Category: 169447-70-5

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.

Example 166 N1-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N1-[(6-methyl-3′-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-1,1-cyclopropanedicarboxamide A mixture of N1-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N1-[(3′-formyl-6-methyl-3-biphenylyl)methyl]-1,1-cyclopropanedicarboxamide (55 mg, 0.088 mmol), (R)-N’-Boc-2-methyl-piperazine (17.69 mg, 0.088 mmol), sodium triacetoxyborohydride (37.4 mg, 0.177 mmol) and acetic acid (6.07 muL, 0.106 mmol) in DCM (2 mL) was stirred at room temperature overnight. The reaction mixture was quenched with saturated NaHCO3 and extracted with DCM twice. The combined organic layers were concentrated under vacuum to give the crude residue. It was re-dissolved in 25% TFA in DCM (2 mL) and stirred at room temperature for 2 h. Solvent was evaporated under a stream of nitrogen and then purified by reverse phase hplc with a Gilson HPLC (acidic conditions: 0.1% TFA in the solvents), eluding with 10 to 60% CH3CN in water at a flow rate of 20 mL/min. The product fractions were combined, washed with saturated NaHCO3 and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give N1-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N1-[(6-methyl-3′-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-1,1-cyclopropanedicarboxamide as a solid (30 mg, 48.1%). LC-MS m/z 707 (M+H)+, 0.74 min (ret time); 1H NMR (400 MHz, DMSO-d6) delta 0.88 (d, J=6.27 Hz, 3H) 1.20 (t, J=7.53 Hz, 3H) 1.29-1.36 (m, 7H) 1.40-1.64 (m, 3H) 1.84-1.92 (m, 3H) 2.17 (s, 3H) 2.60-2.67 (m, 4H) 2.73-2.78 (m, 1H) 2.83 (q, J=7.36 Hz, 2H) 3.46 (s, 2H) 3.52 (td, J=11.36, 2.13 Hz, 2H) 3.80-3.87 (m, 2H) 4.04-4.11 (m, 1H) 4.21-4.44 (m, 6H) 6.74 (d, J=7.78 Hz, 1H) 7.04 (d, J=1.76 Hz, 1H) 7.07-7.11 (m, 1H) 7.14-7.21 (m, 3H) 7.26 (d, J=7.78 Hz, 1H) 7.34-7.38 (m, 1H) 7.99 (s, 1H) 8.43 (t, J=5.77 Hz, 1H) 9.02 (t, J=5.77 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£º
Patent; Glaxo Group Limited; US2009/203677; (2009); 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 stirred solution of 1 ,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (0.2g, 1 mmol) in DCM (5mL) was added triethylamine (0.35ml_) and 4- chlorobenzenesulphonyl chloride (0.42g, 2mmol). The mixture was stirred overnight at ambient temperature under argon. To the reaction was added 4- chlorobenzenesulfonyl chloride (0.2g, 0.95mmol) and the reaction stirred for a further 2 hours. The solvent was evaporated and the crude taken up in DCM (25ml_). To the solution was added PS-trisamine (3g) and the mixture stirred at room temperature for 2hours. To the mixture was then added PS-isocyanate (1.5g) and the mixture stirred for a further 30minut.es. The reaction was filtered and the solvent removed by evaporation. The crude product was taken up in DCM, washed twice with water (2 x 5OmL), dried (MgSO4) and filtered. The solvent was evaporated to yield crude product which was dried at 4O0C under vacuum for 1 hour to yield the title compound as an off-white solid (0.284g, 76%).1H NMR (CDCI3) 51.27 (3H, d, J=I), 1.42 (9H, s), 2.24 (1 H, m), 2.42 (1 H, dd, J=11 ,4), 3.16 (1 H, m), 3.49 (1 H, dt, J=11 , 2), 3.67 (1 H, m), 3.93 (1 H, m), 4.34 (1 H, br s), 7.52 (2H, m), 7.67 (2H, m)., 169447-70-5

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

Reference£º
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

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 5-fluoro-2-methyl-3-nitrobenzaldehyde (D24 10 g) and (S) -tert-butyl 2-methylpiperazine-1-carboxylate (12.03 g) in DCM (120 mL) was added drops of acetic acid (3.28 g).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. NaHCO3solution. The organic layer was dried with anhydrous Na2SO4 filtered and concentrated in vacuo to give the title compound (22.17 g) as a syrup. MS (ESI) C18H26FN3O4requires 367 found 368 [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£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; LEI, Hui; MA, Xin; REN, Feng; LIN, Xichen; MARQUIS, Robert W., Jr.; WO2015/180614; (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

A solution of fe/f-butyl (2S)-2-methylpiperazine-1 -carboxylate (22.2 g, 1 1 1 mmol), 2,4- dichloropyrimidine (15.0 g, 101 mmol), and triethylamine (30 mL) in dichloromethane (200 mL) was stirred at 30 C for 15 hours, whereupon it was washed sequentially with water (150 mL) and with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on silica gel (Gradient: 20% to 50% EtOAc in petroleum ether) afforded C36 as a white solid. Yield: 25.0 g, 79.9 mmol, 79%.

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

Reference£º
Patent; PFIZER INC.; ASPNES, Gary Erik; BAGLEY, Scott W.; CONN, Edward L.; CURTO, John M.; EDMONDS, David James; FLANAGAN, Mark E.; FUTATSUGI, Kentaro; GRIFFITH, David A.; HUARD, Kim; LIMBERAKIS, Chris; MATHIOWETZ, Alan M.; PIOTROWSKI, David W.; RUGGERI, Roger B.; (149 pag.)WO2019/239371; (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,169447-70-5

To a solution of iodobenzene (2.08 g, 10.19 mmol) in toluene (60 mL) at rt was added (S)-tert-butyl-2-methylpiperazine-l-carboxylate (1.7 g, 8.49 mmol), Pd2(dba)3 (778 mg, 0.85 mmol) , t-BuONa (2.44 g, 25.46 mmol), XantPhos (982 mg, 1.70 mmol) under nitrogen. The reaction mixture was stirred at 100 C for 16 h, then cooled to rt and diluted with EtOAc (60 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, concentrated, and purified by chromatography (silica, EtOAc/PE = 1/10) to afford (S)-tert-butyl- 2-methyl-4-phenylpiperazine-l-carboxylate (1.8 g , 6.5 mmol, 64%) as an oil. ESI-MS (EI+, m/z): 277.2 [M+H]+.

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

Reference£º
Patent; NAVITOR PHARMACEUTICALS, INC.; O’NEILL, David John; SAIAH, Eddine; KANG, Seong Woo Anthony; BREARLEY, Andrew; BENTLEY, Jonathan; (184 pag.)WO2018/89493; (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 1, 1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (Intermediate 26,100 mg, 0.5 mmol) in CH2CI2 (5 mL) was mixed with 3-bromo benzaldehyde (0.06 mL, 0.5 mmol) and NaB (OAc) 3H (0.16 g, 0.75 mmol). The resulting mixture was stirred for 12 hours, diluted with dichloromethane (30 mL) and washed with brine (50 mL). The organic layer was collected, dried over Na2SO4 and concentrated. Separation via a combiflash system then afforded the title compound (150 mg, 81%). LC/MS : m/z, 369 (M+H) ;’HNMR (MeOD) 1.26 (3H, d), 1.47 (9H, s), 2.0 (1H, m), 2.1 (1H, m), 2.6 (1H, m), 2.8 (1H, m), 3.1 (1H, m), 3.3 (2H, s), 3.4 (1 H, m), 3.5 (1 H, m), 3.8 (1 H, m), 4.2 (1 H, m), 4.88 (1 H, s), 7.25 (1 H, m), 7.3 (1 H, m), 7.4 (1 H, m), 7.55 (1 H, s)., 169447-70-5

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/87236; (2005); 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 I: tert-butyl (2S)-4-(4-bromophenyl)-2-methyl-piperazine-1-carboxylate (1-35) A mixture of 1-34 (10 g, 50 mmol), 1,4-dibromobenzene (29.4 g, 125 mmol), cesium carbonate (24.3 g, 75 mmol) and BINAP (1.5 g, 2.5 mmol) in 1,4-dioxane (250 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added tris(dibenzylideneacetone)dipalladium(0) (0.900 g, 2.5 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 90 C. for 18 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (250 mL), followed by extraction with ethyl acetate (250 mL*3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60-120 mesh) using 10% EtOAc in hexanes to give the desired product 1-35 as a white solid (5.5 g, 31%); LCMS: m/z 357.1 [M++1], 359.1 [M++2].

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (132 pag.)US2017/8885; (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.

Step 1: (S)-tert-butyl-2-methyl-4-phenylpiperazine-1-carboxylate To a solution of iodobenzene (2.08 g, 10.19 mmol) in toluene (60 mL) at rt was added (S)-tert-butyl-2-methylpiperazine-1-carboxylate (1.7 g, 8.49 mmol), Pd2(dba)3 (778 mg, 0.85 mmol), t-BuONa (2.44 g, 25.46 mmol), XantPhos (982 mg, 1.70 mmol) under nitrogen. The reaction mixture was stirred at 100 C. for 16 h, then cooled to rt and diluted with EtOAc (60 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and purified by chromatography (silica, EtOAc/PE=1/10) to afford (S)-tert-butyl-2-methyl-4-phenylpiperazine-1-carboxylate (1.8 g, 6.5 mmol, 64%) as an oil. ESI-MS (EI+, m/z): 277.2 [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£º
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 1 ,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (1.5g, 7.5 mmol) in anhydrous DCM (3OmL) was added triethylamine (2.59ml_, 19 mmol) and phenyl-isocyanate (0.814ml_, 7.5 mmol) the mixture was stirred under an argon atmosphere at room temperature for 2hours. The reaction was evaporated and the residue was suspended DCM (3OmL) which was washed with (0.5M, aq) HCI (10OmL), and then water (10OmL). The collected organic layer was dried (MgSO4), filtered and evaporated to yield the title compound (1.96g, 82%)1H NMR (CDCI3) 51.21 (3H, d, J=6.8Hz), 1.48 (9H, s), 3.07 (1 H, br m), 3.20 (1 H, m), 3.30 (1 H, dd, J=13.37, 4.17Hz), 3.72 (1 H, m), 3.90 (2H, m), 4.28 (1 H, br m), 6.36 (1 H, NH, br m), 7.05 (1 H, m), 7.30 (2H, m), 7.35 (2H, m)., 169447-70-5

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

Reference£º
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

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 0 C solution of 2,4-dichloro-5-fluoropyrimidine (12.0 g, 71 .9 mmol) in dichloromethane (130 mL) was added triethylamine (20 mL, 140 mmol), followed by a solution of fe/f-butyl (2S)-2-methylpiperazine-1 -carboxylate (15.0 g, 74.9 mmol) in dichloromethane (70 mL). The reaction mixture was stirred at 30 C for 15 hours, whereupon it was washed sequentially with water (150 mL) and with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via chromatography on silica gel (Gradient: 20% to 50% EtOAc in petroleum ether) afforded C35 as a white solid. Yield: 21 .4 g, 64.7 mmol, 90%. LCMS m/z 330.9 [M+H]+. 1H NMR (400 MHz, CDCI3) d 7.94 (d, 1 H), 4.54- 4.45 (m, 1 H), 4.39-4.29 (m, 1 H), 4.28 (br d, 1 H), 3.94 (br d, 1 H), 3.35 (dd, 1 H), 3.25-3.06 (m, 2H), 1 .48 (s, 9H), 1 .17 (d, 3H).

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

Reference£º
Patent; PFIZER INC.; ASPNES, Gary Erik; BAGLEY, Scott W.; CONN, Edward L.; CURTO, John M.; EDMONDS, David James; FLANAGAN, Mark E.; FUTATSUGI, Kentaro; GRIFFITH, David A.; HUARD, Kim; LIMBERAKIS, Chris; MATHIOWETZ, Alan M.; PIOTROWSKI, David W.; RUGGERI, Roger B.; (149 pag.)WO2019/239371; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics