Category: 548762-66-9

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.548762-66-9,(2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a stirred solution of tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (500 mg, 2.33 mmol) in dry acetonitrile (10 mL), methyl 2-bromopropanoate (468 mg, 2.80 mmol) and DIPEA (1.22 mL, 7.00 mmol) were added at room temperature. The reaction mixture was heated to 85 C for 16 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to obtain the crude product, which was purified by Combi flash 24 g silica gel chromatography by using 0-30% ethyl acetate in petroleum ether as eluent to obtain tert-butyl (2S,5R)-4-(1-methoxy-1-oxopropan-2- yl)-2,5-dimethylpiperazine-1-carboxylate (620 mg, 88 % yield) as a light yellow liquid. LCMS: m/z, 301.2 (M+H); retention time 2.941 and 3.094 min. Column: Kinetex XB- C18 (3 x 75 mm) 2.6 mm; Mobile phase A: 10 mM ammonium formate: acetonitrile (98:2), Mobile phase B: 10 mM ammonium formate: acetonitrile (2:98), Gradient = 20- 100 % B over 4 minutes, then a 0.6 minute hold at 100 % B; Temperature: 27 C; Flow rate: 1.0 mL/min; Detection: UV at 220 nm, 548762-66-9

As the paragraph descriping shows that 548762-66-9 is playing an increasingly important role.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); 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.548762-66-9,(2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

548762-66-9, To a stirred solution of tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (0.35 g, 1.63 mmol) in acetonitrile (8 mL) were added DIPEA (0.9 mL, 4.9 mmol) and methyl 2-bromo-2-(5-(trifluoromethyl)pyridin-2-yl)acetate (0.54 g, 1.79 mmol) at room temperature. The reaction mixture was heated at 85 C for 16 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure to obtain the crude product, which was purified by silica gel chromatography (24 g; using 6 % -10 % ethyl acetate/ petroleum ether) to obtain tert-butyl (2S,5R)-4-(2-methoxy-2-oxo-1-(5- (trifluoromethyl)pyridin-2-yl)ethyl)-2,5-dimethylpiperazine-1-carboxylate (0.52 g, 74 % yield). LCMS: m/z = 432.2 (M+H); retention time 2.19 min [LCMS method: Column: Waters Acquity UPLC BEH C18 (2.1 x 50 mm), 1.7 mm; Mobile phase A: 0.1% TFA in water; Mobile phase B: 0.1 % TFA in acetonitrile; Gradient = 20-90 % B over 1.1 minute, then a 0.6 minute hold at 90 % B; Temperature: 50 C; Flow rate: 0.7 mL/min; Detection: UV at 220 nm].

The synthetic route of 548762-66-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

548762-66-9, (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

548762-66-9, To a stirred solution of tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (0.5 g, 2.33 mmol) in acetonitrile (10 mL) were added sodium bicarbonate (0.98 g, 11.67 mmol) and 1-bromo-4-(1-bromoethyl)-2-fluorobenzene (0.66 g, 2.33 mmol) at room temperature. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure to obtain the crude product, which was purified by flash column chromatography (Column: 24 g silica; Solvent run: 40-45% EtOAc in petroleum ether) to obtain a diastereomeric mixture of tert-butyl (2S,5R)-4-(1-(4-bromo-3-fluorophenyl)ethyl)-2,5- dimethylpiperazine-1-carboxylate (0.3 g, 27 % yield) as an off-white solid. LCMS: m/z, 416.2 (M+2); retention time 3.55 min. (LC-MS Method info: Column-KINETEX- XB- C18 (75 x 3 mm- 2.6 ^m ); Mphase A: 10 mM ammonium formate in water: acetonitrile (98:2); Mphase B: 10 mM ammonium formate in water: acetonitrile (2:98); Gradient: 20- 100% B over 4 minutes, flow rate 1.0 mL/min, then a 0.6 minute hold at 100% B flow rate 1.5 mL/min; then Gradient: 100-20% B over 0.1 minutes, flow rate 1.5 mL/min).

The synthetic route of 548762-66-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

548762-66-9, (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

548762-66-9, To a stirring suspension of 1-fluoro-4-nitrobenzene (0.60 g, 4.24 mmol) and potassium carbonate (2.34 g, 16.97 mmol) in anhydrous DMF (5 mL) was added (2S,5R)-tert- butyl 2,5-dimethylpiperazine-1-carboxylate (1 g, 4.67mmol) and the mixture heated at 90 C for 120 h. After cooling the mixture was partitioned between brine/water (1:1, 50 mL) and ethyl acetate (25 mL) . The aqueous layer was separated and extracted with ethyl acetate (3 x 25 mL) . The combined ethyl acetate fractions were washedwith brine/water (1:1, 4 x 12.5 mL), dried (anhydrous sodium sulfate), filtered and reduced in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0-50% Ethyl Acetate in Cyclohexane) to afford the title compound (1.03 g, 72.4%) . ?H NMR (400 MHz, CDC13) : 3 8.12 (d, 2H), 6.77 (d,2H), 4.24-4.58 (m, 1H), 4.03-4.16 (m, 1H), 3.73-3.93 (m,1H), 3.31-3.49 (m, 3H), 1.49 (s, 9H), 1.24 (d, 3H), 1.18(d, 3H) . LCMS (Method C) : = 1.80 mm, m/z = 336 [M+H].

548762-66-9 (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate 11745988, apiperazines compound, is more and more widely used in various fields.

Reference£º
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.548762-66-9,(2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a stirred solution of tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (0.2 g, 0.93 mmol) in acetonitrile (6 mL) were added DIPEA (0.5 mL, 2.80 mmol) and dimethyl 4,4′-(bromomethylene)dibenzoate (0.373 g, 1.03 mmol) at room temperature. The reaction mixture was heated at 85 C for 16 h. The volatiles were removed from the reaction mixture under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography (24 g, 12 %-17 % ethyl acetate/ petroleum ether) to obtain dimethyl 4,4′-(((2R,5S)-4-(tert-butoxycarbonyl)-2,5-dimethylpiperazin-1-yl) methylene)dibenzoate (140 mg, 30.2 % yield). LCMS: m/z = 497.2 (M+H); retention time 2.52 min [LCMS method: Column: Waters Acquity UPLC BEH C18 (2.1 x 50 mm) 1.7 mm, Mobile phase A: 10 mM NH4OAc: acetonitrile (95:5); Mobile phase B: 10 mM NH4OAc:acetonitrile (5:95), Gradient = 20-90 % B over 1.1 minute, then a 0.6 minute hold at 90 % B; Temperature: 50 C; Flow rate: 0.7 mL/min; Detection: UV at 220 nm]., 548762-66-9

548762-66-9 (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate 11745988, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

548762-66-9, (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,548762-66-9

(a) (2S,5R)-2,5-Dimethyl-4-(5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester A mixture of 2-chloro-5-nitropyridine (1.0 g, 6.3 mmol), (2S,5R)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 6.3 mmol), and potassium carbonate (1.7 g, 13 mmol) was stirred in DMSO (5.0 mL, 70 mmol) at 100 C. overnight. The reaction mixture was filtered thru a silica gel pad, which was washed with EtOAc (200 mL). The filtrate was washed with water (2*10 mL), concentrated, and purified by silica gel chromatography (eluted with ethyl acetate/hexane=0 to 80%) to give the title intermediate (1.724 g, 81% yield) as a yellow solid.

548762-66-9 (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate 11745988, apiperazines compound, is more and more widely used in various fields.

Reference£º
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

548762-66-9, (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (1.5 g, 7. mmol) in acetonitrile (15 mL) was added DIPEA (3.7 mL, 21 mmol) and methyl 2-bromo-2-(4-fluorophenyl)acetate (1.9 g, 7.7 mmol). The reaction mixture was heated up to 85 C over 10 min and was stirred for 16 h. The reaction mixture was concentrated under reduced pressure to obtain a brown gummy solid. The crude compound was purified by flash chromatography (using 24 g silica gel column; using 5 % -10 % ethylacetate/ Pet. ether) to obtain tert-butyl (2S,5R)-4-(1-(4-fluorophenyl)-2-methoxy-2- oxoethyl)-2,5-dimethylpiperazine-1-carboxylate (2.35 g, 6.18 mmol, 88% yield) as brown solid. LCMS: m/z, 379.3 (M-H); rt 1.13 min; Column: Waters Acquity UPLC BEH C18 (2.1 x 50 mm) 1.7 mm, Mobile phase A: 10 mM ammonium acetate:acetonitrile (95:5); Mobile phase B: 10 mM ammonium acetate:acetonitrile (5:95), Gradient = 20-90 % B over 1.1 minute, then a 0.6 minute hold at 90 % B; Temperature: 50 C; Flow rate: 0.7 mL/min; Detection: UV at 220 nm., 548762-66-9

As the paragraph descriping shows that 548762-66-9 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); 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.548762-66-9,(2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

(a) (2S,5R)-4-(5-Methoxycarbonyl-pyridin-2-yl)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester A mixture of 6-fluoronicotinic acid methyl ester (200 mg, 1.29 mmol) and (2S,5R)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester was heated at 120 C in DMSO (2.0 mL) with potassium carbonate (178 mg, 1.29 mmol) for 2 h. The reaction mixture was partitioned between ethyl acetate (20.0 mL) and water (5.0 mL). The organic layer was washed with water (2 x 5.0 mL), dried over sodium sulfate, filtered and concentrated to give the title intermediate as a yellowish oil.

548762-66-9, 548762-66-9 (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate 11745988, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Theravance Biopharma R&D IP, LLC; MCKINNELL, Robert Murray; LONG, Daniel D.; VAN ORDEN, Lori Jean; JIANG, Lan; LOO, Mandy; SAITO, Daisuke Roland; ZIPFEL, Sheila; STANGELAND, Eric L.; LEPACK, Kassandra; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; EP2635571; (2015); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

548762-66-9, (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

548762-66-9, The solid from the previous step was dissolved in a mixture of N,N-diisopropylethylamine (0.7 mL, 4 mmol) and DMSO (0.7 mL, 10 mmol) and (2S,5R)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (590 mg, 2.7 mmol) was added and the reaction mixture heated at 120 C overnight, concentrated by rotary evaporation, dissolved in a small amount of DCM and purified by silica gel chromatography (0-40% ethyl acetate:hexanes) to produce the title intermediate (613 mg, 57 % yield) as a white solid. (m/z): [M+H]+ calcd for C24H27F4N4O4 591.12 found 591.4.

The synthetic route of 548762-66-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Theravance Biopharma R&D IP, LLC; MCKINNELL, Robert Murray; LONG, Daniel D.; VAN ORDEN, Lori Jean; JIANG, Lan; LOO, Mandy; SAITO, Daisuke Roland; ZIPFEL, Sheila; STANGELAND, Eric L.; LEPACK, Kassandra; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; EP2635571; (2015); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

548762-66-9, (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,548762-66-9

A solution of 6-chloro-1-(3,5-diisopropylpyridazin-4-yl)-7-(2-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.439 g, 0.967 mmol, Intermediate 212), phosphoryl trichloride (0.108 mL, 1.16 mmol), and DIPEA (0.168 mL, 0.967 mmol) in acetonitrile (5 mL) was stirred under an air condensor and drying tube at 80 C. for 30 min. The reaction mixture was cooled to RT, and tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (0.207 g, 0.967 mmol; eNovation Chemicals LLC, Bridgewater, N.J.) was added; the solution was stirred a RT for 30 min. The reaction mixture was diluted with EtOAc (200 mL), added to a separatory funnel, and washed with saturated, aqueous sodium bicarbonate (2*100 mL); the organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel. 0-100% EtOAc/heptane) to give tert-butyl (2S,5R)-4-(6-chloro-1-(3,5-diisopropylpyridazin-4-yl)-7-(2-fluorophenyl)-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-4-yl)-2,5-dimethylpiperazine-1-carboxylate (258 mg, 0.397 mmol, 41% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.11 (d, J=2.3 Hz, 1H) 8.13 (d, J=1.9 Hz, 1H) 7.38-7.47 (m, 1H) 7.05-7.18 (m, 3H) 4.16-5.08 (m, 3H) 3.76-4.08 (m, 2H) 3.45-3.65 (m, 1H) 2.70-2.82 (m, 1H) 2.58-2.70 (m, 1H) 1.52 (s, 9H) 1.24-1.37 (m, 12H) 1.17 (dd, J=9.1, 6.8 Hz, 3H) 1.04 (dd, J=6.7, 4.7 Hz, 3H). 19F NMR (377 MHz, CDCl3) delta -113.34–113.24 (m, 1F). MS (ESI, +ve) m/z: 650.2 (M+1)+.

As the paragraph descriping shows that 548762-66-9 is playing an increasingly important role.

Reference£º
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics