Category: 13726-14-2

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., category: chlorides-buliding-blocks

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. 2,5-Dichloro-/Y4-(4-chloro-3-methoxyphenyl)pyrimidin-4-amine (SG1-168): This was prepared from 2,4,5-trichloropyrimidine (0.500 g), 4-chloro-3-methoxyaniline (0.451 g), and DIPEA (0.570 mL) using procedure B (reaction time, 12 h). The solvent was removed and EtOAc (20 mL) was added. The organic layer was extracted with water (20 mL). The aqueous layer was re-extracted with EtOAc (20 mL). The organic layers were combined and washed with water and brine (20 mL each), dried (Na2S04) and concentrated under reduced pressure. The resulting dark purple oil was triturated using EtOAc/hexanes to give the title compound as a light purple solid (0.680 g, 82%). Mp: 136-138 C. NMR (400 MHz, DMSO-ifc): delta 9.57 (s, 1H, disappeared on D20 shake), 8.41 (s, 1H), 7.49 (d, / = 2.2 Hz, 1H), 7.41 (d, / = 8.6 Hz, 1H), 7.28 (dd, / = 8.6, 2.2 Hz, 1H), 3.82 (s, 3H). HPLC-MS (ESI+): m/z 308.1 [40%, (M35C137C137C1+H)+], 306.1 [98%, (M35C135C137C1+H)+], 304.0 [100%, (M35C135C135C1+H)+].

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

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

Application of 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.

This was prepared from MA1-012 (0.531 g) and 3-methoxy-4-chloroaniline (0.473 g) using procedure A (reaction time, 16 h) to give the title compound as a white solid (0.202 g, 23%). Mp: 143-144 C. lH NMR (400 MHz, DMSO-ifc): delta 8.93 (s, IH, disappeared on D20 shake), 8.07 (s, IH), 7.53 (d, / = 2.3 Hz, IH), 7.37 (d, / = 8.6 Hz, IH), 7.31 (dd, / = 8.6, 2.3 Hz, IH), 3.83 (s, 3H), 2.61 (q, J = 7.4 Hz, 2H), 1.17 (t, / = 7.4 Hz, 3H). HPLC-MS (ESI+): m/z 300.1 [70%, (M37C135C1+H)+], m/z 298.1 [100%, (M35C135C1+H)+]. Further elution gave the bis- adddition side product MA1-025B (109 mg, 9%) as a yellow solid, Mp: 201 C (dec). HPLC: 99% [tR = 8.1 min, 65% MeOH, 35% water (with 0.1% TFA), 20 min]. lH NMR (400 MHz, DMSO-ifc): delta 9.20 (s, IH, disappeared on D20 shake), 8.48 (s, IH, 40% reduced on D20 shake), 7.97 (s, IH), 7.56 (d, / = 2.3 Hz, IH), 7.43 (d, / = 2.3 Hz, IH), 7.38 (dd, / = 8.6, 2.3 Hz, IH), 7.32 (d, / = 8.7 Hz, IH) 7.29 (dd, / = 8.6, 2.3 Hz, IH), 7.15 (d, / = 8.7 Hz, IH), 3.74 (s, 3H), 3.60 (s, 3H), 2.57 (q, / = 7.4 Hz, 2H), 1.18 (t, / = 7.4 Hz, 3H). HPLC-MS (ESI+): m/z 421.1 [70%, (M37C135C1+H)+], 419.2 [100%, (M35C135C1+H)+]. LC-MS (ESI+): 421.1 [70%, (M37C135C1+H)+], 419.1 [100%, (M35C135C1+H)+]. HRMS (ESI+): m/z calcd for C20H20CI2N4O2 (M+H)+ 1035.Pr ocedure A: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.) and substituted aniline (1.15 equiv.) in MeOH/water (1 : 1.5, 0.2 M) was stirred at 45 C. The reaction time is indicated below. Upon cooling to ambient temperature, the desired product precipitated and was filtered, washed with MeOH/water (1 : 1.5, 20 mL), and dried. 2,5-Dichloro-/Y4-(4-[/Y-(l,l-dimethylethyl)sulfamoyl]phenyl)pyrimidin-4-amine (SG1-182): This was prepared from 2,4,5-trichloropyrimidine (0.500 g) and SG1-177 (0.715 g) using procedure A (stirred for 4 d). The crude solid was purified via flash chromatography (S1O2) eluting with hexanes/EtOAc (0: 10 to 4:6 v/v) to provide the title compound as a tangerine-colored solid (0.590 g, 58%). Mp: 180-181 C. NMR (400 MHz, DMSO-ifc): delta 9.73 (s, IH, disappeared on D20 shake), 8.46 (s, IH), 7.80 (s, 4H), 7.48 (s, IH, disappeared on D20 shake), 1.09 (s, 9H). HPLC-MS (ESI+): m/z 773.1 [10%, (MCl35Cl37+M35Cl35Cl+Na)+], 379.1 [10%, (MC137C137+H)+], 377.1 [70%, (MC135C137+H)+], 375.1 [100%, (M35C135C1+H)+].

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; 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

Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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. Product Details of 13726-14-2

Benzoyl isothiocyanate (8.8 mL, 64 mmol) was added dropwise to a solution of 4-chloro- 3-methoxy-benzenamine (10 g, 63 mmol) in 160 mL THF. The mixture was stirred at room temperature for 40 minutes, volatiles were removed and the residue was dissolved in 400 mL methanol. A solution of potassium carbonate (26.3 g, 190 mmol) in 200 mL water was added and the mixture was stirred at room temperature for 90 minutes. The title product (13.5 g, 98%) precipitated after removal of 450 mL of the solvents. MS (m/e): 216.0, 218.0 (M+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13726-14-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/58887; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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.

Step-1: N-(4-chloro-3-methoxyphenyl)acetamide [0112] To a solution of 4-chloro-3-methoxyaniline (50 g, 317 mmol) and DIPEA (110 mL, 635 mmol) in CH2Cl2 (700 mL) was added acetic anhydride (36 mL, 381 mmol) drop wise at 0 C and the reaction mixture was stirred at room temperature for 3 h. The reaction then was quenched with water (250 mL) and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (100 mL x 3). The combined organic layers were dried (Na2SO4), concentrated and purified by flash chromatography with CH2Cl2/MeOH to give N- (4-chloro-3-methoxy phenyl)acetamide (71 g, quantitative yield) as a white solid.

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; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (147 pag.)WO2016/171755; (2016); 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. HPLC of Formula: C7H8ClNO

General procedure: Procedure A: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.) and substituted aniline (1.15 equiv.) in MeOH/water (1 : 1.5, 0.2 M) was stirred at 45 C. The reaction time is indicated below. Upon cooling to ambient temperature, the desired product precipitated and was filtered, washed with MeOH/water (1 : 1.5, 20 mL), and dried.

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

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

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. COA of Formula: C7H8ClNO

General procedure: To a solution containing para-chloro-meta-fluoroaniline (10.0 g, 70.1 mmol) in 600 mL THF at 0 C was added Et3N (9.11 mL, 70.1 mmol) followed by ethyl oxalylchloride (7.70 mL, 70.1 mmol) dropwise over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 18 hrs. The reaction mixture was filtered and the filter cake was washed with one-300 mL portion of ethyl acetate. The organic phase was washed with two-100 mL portions of 1M HCl, dried over MgSO4, filtered, and concentrated to give the product. Recrystallization from hot Et2O gave 14.4 g (84%) of 27 as a colorless crystalline solid.

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

Reference:
Article; Lalonde, Judith M.; Elban, Mark A.; Courter, Joel R.; Sugawara, Akihiro; Soeta, Takahiro; Madani, Navid; Princiotto, Amy M.; Kwon, Young Do; Kwong, Peter D.; Schoen, Arne; Freire, Ernesto; Sodroski, Joseph; Smith III, Amos B.; Bioorganic and Medicinal Chemistry; vol. 19; 1; (2011); p. 91 – 101;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, A common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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.

To a solution of compound 5 (15 mg, 0.037 mmol) in DMF (3 mL)4-Chloro-3-methoxyaniline (6.2 mg, 0.04 mmol) was added.HATU (17 mg, 0.045 mmol) and TEA (7.5 mg, 0.074 mmol),Stir at room temperature for 2 hours,It was poured into water (10 mL) and extracted with ethyl acetate (2×5 mL).The organic phase was separated and washed with saturated aqueous NaCI (2×).The organic phase was separated and dried over anhydrous Na2SO4, filtered and concentrated.The residue was purified by silica gel column chromatography.Elution with ethyl acetate/petroleum ether (1:2) gave the desired compound I-8 (11 mg, 55%).

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

Reference:
Patent; Nanjing Gentai Pharmaceutical Co., Ltd.; Chen Rongyao; Shen Yu; (48 pag.)CN110218182; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route 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.

3 was synthesized in a similar procedure as described for 2 by using 4-chloro-3-methoxyaniline (400 mg, 2.54 mmol), 1 (312 mg, 2.54 mmol), HOBt·H2O (389 mg, 2.54 mmol), DIPEA (0.66 g, 5.08 mmol), EDC.HCl (730 mg, 3.81 mmol) and anhydrous 1,4-dioxane (30 mL). 3 was obtained as a pale yellow solid (325 mg, 1.34 mmol, 53 % yield); mp: 120 C. 1H NMR (500MHz, CDCl3) delta ppm 10.07 (s, 1H), 8.63 (d, J=4.0Hz, 1H), 8.29 (d, J=8.0Hz, 1H), 7.92 (ddd, J=7.6, 7.6, 1.6Hz, 1H), 7.81 (d, J=2.0Hz, 1H), 7.50 (dd, J=7.0Hz, 5.0Hz, 1H), 7.34 (d, J=8.5Hz, 1H), 7.09 (dd, J=9, 2.5Hz, 1H), 3.97 (s, 3H). 13C NMR (125MHz, CDCl3) delta ppm 162.41, 155.68, 149.85, 148.37, 138.17, 137.97, 130.47, 127.01, 122.72, 117.80, 112.45, 104.37. LC-MS, calcd for C13H11N2O2Cl: 262.05; obsd: 263.0 [M+H]+.

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

Reference:
Article; Kil, Kun-Eek; Zhang, Zhaoda; Jokivarsi, Kimmo; Gong, Chunyu; Choi, Ji-Kyung; Kura, Sreekanth; Brownell, Anna-Liisa; Bioorganic and Medicinal Chemistry; vol. 21; 19; (2013); p. 5955 – 5962;,
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., category: chlorides-buliding-blocks

To a solution of 2-t-butoxycarbonylaminobenzoic acid (115 mg, 0.485 mmol) in DMF (2.0 mL) was added a solution of 4-chloro-3-methoxyaniline (82.2 mg, 0.522 mmol), HOBt (70.0 mg, 0.518 mmol), EDCI·HCl (104 mg, 0.542 mmol) and DIEA (90.0 muL, 0.522 mmol) in DMF (1.0 mL). The resulting mixture was stirred at r.t. overnight. After completion of the reaction, AcOEt was added. The organic layer was washed with water and brine, dried, and concentrated to give the title compound as a pale yellow paste, which was used for the next step without further purification.

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:
Article; Numadate, Akiyoshi; Mita, Yusuke; Matsumoto, Yotaro; Fujii, Shinya; Hashimoto, Yuichi; Chemical and Pharmaceutical Bulletin; vol. 62; 10; (2014); p. 979 – 988;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13726-14-2, 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.

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