Category: 122833-04-9

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

A mixture of starting material (27 mg, 0.1 mmol), 2-methoxy-4-(4-methylpiperazin-1-yl)benzenamine (22 mg, 0.1 mmol), X-Phos (4.3 mg), Pd2(dba)3 (5.5 mg) and K2CO3 (41.5 mg, 0.3 mmol) in t-BuOH (1.5 mL) was heated at 100 C. in a seal tube for 4 h. The reaction was then filtered through celite, eluted with dichloromethane, and concentrated in vacuo. The residue was then purified by reverse-phase prep-HPLC to afford the title compound as the TFA salt (21.5 mg, 47%).

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：
Patent; DANA-FARBER CANCER INSTITUTE, INC.; Gray, Nathanael S.; Waller, David; Choi, Hwan Guen; Wang, Jinhua; Deng, Xianming; (104 pag.)US2016/24115; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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.

Compound 1 A mixture of Intermediate 1 (100 mg, 0.33 mmol), 2-methoxy-4-(4-methylpiperazin-l- yl)aniline (73 mg, 0.33 mmol),, and DIPEA (0.08 ml, 0.49 mmol) in DMSO (5 ml) was stirred at room temperature for 30 min. After checking the TLC, the mixture was added to water (100ml). After cooled with ice-bath, the solids were collected by filtration, washed by water. The crude product was purified by column chromatography (silica gel, 0-15% MeOH in DCM) to give the desired product as yellow solids (64 mg, 40% yield). 1H NMR (400 MHz, DMSO-de) delta 11.34 (br, 1H), 9.45 (br s, 1H), 8.15 (s, 1H), 7.13 (m, 2H), 6.93 (m, 1H), 6.65 (m, 1H), 6.50 (m, 1H), 6.23 (s, 1H), 3.77 (s, 3H), 3.18 (m, 4H), 2.46 (m, 4H), 2.39 (s, 3H), 2.23 (s, 3H); ESI-MS: calcd for C26H26FN702 487, found 488 (MH+). HPLC: retention time: 18.63 min. purity: 96%., 122833-04-9

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

Reference：
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; POLAT,, Tulay; WEINGARTEN, Paul; NALLAN, Laxman; ARP, Forrest; WANG, Qinwei; HO, David; (129 pag.)WO2016/138527; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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

A solution of the product of EXAMPLE 5E (300 mg, 1.4 mmol), 2-methoxy-4-(4- methylpiperazin-l -yl)aniline (338 mg, 1 .53 mmol) and triethylamine (421 mg, 4.1 7 mmol) in 1 ,4-dioxane (30 mL) was stirred at 105C under nitrogen for 12 hours. The solvent was removed under vacuum and the residue was washed with sodium bicarbonate solution and ethanol. The crude product was recrystallized from l ;4-dioxane to give the title compound. ‘ H NMR (DMSO-t?) 6 ppm 12.66 (s, 1H), 1 1.35 (s, 1H), 8.31 (d, 7 = 9.0 Hz, 1H), 8.25 (s, 1H), 6.68 (d, J = 1.2 Hz, 1H), 6.54 (dd, J = 1.2, 9.0 Hz, 1 H), 3.89 (s, 3H), 3.21 -3.10 (m, 4H), 2.50-2.44 (m, 4H), 2.25 (s, 3H)., 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：
Patent; ABBOTT LABORATORIES; VASUDEVAN, Anil; PENNING, Thomas, Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97479; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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.

A solution of the product of EXAMPLE IF (500 mg, 1.40 mmol), 2-methoxy-4-(4- methylpiperazin- 1 -yl)aniline (321 mg, 1.68 mmol) and ^-toluenesulfonic acid (20 mg, cat.) in ?-butanol (10 mL) was heated at 100C 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 x 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+)., 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：
Patent; ABBOTT LABORATORIES; VASUDEVAN, Anil; PENNING, Thomas, Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97479; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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

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

P-toluene sulfonic acid (269 mg, 1.56 mmol) was added to 6-(2-chloro-5-fluoropyrimidin-4-yl)-8-fluoro-2-methyl-3-(prop-1-en-2-yl)imidazo[1,2-a]pyri dine (compound 17, 250 mg, 0.78 mmol) and 2-methoxy-4-(4-methylpiperazin-1-yl)aniline (compound 6, 172 mg, 0.78 mmol) in isopropyl alcohol (10 mL), and reacted under a microwave at 180 C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure, the residue was adjusted to basic with saturated sodium bicarbonate, extracted with dichloromethane (30 mL×3), the organic phase was combined, washed with brine (30 mL) and dried over anhydrous sodium sulfate, the solvent was removed, and the filtrate was separated on column chromatography (eluant:dichloromethane/methanol (v/v)=13:1), to afford 50 mg of a pale yellow solid as a crude, which was purified with preparative TLC (DCM/MeOH v/v=12/1) to afford 32 mg of a pale yellow solid, yield was 8.8%. LC-MS(APCI): m/z=466.5 (M+1); 1H NMR (400 MHz, CDCl3) (delta/ppm) 8.77 (s, 1H), 8.32 (d, J=3.6 Hz, 1H), 8.18 (d, J=8.7 Hz, 1H), 7.75 (d, J=12.1 Hz, 1H), 7.52 (s, 1H), 7.50-7.45 (m, 1H), 6.63-6.58 (m, 1H), 6.58-6.55 (m, 1H), 3.90 (s, 3H), 3.24-3.17 (m, 4H), 2.66-2.59 (m, 4H), 2.50 (s, 3H), 2.37 (s, 3H)., 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：
Patent; Shenzhen TargetRx, Inc.; Wang, Yihan; Ren, Xingye; Jin, Jian; Li, Huanyin; Ai, Yixin; (162 pag.)US2019/152954; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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.

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

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.

To a solution of (R)-2,5- dichloro-N-((tetrahydrofuran-2-yl)methyl)pyrimidin-4-amine (Lawrence, H. R.; et al. (2015) Development of Novel ACK1/TNK2 Inhibitors Using a Fragment Based Approach. /. Med. Chem. 58 (6), 2746-2763) (0.100 g, 0.403 mmol) and 2-methoxy-4-(4-methylpiperazin-l- yl)aniline (98 mg, 0.443 mmol) in 2-methoxyethanol (2 mL) was added 4 M HC1 in dioxane (0.110 mL, 0.443 mmol). The solution was stirred and heated at 110 C for 18 h. Then, the mixture was concentrated under reduced pressure and partitioned between saturated NaHCCb and CHCb (20 mL each). The aqueous layer was re-extracted with CHCb (20 mL). The organic layers were combined, dried (Na2S04), filtered, and concentrated under reduced pressure. The resulting crude mixture was purified by flash chromatography (S1O2) eluting with DCM in MeOH (0% to 10%) to provide the title compound as a brown oil (79 mg, 54%). HPLC: 95% [tR = 6.8 min, 30% MeOH, 70% water (with 0.1% TFA), 20 min. lH NMR (400 MHz, DMSO-ifc): delta 7.84 (s, 1H), 7.78 (d, / = 8.8 Hz, 1H), 7.45 (s, 1H, disappeared on D20 shake), 7.00 (t, / = 6.0 Hz, 1H, disappeared on D20 shake), 6.59 (d, / = 2.6 Hz, 1H), 6.42 (dd, / = 8.8, 2.6 Hz, 1H), 4.03 (pentet, / = 6.0 Hz, 1H), 3.79 (s, 3H), 3.76-3.69 (m, 1H), 3.62-3.56 (m, 1H), 3.36 (t, / = 6.0 Hz, 2H), 3.10-3.04 (m, 4H), 2.46-2.40 (m, 4H), 2.20 (s, 3H), 1.90-1.71 (m, 3H), 1.60-1.50 (m, 1H). HPLC-MS (ESI+): m/z 433.2 [30%, (M35C1+H)+], 218.2 [40%, (M37C1+2H)2+], 217.2 [100%, (M35C1+2H)2+]. LC-MS (ESI+): 433.2 [100%, (M35C1+H)]. HRMS (ESI+): m/z calcd for C21H29CIN6O2 (M+H)+ 433.2113, found 433.2106., 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

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

Ethyl 5-chloro-l ,3,4-thiadiazole-2 -carboxylate (3, 3 g, 15.7 mmol), 2-methoxy-4-(4-methyl piperazin-l -yl)aniline (4, 3.4 g, 15.7 mmol) and p-TSA (3 g, 15.7 mmol) were taken up in IPA (25 mL) and the resultant mixture was stirred at 80 C overnight. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated from the reaction mixture under reduced pressure, and the resultant residue was basified using aq. NaHC03 solution 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 5% MeOH-DCM to afford ethyl 5-((2-methoxy-4-(4-methylpiperazin-l – yl)phenyl)amino)-l ,3,4-thiadiazole-2-carboxylate (5, 1 .5 g, 25%). NMR (400 MHz, CDC13): delta 7.90 (bs, 1 H), 7.43 (d, 1 H), 6.59-6.55 (m, 2H), 4.50 (q, 2H), 3.90 (s, 3H), 3.25-3.22 (m, 4H), 2.65- l .60 (m, 4H), 2.40 (s, 3H), 1.42 (t, 3H)., 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：
Patent; GATEKEEPER PHARMACEUTICAL, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun; WO2011/79231; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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.

?To a solution 6-chiora-M-(3-nitrophenyl)pvrimidin-4-amine (1.0 g, 4.00 minol) in2 -hutanol (10 mL) and trifluoroacetic acid (0.3 mL) was added 2-methoxv-4.4-niethylpiperazin-i-yl)anihne (6o6irig, 4.39 inmol). The reaction mixture was stilTed at 120 C for 10 hrs and the solvent concentrated undcr reduced pressure. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous potassium carbonate solution and brine. The organic layer was dried over Mg504, filtered through a pad of celiteand concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (1:99 to 3:97, ammonia solution 7.0 N in methanol/dichloromethane) to afford N4-(2-methoxy-4-(4-methyipiperazin- 1 -yi)phenyl)-N6- (3-nitrophenyflpyrimidine-4,6-dianiine (1.3 g, 75% yield) as an solid. Rt = 2.73 mm; ?H NMR 600 MHz (DMSO-d6) d 9.50 (s, lH), 8.72 Cc, lH), 8.24 (s, 1H), 8.22 (s, IH), 7.91 (dd, J::: 1.2 Fiz,J 8.4 Hz, iLl), 7.27 (d,J 8.4 Hz, HI), 7.50 (j,J::: 8.4 Hz, iLl), 7.21 (d,J 8.4 Hz, 1H), 6.49 (d,J= 2.4 Hz, 1H). 6.51 (dd,J= 2.4 Hz,J= 9.0 Hz, 1H), 5,76 (s, 1H), 3,77 (s, 3W). 3.16 (in, 4ff). 2,46 (rn, 4ff), 2.32 (s, 3H,); MS mAr: 436.45 [M+i].

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

Reference：
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael; CHOI, Hwan Geun; TAN, Li; WO2015/6492; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics