Category: 163765-44-4

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.163765-44-4,(R)-1-Boc-3-Methylpiperazine,as a common compound, the synthetic route is as follows.

(R)-Terf-butyl 3-methylpiperazine-1 -carboxylate (1 .77 g, 8.82 mmol) and glacial acetic acid (530 mg, 505 muIota_, 8.82 mmol) were added to a stirred solution of 7-bromo-5-methyl-4-oxo-4,5- dihydrothieno[3,2-c]pyridine-2-carbaldehyde (for a preparation see Intermediate 3, 2.0 g, 7.35 mmol) in dichloromethane (50 ml_). The reaction mixture was stirred at room temperature for 30 minutes then treated with sodium triacetoxyborohydride (7.79 g, 36.7 mmol). The reaction mixture was stirred at room temperature for 8 hours then allowed to stand overnight. Saturated sodium bicarbonate solution (75 ml.) was added and the mixture stirred for 10 minutes. The organic phase was separated and the aqueous phase extracted with dichloromethane (2 x 50 ml_). The combined organics were dried and evaporated. The residue was purified by chromatography on silica gel eluting with 3% methanol in dichloromethane, followed by trituration with diethyl ether gave (R)-tert- butyl 4-((7-bromo-5-methyl-4-oxo-4,5-dihydrothieno[3,2-c]pyridin-2-yl)methyl)-3-methylpiperazine-1 – carboxylate (3.1 g, 6.79 mmol, 92% yield) as a yellow solid. LCMS (2 min, Formic Acid): Rt = 0.77 min, MH+ = 456/458.

163765-44-4, The synthetic route of 163765-44-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; BAMBOROUGH, Paul; BIT, Rino, Antonio; BROWN, John, Alexander; CAMPBELL, Matthew; LINDON, Matthew, John; SHIPLEY, Tracy, Jane; THEODOULOU, Natalie, Hope; WELLAWAY, Christopher, Roland; WESTAWAY, Susan, Marie; WO2014/78257; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

163765-44-4, (R)-1-Boc-3-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-Bromo-2-chloropyrimidine (7.50 g, 38.77 mmol), (3R)-1-Boc-3-methylpiperazine (8.15 g, 40.71 mmol) and potassium carbonate (6.08 mL, 100.81 mmol) were suspended in butyronitrile (90 mL) and heated to 120 C. for 15 hours and cooled to RT. The solvent was removed in vacuo and the residue taken up in ethyl acetate (500 mL), washed with water (70 mL) and brine (70 mL), dried (sodium sulphate), filtered and evaporated to leave the crude product. The crude product was purified by flash silica chromatography elution gradient 0 to 20% EtOAc in DCM. Pure fractions were evaporated to dryness to afford (R)-tert-butyl 4-(5-bromopyrimidin-2-yl)-3-methylpiperazine-1-carboxylate (13.69 g, 99%) as a pale yellow gum which crystallised on standing. 1H NMR (400 MHz, DMSO) 1.05 (d, 3H), 1.4 (s, 9H), 2.9 (m, 1H), 3.1 (m, 2H), 3.8 (d, 1H), 3.95 (m, 1H), 4.3 (d, 1H), 4.7 (m, 1H), 8.45 (s, 2H). m/z (ES+) (M+H)+=358; HPLC tR=3.55 min., 163765-44-4

The synthetic route of 163765-44-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AstraZeneca AB; US2011/65706; (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.163765-44-4,(R)-1-Boc-3-Methylpiperazine,as a common compound, the synthetic route is as follows.

(c) (R)-4-[5-(4-Bromo-2-chloro-5-trifluoromethoxy-phenylcarbamoyl)-pyridin-2-yl]-3-methyl-piperazine-1-carboxylic acid tert-butyl ester To a reaction mixture of the product of the previous step (999 mg, 2.42 mmol) in a mixture of N,N-diisopropylethylamine (0.84 mL, 4.83 mmol;) and DMSO (0.86 mL, 12.08 mmol) was added (R)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (726 mg, 3.62 mmol) and the reaction mixture was heated at 120 C. overnight and extracted with ethyl acetate/water. The organic layer was dried over sodium sulfate and concentrated under vacuum. The dark oil was dissolved in a small amount of DCM and purified by silica gel chromatography (24 g column, 0-40% ethyl acetate:hexanes) to produce the title intermediate as a white solid (916 mg, 64% yield). (m/z): [M+H]+ calcd for C23H25BrClF3N4O4 593.07; 595.07. found 595.4., 163765-44-4

163765-44-4 (R)-1-Boc-3-Methylpiperazine 2756811, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); 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.163765-44-4,(R)-1-Boc-3-Methylpiperazine,as a common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 39 (5.0 g, 13.5 mmol) in DMF (42 mL) were added triethylamine (3.8 mL) and 1-(pyridin-3-ylmethyl)-piperazine (3.2 g, 18.1 mmol) at room temperature under nitrogen. The stirred mixture was heated at 50C for 3 h. The reaction mixture was cooled to room temperature and diluted with water, THF and EtOAc. The organic extract was washed with water, dried over Na2SO4, filtrated and then concentrated. The crude solid was washed with Et2O/EtOAc and filtrated to afford the title compound 40 as a white solid (6.33 g, 12.4 mmol, 91.5%)., 163765-44-4

The synthetic route of 163765-44-4 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Nagao, Satoshi; Yamane, Yoshinobu; Funasaka, Setsuo; Tanaka, Keigo; Miyazaki, Kazuki; Kotake, Yoshihiko; Kamata, Jun-Ichi; Watanabe-Miyano, Saori; Toyama, Osamu; Ozawa, Yoichi; Mizui, Yoshiharu; Okamoto, Kiyoshi; Ito, Daisuke; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5513 – 5529;,
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.163765-44-4,(R)-1-Boc-3-Methylpiperazine,as a common compound, the synthetic route is as follows.

To a stirred solution of tert-butyl (3R)-3-methylpiperazine-1-carboxylate (500 mg, 2.5mmol), 6-chloropyridine-3-carbonitrile (415 mg, 3 mmol) in DMSO (10 mL), potassiumcarbonate (690 mg, 5 mmol), Cu (MeCN)4PF6(18 mg, 0.05 mmol) were added at RT. Thereaction mixture was heated at 140 C for 4 h (TLC indicated complete consumption of thestarting materials), brought toRT, diluted with water (30 mL) and extracted with EtOAc (3 x40 mL). The combined organic extracts were washed with water (30 mL), brine (40 mL),dried over Na2S04 and concentrated under reduced pressure to afford the crude compound.The crude material was purified by column chromatography (100-200 mesh silica gel, 7 g,30% EtOAc-hexane) to afford tert-butyl (3R)-4-(5-cyano-2-pyridyl)-3-methyl-piperazine-1-carboxylate (415 mg, 55%) as an off-white solid.1H NMR [300 MHz, CDCh]: J 8.39 (d, J = 2.4 Hz, 1H), 7.62-7.58 (m, 1H), 6.54 (d, J = 9.0Hz, 1H), 4.51 (brs, 1H), 4.13-3.89 (m, 3H), 3.27-3.13 (m, 2H), 3.00 (brs, 1H), 1.45 (s, 9H),1.23-1.16 (m, 3H).LCMS: m/z: 247.46 [M-tBu] +., 163765-44-4

163765-44-4 (R)-1-Boc-3-Methylpiperazine 2756811, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

163765-44-4, (R)-1-Boc-3-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(c) (R)-4-[5-(4-Bromo-2-chloro-5-trifluoromethoxy-phenylcarbamol)-pyridin-2-yl]-3-methyl-piperazine-1-carboxylic acid tert-butyl ester To a reaction mixture of the product of the previous step (999 mg, 2.42 mmol) in a mixture of N,N-diisopropylethylamine (0.84 mL, 4.83 mmol); and DMSO (0.86 mL, 12.08 mmol) was added (R)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (726 mg, 3.62 mmol) and the reaction mixture was heated at 120 C. overnight and extracted with ethyl acetate/water. The organic layer was dried over sodium sulfate and concentrated under vacuum. The dark oil was dissolved in a small amount of DCM and purified by silica gel chromatography (24 g column, 0-40% ethyl acetate:hexanes) to produce the title intermediate as a white solid (916 mg, 64% yield). (m/z): [M+H]+ calcd for C23H25BrClF3N4O4 593.07, 595.07 found 595.4., 163765-44-4

As the paragraph descriping shows that 163765-44-4 is playing an increasingly important role.

Reference：
Patent; McKinnell, Robert Murray; Long, Daniel D.; US2013/287731; (2013); 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.163765-44-4,(R)-1-Boc-3-Methylpiperazine,as a common compound, the synthetic route is as follows.

A 100-mL round-bottom flask was charged with triphosgene (0.743 g, 2.50 mmol, 0.50 equiv), tert-butyl (R)-3-methylpiperazine-1-carboxylate (1.00 g, 5.00 mmol, 1.00 equiv), and dichloromethane (10 mL). DIPEA (1.94 g, 15.0 mmol, 3.00 equiv) was added at 0 C. The reaction was stirred for 3 hours at room temperature and quenched with water (80 mL). The mixture was extracted with dichloromethane (2*100 mL) and the organic layers were combined, washed with brine (2*80 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide 1.40 g of tert-butyl (R)-4-(chlorocarbonyl)-3-methylpiperazine-1-carboxylate as a yellow oil. LCMS (ESI, m/z): 263 [M+H]+.

163765-44-4, 163765-44-4 (R)-1-Boc-3-Methylpiperazine 2756811, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; CISAR, Justin S.; DUNCAN, Katharine K.; FENG, Yu; WIENER, John J.M.; WEBER, Olivia D.; (79 pag.)US2018/256566; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

163765-44-4, (R)-1-Boc-3-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step B: (R)-tert-Butyl 4-(cis-4-(2-chloro-5-nitropyridin-4- ylamino)cyclohexanecarbonyl)-3-methylpiperazine-l-carboxylate. A suspension of cis-4-(2-chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylic acid hydrochloride (0.5 g, 1.487 mmol) in thionyl chloride (10.86 mL, 149 mmol) was heated at 70C for 1.5 hours. The mixture was concentrated under reduced pressure and dried under high vacuum for 1 hour. The resulting solid was suspended in THF (14.87 mL) and cooled to 0C under nitrogen atmosphere. To this mixture was added (R)-tert-butyl 3- methylpiperazine-l-carboxylate (0.357 g, 1.785 mmol) as a solution in THF (5 mL). The ice bath was removed, and the reaction mixture was stirred overnight at RT. The resulting mixture was diluted with DCM (lOOmL) and washed with saturated aqueous NaHC03 solution (30 mL) and then with saturated aqueous ammonium chloride solution (2x). The organic phase was collected, dried over sodium sulfate, and concentrated under reduced pressure to afford (R)-tert-butyl 4-(cis-4-(2-chloro-5-nitropyridin-4- ylamino)cyclohexanecarbonyl)-3-methylpiperazine-l-carboxylate as a light yellow solid (0.55 g, 77 % yield). MS = 482.2 [M+H]. Calc’d for C22H32C1N505: 481.2.

163765-44-4, As the paragraph descriping shows that 163765-44-4 is playing an increasingly important role.

Reference：
Patent; AMGEN INC.; BODE, Christiane, M.; CHENG, Alan, C.; CHOQUETTE, Deborah; LEWIS, Richard, T.; POTASHMAN, Michele, H.; ROMERO, Karina; STELLWAGEN, John, C.; WHITTINGTON, Douglas, A.; WO2012/18668; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

163765-44-4, (R)-1-Boc-3-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To 5-bromo-2-nitro-pyridine (500 mg, 2.46 mmol) and (‘R)-3-methyl-piperazine-1 -carboxylic acid tert-butyl ester (592 mg, 2.96 mmol) in 1 ,4-dioxane is added Cs2C03 (963 mg, 2.96 mmol) and XantPhos (71.3 mg, 0.12 mmol). The mixture is degassed for 5 min. Pd2(dba)3 (123 mg, 0.12 mmol) is added, degassed for 5 min. and stirred for 15 h at reflux. The reaction mixture is filtered through Celite and washed with DCM (50ml_ x 2). The combined organic layers are washed with brine, dried with Na2S04, filtered and concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography (0602) (EtOAc/hexane) to afford the title product. (0603) Yield: 400 mg (50%), 163765-44-4

The synthetic route of 163765-44-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BRUNETTE, Steven; CUI, Jianwen; LOWE, Michael D.; SARKO, Christopher Ronald; SURPRENANT, Simon; TURNER, Michael Robert; WU, Xinyuan; SMITH KEENAN, Lana Louise; BOUYSSOU, Thierry; (183 pag.)WO2019/158572; (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.163765-44-4,(R)-1-Boc-3-Methylpiperazine,as a common compound, the synthetic route is as follows.

The (R) – 1-BOC-3-methyl-piperazine (300 mg, 1 . 5mmol) dissolved in acetonitrile (10 ml) in, adding DIEA (390 mg, 3mmol) and cyclopropyl methyl bromide (235 mg, 1 . 73mmol), 40 C reaction 2d, cessation of the reaction, the reaction liquid concentrated, column chromatography (DCM: the MeOH=40 […] 1) obtaining white semi-solid 320 mg, yield 84.2%., 163765-44-4

The synthetic route of 163765-44-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Institute Of Materia Medica Chinese Academy Of Medical Sciences; Xu, Bailing; Chen, Xiaoguang; Yao, Haiping; Ji, Ming; Jin, Jing; Zhou, Jie; Wang, Ke; Zhao, Dalong; (55 pag.)CN105461697; (2016); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics