Downstream synthetic route of 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline

As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Weighing 2-methoxy-4 – (4-methyl piperazin-1-yl) aniline (12C) (2.21g, 10mmol), the 100 ml round-bottom flask. N sequentially adding to the reaction bottle, N-dimethylformamide (20 ml), 2, 4, 5-trichloro-pyrimidine (1.83g, 10mmol) and potassium carbonate (1.79g, 13mmol). The reaction temperature is increased to 80 C stirring 4 hours. After cooling to room temperature to be reacted, the reaction solution is poured into ice water (50 ml), the residue is extracted with methylene chloride (100 ml × 2), the combined organic phase with saturated salt water (50 ml × 2), dried anhydrous sodium sulfate, after concentrating under reduced pressure, the residue is separated by silica gel column chromatography (dichloromethane/methanol (v/v) =15:1) to obtain the title of yellow solid product 2,5-dichloro-N-(2-methoxy-4 – (4-methyl piperazin-1-yl) phenyl) pyrimidin-4-amine (12D) (3.4g, yield: 92.5%), 122833-04-9

As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

Reference:
Patent; Four Chuanhaisike Pharmaceutical Co., Ltd.; Li, Yao; Weiy, Onggang; Zang, Guobiao; Li, Guanpeng; Hu, Shihong; (73 pag.)CN105384694; (2016); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Analyzing the synthesis route of 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline

The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.122833-04-9,2-Methoxy-4-(4-methylpiperazin-1-yl)aniline,as a common compound, the synthetic route is as follows.,122833-04-9

A solution of the product of EXAMPLE 1F (500 mg, 1.40 mmol), 2-methoxy-4-(4-methylpiperazin-1-yl)aniline (321 mg, 1.68 mmol) and p-toluenesulfonic acid (20 mg, cat.) in n-butanol (10 mL) was heated at 100 C. for 18 hours. After cooling, the mixture was poured into saturated aqueous sodium bicarbonate (100 mL) and the solution was extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 20/1 dichloromethane/methanol to afford the title compound. MS: 272.2 (M/2+H+).

The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; Vasudevan, Anil; Penning, Thomas Dale; Chen, Huanming; Liang, Bo; Wang, Shaohui; Zhao, Zhongqiang; Chai, Dikun; Yang, Leifu; Gao, Yingxiang; Pliushchev, Marina; US2014/171429; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

New learning discoveries about 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline

122833-04-9, As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.122833-04-9,2-Methoxy-4-(4-methylpiperazin-1-yl)aniline,as a common compound, the synthetic route is as follows.

General procedure: General procedure for the synthesis of 15b-15u. To a solution ofcompound 13a (0.41 g, 1.06 mmol) in 2-butanol (5 mL), 1-(2-(dimethylamino)ethyl)-1H-pyrazol-4-amine (0.196 g, 1.27 mmol)and trifluoroacetic acid (94 mL) were added in a sealed tube. Thereactionwas heated at 95 C for 18 h. The reaction mixturewas thenallowed to cool to room temperature. The mixture was transferredto a round-bottom flask and then the solvent was removed underreduced pressure. The residue was dissolved in DCM (2.0 mL) andTFA (2.0 mL), and the resulting mixture was stirred for 5 h at roomtemperature. The solvent was removed under reduced pressure,and the residue was neutralized with saturated NaHCO3 aqueoussolution. The water layer was extracted with DCM. The organiclayer was combined and washed with brine, dried over Na2SO4,filtered, concentrated, and purified by silica gel chromatography toafford 15a as a yellow solid (0.264 g, 65% for two steps).

122833-04-9, As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

Reference:
Article; Yu, Lei; Huang, Minhao; Xu, Tianfeng; Tong, Linjiang; Yan, Xiao-e; Zhang, Zhang; Xu, Yong; Yun, Caihong; Xie, Hua; Ding, Ke; Lu, Xiaoyun; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1107 – 1117;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 122833-04-9

122833-04-9, The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Int-12 (100 mg, 0.312 mmol) and 2-methoxy-4-(4-methylpiperazin-l-yl)aniline (75 mg, 0.343 mmol) in 2-methoxyethanol (2 mL) was added 4 M HC1 in dioxane (0.086 mL, 0.343 mmol). The solution was stirred and heated at 110 C for 14 h. Then, additional 2-methoxy-4-(4-methylpiperazin-l-yl)aniline (18 mg, 0.081 mmol) and 1 drop of 4 M HC1 (aq) were added and the mixture was further irradiated under microwave conditions for 15 minutes at 160 C. The solution was concentrated under reduced pressure and partitioned between saturated NaHCC and DCM (20 mL each). The aqueous layer was re-extracted with DCM (20 mL). The organic layers were combined, dried (Na2S04), filtered, and concentrated under reduced pressure. The resulting crude mixture was purified by flash chromatography (Si02) eluting with DCM in MeOH (0% to 10%) to provide the title compound as a brown foam (75 mg, 48%). HPLC: 98% [tR = 8.7 min, 45% MeOH, 55% water (with 0.1% TFA), 20 min. lH NMR (400 MHz, DMSO-ifc): delta 7.87 (d, / = 8.8 Hz, 1H), 7.84 (s, 1H), 7.33-7.22 (m, 4H; 1H disappeared on D20 shake), 7.19-7.11 (m, 1H), 6.60 (d, J = 2.5 Hz, 1H), 6.42 (dd, / = 8.8, 2.5 Hz, 1H), 3.81 (s, 3H), 3.58 (q, / = 6.6 Hz, 2H), 3.10-3.05 (m, 4H), 3.03 (t, J = 6.6 Hz, 2H), 2.46-2.42 (m, 4H), 2.21 (s, 3H). HPLC-MS (ESI+): m/z 507.2 [45%, (M35C137C1+H)+], 505.2 [50%, (M35C135C1+H)+], 254.2 [60%, (M35C137C1+2H)2+], 253.2 [100%, (M35C135C1+2H)2+]. LC-MS (ESI+): 505.2 [100%, (M35C135C1+H)]. HRMS (ESI+): m/z calcd for C24H27C12FN60S (M+H)+ 505.1680, found 505.1683.

122833-04-9, The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE; MAHAJAN, Nupam P.; MAHAJAN, Kiran N.; LAWRENCE, Nicholas J.; LAWRENCE, Hirshani R.; (85 pag.)WO2017/23899; (2017); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 122833-04-9

122833-04-9, As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-Methoxy-4-(4-methylpyridazin-1-yl)phenylamine (2.21 g, 1.0 eq) was added to compound l-1 (3.7 g, 1. Oeq) n-butanol (70 ml) In the solution, the reaction was carried out at 90 C for 2-3 hours. After the reaction was completed by TLC, the mixture was cooled to room temperature, filtered, washed and dried to give a red solid (4.6 g).

122833-04-9, As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

Reference:
Patent; Chengdu University; Zhao Lifeng; Gou Xiaojun; (47 pag.)CN109384788; (2019); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 122833-04-9

The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-methoxy-4-(4-methylpiperazin-l-yl)aniline (331 mg, 1.5 mmol, 1 eq.) and 8-bromo-2-chloroquinazoline (363 mg, 1.5 mmol, 1 eq.) in n-BuOH (10 mL) was added TFA (0.14 mL, 1.8 mmol, 1.2 eq.). The mixture was stirred at 110 C for 12 h. The solution was then cooled to r.t. and concentrated. The resulting residue was dissolved in EA (20 mL), washed with aqueous Na2C03 solution, dried over anhydrous Na2S04and concentrated. The resulting residue was purified via column chromatography (EA/MeOH=5 : 1 , v/v) to afford 8-bromo-N-(2-methoxy-4-(4-methylpiperazin-l-yl)phenyl)quinazolin-2-amine (140 mg, 22% yield)., 122833-04-9

The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUPHARMA, INC.; QIAN, Xiangping; ZHU, Yong-Liang; WO2015/27222; (2015); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of 122833-04-9

122833-04-9 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline 20136253, apiperazines compound, is more and more widely used in various fields.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 4-amino-3-methoxy-N-(3-(4-methylpiperazin-1-yl)propyl)benzamide 20b (52.0 mg, 0.170 mmol) and thieno[3,2-d]pyrimidine-7-carboxylic acid 16 (31.0 mg, 0.170 mmol) in acetonitrile (3.50 mL) was added HATU (129 mg, 0.340 mmol) and DIPEA (59.0 muL, 0.340 mmol) and stirred at 80 C. After confirming the starting material consumption by LC-MS, the reaction mixture was concentrated to give a crude residue. The crude residue was purified by column chromatography utilizing NH silica gel (DCM/methanol) to afford 9b (54.0 mg, 68%) as a yellow solid., 122833-04-9

122833-04-9 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline 20136253, apiperazines compound, is more and more widely used in various fields.

Reference:
Article; Muraoka, Terushige; Ide, Mitsuaki; Morikami, Kenji; Irie, Machiko; Nakamura, Mitsuaki; Miura, Takaaki; Kamikawa, Takayuki; Nishihara, Masamichi; Kashiwagi, Hirotaka; Bioorganic and Medicinal Chemistry; vol. 24; 18; (2016); p. 4206 – 4217;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline

122833-04-9, The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-Chloro-4-(3-nitrophenoxy)quinazoline (3, 500 mg , 1.66 mmol) in isopropanol (IPA) (20 mL) was added p-TSA (315 mg, 1.66 mmol) and compound 4 (367 mg, 1.66 mmol). The solution was then stirred at 100 C for 30 min. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated to dryness, diluted with water, and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resultant crude product was purified by columnchromatography using 2-5% CH3OH-DCM to afford N-(2-methoxy-4-(4-methylpiperazin-l -yl) phenyl)-4-(3-nitrophenoxy) quinazolin-2-amine as yellow solid (5, 0.28 g, 34.6 %). NMR (CDClj): delta 8.30-8.10 (m, 3H), 7.80-7.60 (m, 4H), 7.40-7.20 (m, 2H), 6.50 (s, 1 H), 6.40 (bs, 1 H), 3.80 (s, 3H), 3.20-3.00 (m, 4H), 2.70-2.60 (m, 4H), 2.40 (s, 3H).

122833-04-9, The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GATEKEEPER PHARMACEUTICAL, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun; WO2011/79231; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline

122833-04-9, The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-Chloro-4-(3-nitrophenoxy)quinazoline (3, 500 mg , 1.66 mmol) in isopropanol (IPA) (20 mL) was added p-TSA (315 mg, 1.66 mmol) and compound 4 (367 mg, 1.66 mmol). The solution was then stirred at 100 C for 30 min. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated to dryness, diluted with water, and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resultant crude product was purified by columnchromatography using 2-5% CH3OH-DCM to afford N-(2-methoxy-4-(4-methylpiperazin-l -yl) phenyl)-4-(3-nitrophenoxy) quinazolin-2-amine as yellow solid (5, 0.28 g, 34.6 %). NMR (CDClj): delta 8.30-8.10 (m, 3H), 7.80-7.60 (m, 4H), 7.40-7.20 (m, 2H), 6.50 (s, 1 H), 6.40 (bs, 1 H), 3.80 (s, 3H), 3.20-3.00 (m, 4H), 2.70-2.60 (m, 4H), 2.40 (s, 3H).

122833-04-9, The synthetic route of 122833-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GATEKEEPER PHARMACEUTICAL, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun; WO2011/79231; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of 122833-04-9

122833-04-9 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline 20136253, apiperazines compound, is more and more widely used in various fields.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 4-amino-3-methoxy-N-(3-(4-methylpiperazin-1-yl)propyl)benzamide 20b (52.0 mg, 0.170 mmol) and thieno[3,2-d]pyrimidine-7-carboxylic acid 16 (31.0 mg, 0.170 mmol) in acetonitrile (3.50 mL) was added HATU (129 mg, 0.340 mmol) and DIPEA (59.0 muL, 0.340 mmol) and stirred at 80 C. After confirming the starting material consumption by LC-MS, the reaction mixture was concentrated to give a crude residue. The crude residue was purified by column chromatography utilizing NH silica gel (DCM/methanol) to afford 9b (54.0 mg, 68%) as a yellow solid., 122833-04-9

122833-04-9 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline 20136253, apiperazines compound, is more and more widely used in various fields.

Reference:
Article; Muraoka, Terushige; Ide, Mitsuaki; Morikami, Kenji; Irie, Machiko; Nakamura, Mitsuaki; Miura, Takaaki; Kamikawa, Takayuki; Nishihara, Masamichi; Kashiwagi, Hirotaka; Bioorganic and Medicinal Chemistry; vol. 24; 18; (2016); p. 4206 – 4217;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics