Category: 169447-70-5

169447-70-5, (S)-tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The mixture of 13a (151 mg, 0.423 mmol) and 4 N HCl in 1,4-dioxane solution (1.38 ml) was stirred at room temperature overnight. After concentration, the residue was crystalized with etherto afford the white precipitation. The resulting solid was collected by filtration to afford 14a (121 mg, 98.0%) as the white solid. MSESI (m/z) = 257 [M+H]+. To a solution of 4a (116 mg, 0.35 mmol)in DMF (2.3 ml) was added 14a (120 mg, 0.42 mmol), COMU (225 mg, 0.525 mmol) and Et3N (177 mg, 1.75 mmol) at room temperature.The reaction mixture was stirred at same temperature for 1.5 h. The reaction mixture was diluted with sat. NaHCO3 solution to afford the pale yellow precipitation. The resulting solid was collected by filtration to 16a, 169447-70-5

The synthetic route of 169447-70-5 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Tsuno, Naoki; Yukimasa, Akira; Yoshida, Osamu; Suzuki, Shinji; Nakai, Hiromi; Ogawa, Tomoyuki; Fujiu, Motohiro; Takaya, Kenji; Nozu, Azusa; Yamaguchi, Hiroki; Matsuda, Hidetoshi; Funaki, Satoko; Yamanada, Natsue; Tanimura, Miki; Nagamatsu, Daiki; Asaki, Toshiyuki; Horita, Narumi; Yamamoto, Miyuki; Hinata, Mikie; Soga, Masahiko; Imai, Masayuki; Morioka, Yasuhide; Kanemasa, Toshiyuki; Sakaguchi, Gaku; Iso, Yasuyoshi; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2177 – 2190;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

169447-70-5, (S)-tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0144] Step 6a: (S)-tert-Butyl 4-acryloyl-2-methylpiperazine-1-carboxylate . Acryloyl chloride (1.3 mL, 16.5 mmol) was added to a solution of (S)-1-Boc-2-methyl-piperazine (3.00 g, 15.0 mmol, Boc Sciences, Shirley, NY) in THF (30 mL) at-10 C, and the resulting mixture was stirred at-10 C for 5 min. Triethylamine (6.3 mL, 44.9 mmol) was then slowly added, and the resulting mixture was stirred at-10 C for 15 min, then allowed to warm to rt. The reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the organic layers were then combined, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography (eluent: 0-100% EtOAc/heptane) to provide (S)-tert-butyl 4-acryloyl-2- methylpiperazine-1-carboxylate: 1H NMR (400 MHz, DMSO-d6) d 6.72- 6.85 (m, 1H) 6.10 – 6.18 (m, 1H) 5.68- 5.76 (m, 1H) 4.08- 4.32 (m, 2H) 3.68- 4.03 (m, 2H) 2.86- 3.14 (m, 2H) 2.66- 2.80 (m, 1H) 1.38- 1.43 (s, 9H) 0.96- 1.04 (m, 3H). m/z (ESI, +ve ion): 277.3 (M+Na)+.

169447-70-5, As the paragraph descriping shows that 169447-70-5 is playing an increasingly important role.

Reference：
Patent; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

169447-70-5, (S)-tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Heat a mixture of l,4-dichloro-2,3-dimethylpyridazine (6.06 g, 34.2 mmol), (S)-2- methyl-piperazine-1-carboxylic acid tert-butyl ester (6.88 g, 34.4 mmol) and dsopropylethylamine (30 ml, 172 mmol) in DMSO (30 mL) at 120 0C for 5 d. Cool and treat the mixture with additional (5)-2-methyl-piperazine-l-carboxylic acid tert-butyi ester (3.74 g, 18.7 mmol), and resume heating at 120 0C for an additional 2 d. Dilute the reaction mixture with EtOAc and wash with H2O and brine. Dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 20 to 50% EtOAc in hexanes) to afford the title compound as a pale yellow foam (7.36 g, 63%). ES/MS m/z (35Cl) 341.0 (M+l)., 169447-70-5

Big data shows that 169447-70-5 is playing an increasingly important role.

Reference：
Patent; ELI LILLY AND COMPANY; CLAY, Julia, Marie; HIPSKIND, Philip, Arthur; SALL, Daniel, Jon; WILSON (NEE TAKAKUWA), Takako; THOMPSON, Michelle, Lee; BASTIAN, Jolie, Anne; WO2010/56620; (2010); 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.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 1: (S)-tert-butyl 2-methyl-4-(3-nitrophenyl)piperazine-1-carboxylate A mixture of K2CO3 (8.8 g, 63.8 mmol), 1-fluoro-3-nitrobenzene (3 g, 21.3 mmol), and (S)-tert-butyl-2-methylpiperazine-1-carboxylate (4.26 g, 21.3 mmol) in DMSO (80 mL) was stirred at 130 C. for 16 hrs. The mixture was then filtered and the filtrate was washed with water, extracted with EtOAc, and purified by chromatography (silica, EtOAc/PE=1/10) to afford (S)-tert-butyl-2-methyl-4-(3-nitrophenyl)piperazine-1-carboxylate (1.98 g, 6.18 mmol, 29%). ESI-MS (EI+, m/z): 222.2 [M-99]+., 169447-70-5

The synthetic route of 169447-70-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (136 pag.)US2019/389843; (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.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 1: Synthesis of (S)-tert-butyl-2-methyl-4-(pyrimidin-2-yl)piperazine-1-carboxylate To the mixture of 2-chloropyrimidine (200 mg, 1.75 mmol), (S)-tert-butyl-2-methylpiperazine-1-carboxylate (350 mg, 1.75 mmol), and DIPEA (677 mg, 5.24 mmol) was added DMF (4 mL). The mixture was stirred at 100 C. for 3 hrs, then extracted with EtOAc/H2O (50 mL/50 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (silica, PE/EtOAc=0-10%) to afford (S)-tert-butyl-2-methyl-4-(pyrimidin-2-yl)-piperazine-1-carboxylate (330 mg, 67.8%). MS (EI+, m/z): 279 [M+H]+., 169447-70-5

As the paragraph descriping shows that 169447-70-5 is playing an increasingly important role.

Reference：
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (136 pag.)US2019/389843; (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.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl (2S)-2- methylpiperazine-l-carboxylate (400 mg, 2.00 mmol) in dichloromethane (6 mL) was added acetic acid (120 mg, 2.0 mmol) and 5-cyclopropyl-3-(2,6-dichlorophenyl)-l,2-oxazole-4- carbaldehyde (562 mg, 1.99 mmol). After the mixture was stirred for 30 min, NaBH(OAc)3 (1.3 g, 6.13 mmol) was added. The resulting solution was stirred overnight at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (30:70). This resulted in 670 mg (72%) of the title compound as a white solid. LC-MS (ESI, m/z): [M+H]+ = 466.2., 169447-70-5

The synthetic route of 169447-70-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; HEPAGENE THERAPEUTICS, INC.; XU, Xiaodong; (104 pag.)WO2018/85148; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

169447-70-5, (S)-tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of (S)-tert-butyl 2-methylpiperazine-1- carboxylate (1.42 g, 7.09 mmol), 1-fluoro-4-nitrobenzene(1 g, 7.09 mmol) and potassium carbonate (1.47 g, 10.6 mmol) in DMF (6 mL) was heated at 50 C for 20 h. The reaction mixture was cooled to room temperature and diluted with water (50 mL) . The resulting precipitate was collected by filtration and washed with water to give thetitle compound (1.83 g, 80%) . LCMS (Method A) : = 1.45 mi m/z = 266 [M+H-tBu]., 169447-70-5

The synthetic route of 169447-70-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ALMAC DISCOVERY LIMITED; HARRISON, Timothy; TREVITT, Graham; HEWITT, Peter Robin; O’DOWD, Colin Roderick; BURKAMP, Frank; WILKINSON, Andrew John; SHEPHERD, Steven D.; MIEL, Hugues; WO2015/92431; (2015); 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.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

^-ieri-Butyl 2-methyl-4-(pyridin-2-yl)piperazine-l-carboxylateTo a solution of ieri-butyl (25)-2-methylpiperazine-l-carboxylate (8 g, 39.94 mmol) in DMSO (25 ml) was added 2-bromopyridine (6.594 g, 41.74 mmol), and DIEA (15.48 g, 119.78 mmol). After stirring 2 days at 120C, the resulting solution was quenched by the addition of DCM (200 ml), washed with water (3 x 300 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified via silica gel chromatography (3% ethyl acetate in petroleum ether) to afford (S)-tert- butyl 2-methyl-4-(pyridin-2-yl)piperazine-l-carboxylate as a red oil (5.2 g, 47%).LC/MS (ES, m/z): [M+H]+ 278.0’H-NMR (300 MHz, CDC13) delta 8.18 – 8.20 (t, J = 1.8 Hz, 1H), 7.46 – 7.52 (m, 1H), 6.60 – 6.64 (m, 2H), 4.33 – 4.35 (m, 1H), 4.08 – 4.15 (m, 1H), 3.91 – 4.00 (m, 2H), 3.19 – 3.31 (m, 2H), 2.92 – 3.01 (m, 1H), 1.50 (s, 9H), 1.27 – 1.30 (t, / = 4.5 Hz, 3H)

169447-70-5, Big data shows that 169447-70-5 is playing an increasingly important role.

Reference：
Patent; BIOENERGENIX; MCCALL, John M.; ROMERO, Donna L.; KELLY, Robert C.; WO2012/119046; (2012); A2;,
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.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of the product of step A (500 mg, 2.5 mmol), methyl 4-(bromomethyl)-3- (trifluoromethyl)benzoate (891 mg, 3.0 mmol) and Et3N(505 mg, 5.0 mmol) in DCM (20 mL) was stirred at room temperature for 2 hours. The reaction mixture was diluted with DCM (lOOmL), washed with brine (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica weight: 10 g, eluted with petroleum ether/EA: 10/1) to give the title compound (700 mg, 70%) as oil. 1H MR (400 MHz, CDC13) delta 8.31 (s, 1H), 8.19 (d, J= 8.0 Hz, 1H), 7.95 (d, J= 8.0 Hz, 1H), 4.26-4.16 (m, 1H), 3.95 (s, 3H), 3.86-3.80 (m, 1H), 3.66 (s, 2H), 3.18 – 3.07 (m, 1H), 2.76- 2.68 (m, 1H), 2.58-2.51 (m, 1H), 2.30-2.23 (m, 1H), 2.18 – 2.08 (m, 1H), 1.46 (s, 9H), 1.28- 1.25 (m, 3H)ppm.

169447-70-5, The synthetic route of 169447-70-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BEIGENE, LTD.; ZHOU, Changyou; ZHANG, Guoliang; WO2014/206344; (2014); 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.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Preparation 10 tert-Butyl (S)-4-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2-methylpiperazine-1-carboxylate To a 250 mL round-bottom flask were added (S)-tert-butyl 2-methylpiperazine-1-carboxylate (3.94 g, 19.7 mmol) and (S)-1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (2.5 g, 9.8 mmol) in 1,4-dioxane (23 mL). To the resulting solution was added potassium 2-methylpropan-2-olate (1 M in THF, 21 mL, 21 mmol), and the mixture was heated to 90 C. for 1 hour. After cooling for 10 minutes, the red mixture was poured into 300 mL of saturated NaHCO3 and then extracted with EtOAc (3*). The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo to give crude product, which was purified by preparative HPLC (acid mode, 25-50% ACN/water gradient). The product-containing fractions were combined, concentrated in vacuo, and partitioned between saturated NaHCO3 and EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound (1.41 g, 38.4%). ESI-MS m/z [M+H]+ calc’d for C20H31N5O2, 374. found 374., 169447-70-5

As the paragraph descriping shows that 169447-70-5 is playing an increasingly important role.

Reference：
Patent; Chang, Edcon; Smith, Christopher; Wang, Xiaolun; Wallace, Michael B.; US2015/191465; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics