Category: 13726-14-2

Application of 13726-14-2, 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure B: 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.

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, 4-Chloro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, These common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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.

Ir (ppy) 3 (2 mg) and DMF (1 ml) were added to the reaction flask under nitrogen or argon atmosphere and then irradiated with a blue LED band (7 W) at room temperature until complete conversion of the trivalent iodine reagent was completed. 10 ml of a saturated aqueous Na2C03 solution was added thereto, and the mixture was extracted three times with ethyl acetate. The organic layer was washed once with saturated brine, and the organic layer was dried over anhydrous Na2S04. Column chromatography (eluent: petroleum ether 60-90: ethyl acetate = 20: 1-10: 1) afforded the product in a yield of 62%

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University; Zhu, ChengJian; Xie, jin; Xu, Pan; (13 pag.)CN103553857; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13726-14-2, name is 4-Chloro-3-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 13726-14-2, Recommanded Product: 4-Chloro-3-methoxyaniline

5-NITRO-2-CHLORO aniline (50.0 g, 0.289 mol) in 30 % sulfuric acid (300 ml) was stirred at RT FOR 2 h. Sodium nitrite (21.0 g, 0.304 mol) in water (50 ml) was added slowly at 0C and maintained at this temperature for 15 min. This diazotized solution was added slowly to dilute sulfuric acid (50 %, 250 ML) at 110 C. Stirring was continued for 15 min. After cooling to RT, ice water was added, the mixture extracted with ethylacetate, washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield 12.0 g, 24. 0 %. [00162] To K2CO3 (23.84 g, 0.172 mol) and 2-chloro-5-nitrophenol (10.0 g, 0.0576 mol) in ACETONITRILE (100 ml) was added methyl iodide (19.60 g, 0.138 mol) at 0C. The reaction mixture was warmed to RT and stirred overnight. Water was added and extracted with ethyl acetate. The organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield : 6.0 g, 55. 55 %. [00163] 2-CHLORO-5-NITRO ANISOLE (6.0 g, 0.032 mol) in MEOH (45 ml) was added slowly to stannous chloride (15.1 g, 0.08 mol) in conc. HCI (110 ml) at 40 C and the temperature was slowly raised to 50 C. Stirring was continued for 2h, the reaction cooled to RT, basified with 50 % NAOH solution and extracted by ethyl acetate. The organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield : 4.0 g, 79.36 %. [00164] To triethylamine (3.83 g, 0.037 mol) and 3-methoxy-4- chloro aniline (3.0 g, 0.0190 mol) in benzene (50 ML) was added trimethylacetylchloride (2.75 g, 0.022 mol) slowly at 0 C. The temperature was raised to RT and stirred overnight. The reaction mixture was added to ice and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over NA2SO4 and concentrated. Yield : 3.7 g, 80.43 %. [00165] To N-PIVALOYL-3-METHOXY-4-CHLOROANILINE (1.50 g, 0.0062 mol) in THF (30 ML) was added n-butyl lithium (1.0 g, 0.0156 mol) at 0 C and the reaction stirred for 2 hr. After cooling to-70 C, methyl isonicotinate (1.3 g, 0.0094 mol) in THF (12 ml) was added slowly. The reaction was warmed to rt and stirred overnight and then quenched with water and extracted with ether. The water layer was further extracted and the combined ether layers were washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield 0.50 g, 23. 25 %. [00166] The protected ketone from step 5 (0.500g, 0. 0014MOL) was suspended in concentrated HCI (5 ml) at RT, then the temperature was raised to 95 C and the mixture stirred over night. The mixture was cooled to RT, basified with 20 % NAOH solution and extracted with DCM. The combined organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography using basic alumina to yield title compound (0.140 g, 37.33%).

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, 4-Chloro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHEMOCENTRYX; WO2004/46092; (2004); A2;,
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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., SDS of cas: 13726-14-2

Step 1 :Exp-4-g1Step 1 : preparation of 2-Chloro-N-(4-chloro-3-methoxyphenyl)pyridine-3- carboxamide (Exp-4-g3)[0100] Into a vessel containing a solution prepared by dissolving 1 g of 2- chloropyridine-3-carboxylic acid (Exp-4-gl, 6.37 mmol) and 1 g of 4-chloro-3- methoxy-phenylamine (Exp-4-g2, 6.4 mmol) in 30 mL of DMF was added 6.05 g 0- 7- Azabenzotriazol-l-yl)-N,N,N’N’-tetramethyluronium hexafluorophosphate (HATU, 15.9 mmol), and 1.93 g triethylamine (TEA, 19.1 mmol). The reaction mixture thus provided was stirred at ambient temperature (RT) overnight then the mixture was poured into cool water and the resulting mixture extracted with sufficient amounts of EtOAc to obtain the product from the reaction mixture. The organics were combined, washed with brine, dried over MgSC>4, filtered and concentrated under reduced pressure. The residue thus provided was purified on silica column chromatogram (PE:EtOAc = 50: 1-1 : 1) to give 1.1 g of Exp-4-g3 (calculated yield 58%).

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP; ADDEX PHARMA S.A.; LIVERTON, Nigel; JONES, Philip; BOLEA, Christelle; CELANIRE, Sylvain; TANG, Lam; BOUDOU, Cedric; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/60029; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13726-14-2, name is 4-Chloro-3-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 13726-14-2, Recommanded Product: 13726-14-2

A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). NMR (400 MHz, DMSO-ifc) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, / = 2.3 Hz, 1H), 7.43 (d, / = 8.6 Hz, 1H), 7.28 (dd, / = 8.6, 2.3 Hz, 1H), 4.37 (q, / = 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, / = 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

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; 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

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 13726-14-2 as follows. Product Details of 13726-14-2

To a solution of 4-chloro-3-methoxyaniline (50 g, 3 i 7 mmol) and DIPEA (i iO mE, 635 mmol) in CH2C12 (700 mE) was added acetic anhydride (36 mE, 38i mmol) drop wise at 00 C. and the reaction mixture was stirred at room temperature for 3 h. The reaction then was quenched with water (250 mE) and the organic layer was separated. The aqueous layer was extracted with CH2C12 (iOO mEx3). The combined organic layers were dried (Na2504), concentrated and purified by flash chromatography with CH2C12/MeOH to give N-(4-chloro-3-methoxy phenyl)acetamide (7i g, quantitative yield) as a white solid.

According to the analysis of related databases, 13726-14-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Forma Therapeutics, Inc.; Lin, Jian; Ericsson, Anna; Campbell, Ann-Marie; Gustafson, Gary; Wang, Zhongguo; Diebold, R. Bruce; Ashwell, Susan; Lancia, Jr., David R.; Caravella, Justin Andrew; Lu, Wei; (57 pag.)US2016/311818; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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 13726-14-2. 13726-14-2

Ethyl 2-chloro-4-(4-chloro-3-methoxyphenylamino)pyrimidine-5-carboxylate (RJ1- 061): A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). XH NMR (400 MHz, DMSO-) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, J= 2.3 Hz, 1H), 7.43 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 8.6, 2.3 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, J= 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

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 4-Chloro-3-methoxyaniline.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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. 13726-14-2

Into a vessel containing 3 mL of dioxane was added 60 mg of Exp-5-g24 prepared in Step 2 (0.19 mmol), 31 mg of 4-chloro-3-methoxy-phenylamine (0.2 mmol), 18 mg of Pd2dba3 (0.02 mmol), 23 mg of Xantphos (0.04 mmol) and 130 mg Cs2C03 (0.4 mmol). The reaction mixture thus provided was maintained under an 2 atmosphere, refluxed for 3 hours, then cooled to ambient temperature, filtered and concentrated under reduced pressure. The residue thus provided was purified by Prep-TLC (PE:EtOAc = 1 :2) yielding 65 mg of Exp-5-g25 (calculated yield 70 %).

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, 13726-14-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; JONES, Philip; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/63100; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13726-14-2, name is 4-Chloro-3-methoxyaniline, I believe this compound will play a more active role in future production and life. 13726-14-2

This was prepared from 2,4-dichloro-5-iodopyrimdine(0.550 g) and 3-methoxy-4-chloroaniline (0.315 g) using procedure B (reaction time, 1 h) to give the title compound as a gray solid (0.708 g, 90%). Mp: 190-192 C (dec). lH NMR (400 MHz, DMSO-ifc): delta 8.94 (s, 1H, disappeared on D20 shake ), 8.59 (s, 1H), 7.43 (d, / = 2.3 Hz, 1H), 7.41 (d, / = 8.6 Hz, 1H), 7.21 (dd, / = 8.6, 2.3 Hz, 1H), 3.84 (s, 3H). HPLC-MS (ESI+): m/z 397.9 [78%, (M35C137C1+H)+], 395.9 [100%, (M35C135C1+H)+].

The chemical industry reduces the impact on the environment during synthesis 13726-14-2. I believe this compound will play a more active role in future production and life.

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

13726-14-2, 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 13726-14-2 as follows.

General procedure: Procedure B: 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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 13726-14-2, and friends who are interested can also refer to it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics