50 mL) was added 3-chloro-2-(chloromethyl)prop-l-ene (3.5 g, 28.0 mmol) at ~5 C (ice bath) and a solution of tert-butyl(2-hydroxyethyl)carbamate (4.51 g, 28.0 mmol) in tetrahydrofuran (50 mL). The reaction mixture was stirred at 20-30 C for ~2 hrs and concentrated under reduced pressure to remove tetrahydrofuran. The resulting mixture was poured into water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 80 g, EtO Ac/heptane = 0/100 to 50/50] providing tert-butyl 6-methylene-l ,4-oxazepane-4- carboxylate (4 g) as a colorless oil. NMR (400 MHz, chloroform-d) delta [ppm]: 1.46 (s, 9 H) 3.33 – 3.62 (m, 2 H) 3.62 – 3.82 (m, 2 H) 4.09 (m, 2 H) 4.16 (m, 2 H) 4.99 (m,2 H).

According to the analysis of related databases, 1871-57-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6579-54-0, 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. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, 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 mixture of 2,4-dichloro-5-methylpyrimidine (4.17g, 25.6mmol) and 4-acetamidophenylboronic acid (5.Og, 27.9mmol) in DME (40ml) was added Et3N (8.92ml, 64.0mmol), H2O (4ml), and dichloro[l,r-bis(diphenylphosphino)ferrocenepalladium (2.8 Ig, 3.44mmol, 13%). The mixture was allowed to stir at reflux for 5hrs. After the mixture was cooled down to rt, the crude mixture was directly filtered on silica gel and eluted with EtOAc. The filtrate was concentrated in vacuo. Further purification was conducted by flash chromatography to afford Intermediate 1 (5.94g, 89%) as a white solid. LCMS: m/z 262 (M+H)+.[0246] To a stirred solution of chloropyrimidine (1.05g, 4.0mmol) in 1-butanol (10ml) was added N-Boc-amino-3-aniline (920mg, 4.4mmol) and the mixture was heated in the sealed tube at 18O0C for 1.5hr. The mixture was cooled down to rt and acidified with IN HCl (20ml). The aqueous layer was washed with EtOAc (50ml). The separated aqueous layer was basified with 2N NaOH to pH 8-9 and extracted with EtOAc (50ml*3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by flash 5 chromatography to afford product Intermediate K (943mg, 71% as a light yellow solid. LCMS: m/z 334 (M+H)+.[02471 To a stirred suspension of aniline (250mg, 0.75mmol) in THF (5ml) was added DIPEA (157ml, 0.90mmol) and 2,6-dichlorobenzenesulfonyl chloride (203 mg, 0.83mmol) and the mixture containing intermediate K was stirred at reflux for 2hrs. After cooling down to rt, the mixture was diluted with EtOAc, washed with H?O, brine, and dried over Na2SO4. After concentrated in vacuo, the residue was purified by flash chromatography to give product 26 (299mg, 73%) as a light pink solid.1H-NMR (400MHz, d6-DMSO): 10.71 (s, IH), 10.16 (s, IH), 9.54 (s, IH), 8.34 (s, IH), 7.75- 7.69 (m, 5H), 7.60 (dd, 2H), 7.51 (dd, IH), 7.31 (dd, IH), 7.09 (t, IH), 6.66 (dd, IH), 2.25 (s, 3H), 2.08 (s, 3H); MS (EI) C25H2ICl2N5O3S: 542.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; WO2007/89768; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

26487-67-2, 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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,1-bis(4-hydroxyphenyl)-2-cyclohexyl-2-phenylethene (37.6 mg, 0.101 mmol) in DMF (1.02 mL) at 0 ¡ãC was added 60percent sodium hydride (dispersion in paraffin liquid, 24.4 mg, 0.610 mmol). The reaction mixture was stirred for 15 min at 50 ¡ãC and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (66.4 mg, 0.335 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 15.5 h at 50 ¡ãC, saturated aqueous ammonium chloride was added at 0 ¡ãC. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 9/1) to afford RID-F-S*13 (compound 9) (51.9 mg, 83percent) as a pale yellow oil

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

348-59-4, 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 348-59-4 as follows.

Step 1 a) The mixture of 1 ,4-dichloro-2-fluoro-benzene (5.4 g, 0.0327 mol), AICI3 (10.4 g, 0.0784 mol) was warmed to 60 C, and acetyl chloride (3.85 g, 0.0491 mol) was added by syringe over 5 min under N2, the mixture was warmed to 100 C for 2h. Then the mixture was added into ice water and adjusted pH to 2 by 1 N HCI. Extracted by MTBE (100 ml*2), dried and concentrated to give 1 – (2,5-dichloro-4-fluoro-phenyl)ethanone (6g, crude). 1H NMR : CDCI3 400MHz, delta (ppm)= 2.58 (s, 3 H), 7.19 (d, J=8.38 Hz, 1 H), 7.63 (d, J=7.94 Hz, 1 H).

According to the analysis of related databases, 2,5-Dichlorofluorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MUeLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; GROTE, Thomas; HADEN, Egon; ESCRIBANO CUESTA, Ana; WO2014/82879; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

627-42-9, Adding some certain compound to certain chemical reactions, such as: 627-42-9, name is 2-Methoxyethyl chloride, 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 627-42-9.

Adding 76.1 g (0.5 mol) of methyl salicylate to 250 ml of N-methylpyrrolidone,2-chloromethyl ethyl ether 56.7 g (0.6 mol),Potassium iodide 8.3g (0.05mol),Potassium carbonate 82.9g (0.6mol),It was stirred at 120 C for 16 hours.After cooling the reaction solution, 300 ml of water was added,Extracted with 300 ml of ethyl acetate,After washing the ethyl acetate solution with saturated brine,The solvent was distilled off. Thereafter, 40 g of a 50% aqueous NaOH solution, 40 ml of water, and 40 ml of ethanol were added.It was stirred at 100 C for 1 hour.After the reaction is completed, hydrochloric acid water is added for neutralization.Ethyl acetate was added for extraction.The ethyl acetate solution is washed with saturated brine.The solvent was distilled off. Thereafter,Purification by ruthenium column chromatographyAnd get 59g(yield 60%)Intermediate 4.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 627-42-9.

Reference:
Patent; Fujifilm Corporation; Takasaki, Yuta; Sasaki, Daisuke; Ishizaka, Soji; (141 pag.)TWI626233; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics