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

To 1 ,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (1g) in DCM (5OmL) was added DIPEA (1.74ml_). 4-cyanobenzenesulfonyl chloride (1.1g) was then added slowly and the reaction mixture was stirred for 1 hour. To the reaction was added DCM (5OmL) and the solution was washed with saturated sodium bicarbonate solution and water. The organic layer was collected and evaporated to dryness under vacuum. The resulting oil was dissolved in 1 ,4-dioxane (1OmL) before the addition of 4M HCI in 1 ,4-dioxane (1OmL) and a few drops of water. The reaction was stirred for 1.5 hours. The reaction mixture was evaporated to dryness under vacuum then dissolved in MeOH. The MeOH solution was loaded onto a 1Og SCX column. The loaded column was then washed with 2 column volumes of MeOH and the desired product was eluted from the column with 1 M ammonia in MeOH. The fraction containing eluted product was evaporated to dryness under vacuum to yield the title compound as a yellow oil (895mg, 68%).MS ES+ve m/z 265 (M+H)

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

Reference：
Patent; GLAXO GROUP LIMITED; BESWICK, Paul, John; CAMPBELL, Alister; CRIDLAND, Andrew; GLEAVE, Robert, James; PAGE, Lee, William; WO2010/102663; (2010); 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) Step 1 The 7-(bromomethyl)-6-methoxybenzofuran-3(2H)-one (0.514 g, 2.00 mmol) described in [WO2011/136319] and potassium carbonate (0.276 g, 2.00 mmol) were added to 8 mL of methylene chloride and stirred at room temperature. Two milliliters of a methylene chloride solution of tert-butyl (S)-2-methylpiperazine-1-carboxylate (0.401 g, 2.00 mmol) was added dropwise, and stirring was continued for 24 hours at room temperature. The reaction solution was filtered, and the residue obtained by concentrating the filtrate was purified by silica gel chromatography (ethyl acetate/hexane) to obtain tert-butyl (S)-4-[(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]-2-methylpiperazine-1-carboxylate (0.531 g, 70%). 1H NMR (300 MHz, CDCl3) delta 1.12 (d, J=6.6 Hz, 3H), 1.36 (s, 9H), 1.98 (dt, J=0.6, 11.7 Hz, 1H), 2.17 (dd, J=4.2, 10.8 Hz, 1H), 2.57 (d, J=10.8 Hz, 1H), 2.72 (d, J=10.8 Hz, 1H), 2.97 (dt, J=3.9, 12.3 Hz, 1H), 3.60 (d, J=2.4 Hz, 2H), 3.69 (d, J=12.3 Hz, 1H), 3.85 (s, 3H), 4.09-4.14 (m, 1H), 4.55 (s, 2H), 6.62 (d, J=8.7 Hz, 1H), 7.54 (d, J=8.7 Hz, 1H).

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

Reference：
Patent; THE UNIVERSITY OF TOKYO; NAGANO, Tetsuo; NAKANO, Hirofumi; HASEGAWA, Tsukasa; SAITO, Nae; KOJIMA, Hirotatsu; OKABE, Takayoshi; MUKAIDA, Naofumi; (42 pag.)US2017/145005; (2017); 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.

169447-70-5, Step 1: (S)-tert-butyl 4-(4-fluorophenyl)-2-methylpiperazine-1-carboxylate A solution of (S)-tert-butyl 2-methylpiperazine-1-carboxylate (1.2 g, 6 mmol), 1-bromo-4-fluorobenzene (1.26 g, 7.2 mmol), t-BuONa (865 mg, 9 mmol), BINAP (150 mg, 0.24 mmol), Pd2 (dba)3 (110 mg, 0.12 mmol) in dry toluene (40 mL) was stirred under N2 at 80 C. for 16 hrs. The reaction mixture was concentrated and the residue was purified by chromatography (silica, EtOAc/PE=1/10) to afford (S)-tert-butyl-4-(4-fluorophenyl)-2-methylpiperazine-1-carboxylate (1.5 g, 5.1 mmol, 85%) as a yellow oil. ESI-MS (EI+, m/z): 295.1 [M+H]+.

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.

169447-70-5, Step 1: (S)-tert-butyl 4-(4-fluorophenyl)-2-methylpiperazine-1-carboxylate A solution of (S)-tert-butyl 2-methylpiperazine-1-carboxylate (1.2 g, 6 mmol), 1-bromo-4-fluorobenzene (1.26 g, 7.2 mmol), t-BuONa (865 mg, 9 mmol), BINAP (150 mg, 0.24 mmol), Pd2 (dba)3 (110 mg, 0.12 mmol) in dry toluene (40 mL) was stirred under N2 at 80 C. for 16 hrs. The reaction mixture was concentrated and the residue was purified by chromatography (silica, EtOAc/PE=1/10) to afford (S)-tert-butyl-4-(4-fluorophenyl)-2-methylpiperazine-1-carboxylate (1.5 g, 5.1 mmol, 85%) as a yellow oil. ESI-MS (EI+, m/z): 295.1 [M+H]+.

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

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

To a solution of 5-fluoro-2-methyl-3-nitrobenzaldehyde (D32, 10 g) and (S)-tert-butyl 2-methylpiperazine-1 -carboxylate (12.03 g) in DCM (120 mL) was added drops of acetic acid (3.28g). The mixture was stirred at RT for an hour. Sodium triacetoxyhydroborate (23.15 g) was added in ice-bath. The mixture was stirred at RT overnight and quenched with sat. NaHCO3 solution. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated in vacuo to afford the title compound (22.17 g). MS (ESI): C18H26FN304 requires 367; found 368 [M+H].

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

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; DENG, Jing; LEI, Hui; MA, Xin; REN, Feng; CAI, Wei; LIN, Xichen; WO2015/180613; (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.

A 100 mL round-bottom flask was charged with 4-(morpholin-4-yl)-2- (trifluoromethyl)benzaldehyde (1.00 g, 3.86 mmol, 1.00 equiv), tert-butyl (2S)-2- methylpiperazine-l-carboxylate (0.850 g, 4.24 mmol, 1.10 equiv), 1 ,2-dichloroethane (20 mL). The mixture was stirred for 30 min at room temperature. Sodium triacetoxyborohydride (2.40 g, 1 1.3 mmol, 3.00 equiv) was added. The resulting solution was stirred overnight at room temperature, diluted with H20 (20 mL), extracted with dichloromethane (3 x 15 mL). The organic layers were combined and washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (20/80) to provide 1.70 g (99% yield) of tert- butyl (2S)-2-methyl-4-[[4-(morpholin-4-yl)-2-(trifluoromethyl)phenyl]methyl]piperazine-l- carboxylate as yellow oil. LCMS (ESI, m/z): 444 [M+H]+., 169447-70-5

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

Reference：
Patent; ABIDE THERAPEUTICS; THE SCRIPPS RESEARCH INSTITUTE; CISAR, Justin, S.; GRICE, Chery, A.; JONES, Todd, K.; NIPHAKIS, Micah, J.; CHANG, Jae, Won; LUM, Kenneth, M.; CRAVATT, Benjamin, F.; WO2013/103973; (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.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 2: (S)-tert-butyl-2-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-7-yl)piperazine-1-carboxylate To a rt solution of 7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole (3.8 g, 11.64 mmol) in anhydrous toluene (100 mL) was added (S)-tert-butyl-2-methylpiperazine-1-carboxylate (2.79 g, 13.98 mmol), Pd2(dba)3 (1.07 g, 1.17 mmol), t-BuONa (2.24 g, 23.29 mmol), and BINAP (1.45 g, 2.33 mmol) under nitrogen. The reaction mixture was stirred at 80 C. for 3 hrs, then cooled to rt, diluted with H2O (200 mL), and extracted with EtOAc (100 mL*2). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography (silica, EtOAc/PE=1/10) to afford (S)-tert-butyl-2-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-7-yl)piperazine-1-carboxylate (2.6 g, 5.83 mmol, 50.1%) as a yellow oil. ESI-MS (EI+, m/z): 446.3 [M+H]+., 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

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

Descriptions 150 (S)-tert-butyl 4-(5-chloro-2-methyl-3-nitrobenzyl)-2-methylpiperazine-1-carboxylate (DiSO)To a solution of 5-chloro-2-methyl-3-nitrobenzaldehyde (D143, 20 g) in DCM (260 mL), (S)-tertbutyl 2-methylpiperazine- 1 -carboxylate (24.08 g) was added. The mixture was stirred for 10 mm atroom temperture, sodium triacetoxyhydroborate (25.4 g) was added portionwise. The reaction mixtiure was stirred overnight at 20 C. The mixture was washed with brine, dried with anhydrous Na2SO4. Filtered, the filtrate was concentrated to give crude product, which was purified by column chromatography (silica gel, petroleum ether/EtOAc = 20:1) to afford the title compound (37 g) as white solid. MS (ESI): C18H26C1N3O4 requires 383; found 384 [M+Hf., 169447-70-5

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

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DENG, Jing; LEI, Hui; MA, Xin; LIN, Xichen; WO2015/180612; (2015); 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

6-Chloropyridine-2-carbonitrile (250 mg, 1.8 mmol) and tert-butyl (2S)-2- methylpiperazine-1-carboxylate (433 mg, 2.17 mmol) were added to a reaction tube with DIPEA (377 pi, 2.17 mmol) in DMF (2.5 ml). The tube was then sealed and the reaction stirred at 80 C for 20 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc (25 ml) and sat aq NaHCO3 (25 ml). The organics were separated and the aqueous phase extracted with EtOAc (2 x 20 ml). The combined organics were washed with water (20 ml), brine (20 ml), dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified via flash column chromatography (gradient of 0 – 100% EtOAc in heptane followed by 0-100% MeOH in EtOAc). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a yellow oil (321 mg, 51 %).1HNMR(500 MHz, Chloroform-d) 7.51 (dd, J = 8.8, 7.2 Hz, 1H), 6.96 (d, J = 7.1 Hz, 1H), 6.76 (d, J = 8.8 Hz, 1H), 4.32 (s, 1H), 4.11 (s, 1H), 4.03 -3.88 (m, 2H), 3.36-3.19 (m, 2H), 3.11 – 2.98 (m, 1H), 1.48 (s,9H), 1.17 (d, J = 6.7 Hz, 3H).LCMS Method 2 – Tr = 1.23 mm (ES+) (M+H)+ 288.0, 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; (565 pag.)WO2018/89433; (2018); 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.

A solution of 2-bromo-5-fluoropyridine (3.52 g, 20 mmol), (S)-tert-butyl 2- methylpiperazine-1-carboxylate (2 g, 11.36 mmol), t-BuONa (1.922 g, 20 mmol), BINAP (623 mg, 1 mmol), and Pd2(dba)3 (458 mg, 0.5 mmol) in dry toluene (20 mL) was stirred under N2 at 80 C for 16 h. The reaction mixture was concentrated and the mixture was purified by chromatography (silica, EtOAc/PE =1/10) to afford (S)-tert-butyl 4-(5-fluoropyridin-2-yl)-2- methylpiperazine-1-carboxylate (2.9 g, 9.82 mmol, 86%) as a yellow oil. ESI-MS (EI, m/z):296.2 [M+H]., 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; (565 pag.)WO2018/89433; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics