Analyzing the synthesis route of (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate

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

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

New learning discoveries about 314741-39-4

As the paragraph descriping shows that 314741-39-4 is playing an increasingly important role.

314741-39-4, (S)-1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,314741-39-4

1-tert-Butyl 3-methyl (3S)-piperazine-1,3-dicarboxylate (10 g, 40.9 mmol), (4-fluorophenyl)boronic acid (11.5 g, 82.1 mmol), copper(II) acetate (7.44 g, 40.9 mmol) and pyridine (6.67 ml, 82.6 mmol) were suspended in anhydrous 1,2-dichloroethane (300 ml) and the mixture was stirred at ambient temperature for 72 hours. A continuous airflow was bubbled through the reaction and the mixture stirred for 44 hours at ambient temperature. The airflow was removed and the reaction stirred at 45 C. for 20 hours, then cooled to ambient temperature. The mixture was filtered through celite, washed with DCM. The filtrate was concentrated in vacuo and the green oil obtained was purified via flash column chromatography eluting with gradient from 0-100% EtOAc in heptane followed by 0-100% MeOH in EtOAc. The product containing fractions were combined and concentrated in vacuo to afford the title compound as a yellow oil (4.29 g, 29%). 1H NMR (500 MHz, Chloroform-d) delta 6.98-6.92 (m, 2H), 6.85-6.80 (m, 2H), 4.47 (d, J=12.7 Hz, 1H), 4.27 (s, 1H), 4.21-3.92 (m, 1H), 3.64 (s, 3H), 3.60-3.47 (m, 1H), 3.37 (d, J=10.6 Hz, 1H), 3.27-2.99 (m, 2H), 1.46 (s, 9H). LCMS Method 3 Tr=1.88 min, (ES+) (M+H+)339.1.

As the paragraph descriping shows that 314741-39-4 is playing an increasingly important role.

Reference£º
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of 262368-30-9

262368-30-9 N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 21927707, apiperazines compound, is more and more widely used in various fields.

262368-30-9, N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add to the reaction flask(E) -4 – [(2-methoxybenzylidene)Methyl acetate-2-yl]3-nitrobenzoate (III) (3.71 g, 10 mmol),N- (4-aminophenyl) -N-methyl-2- (4-methylpiperazin-1-yl)Acetamide (IV)(2.88 g, 11 mmol)And 50 mL of N, N-dimethylformamide, the temperature was raised to 80-85 C, and the reaction was stirred for 2 hours.The mixture was cooled to room temperature, pyridine (5 mL) was added and the mixture was stirred at room temperature for 2 hours.The reaction solution was poured into 150 mL of water to precipitate a solid. Filtered, the crude product recrystallized from ethanol,A yellow solid was obtained(Z) -4 – {[2- (N-methyl-2- (4-methylpiperazin-1-yl)Acetamidanilide) benzylidene]Methyl-2-yl} -3-nitrobenzoate (V)4.32 g, yield 71.9%., 262368-30-9

262368-30-9 N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 21927707, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Suzhou Mirac Pharma Technology Co.,Ltd; Xu, Xuenong; (7 pag.)CN104262232; (2016); B;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline

122833-04-9, As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

122833-04-9, 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0105] To a solution of compound 7 (260 mg, 0.6 mmol) inbutan-2-ol (1 mL) were added 2-methoxy-4-( 4-methylpiperazin-1-yl)aniline (133 mg, 0.6 mmol) and trifluoroacetic acid( 48 flL, 0.6 mmol). The reaction mixture was heated to 110C. and reacted in a sealed tube for 24 h, diluted by DCM,washed by saturated NaHC03 solution, washed by saturatedbrine, dried by anhydrous Na2S04 , evaporated the solventunder reduced pressure, and then purified by colunm chromatographyto yield a yellow solid (151 mg, 44%).[0106] 1H NMR (400Hz, CDCI3 ) o 7.99 (s, lH), 7.48 (d,1=7.5 Hz, lH), 7.44 (s, lH), 7.41 (t, 1=8.0 Hz, lH), 7.35 (s,lH), 6.97 (d, 1=7.5 Hz, lH), 6.63 (s, lH), 6.42 (d, 1=2.0 Hz,lH), 6.16 (d, 1=6.4 Hz, lH), 4.42 (s, 2H), 3.80 (s, 3H), 3.22(m, 4H), 3.08 (s, 3H), 2.79 (m, 4H), 1.47 (s, 9H).[01 07]

122833-04-9, As the paragraph descriping shows that 122833-04-9 is playing an increasingly important role.

Reference£º
Patent; GUANGZHOU INSTITUTE OF BIOMEDICINE AND HEALTH, CHINESE ACADEMY OF SCIENCES; Ding, Ke; Chang, Shaohua; Xu, Shilin; Zhang, Lianwen; Tu, Zhengchao; Ding, Jian; Geng, Meiyu; Chen, Yi; US2014/296216; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of Methyl 1-Boc-piperazine-2-carboxylate

129799-15-1 Methyl 1-Boc-piperazine-2-carboxylate 2756818, apiperazines compound, is more and more widely used in various fields.

129799-15-1, Methyl 1-Boc-piperazine-2-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 1-tert-butyl 2-methyl piperazine-1,2-dicarboxylate (500 mg, 2.04 mmol) and an ammonia methanol solution (7 M, 10mL) in a 100 mL of sealing tube was stirred at 60 for 72 h and concentratedto give the title compound as a white solid (200 mg, 42) . 1H NMR (400 MHz, CD3OD): delta ppm 5.47-5.76, 6.11-6.36 (m, 0.5H, 0.5H) , 4.51-4.68 (m, 1H) , 3.44-3.57(m, 1H) , 2.89-3.02 (m, 2H) , 2.66-2.80 (m, 2H) , 1.47 (m, 9H) and MS-ESI:m/z 230.30 [M+H] +., 129799-15-1

129799-15-1 Methyl 1-Boc-piperazine-2-carboxylate 2756818, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LIU, Bing; YU, Tianzhu; ZHANG, Xiangyu; ZHANG, Shiguo; ZHANG, Jiancun; CHENG, Changchung; (426 pag.)WO2016/34134; (2016); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Brief introduction of (S)-tert-Butyl 2-methylpiperazine-1-carboxylate

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

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.

2,3,7-Trichloropyrido[2,3-b]pyrazine (200.0 mg, 0.85 mmol) and TEA (1180.0 muL, 8.53 mmol) were dissolved in DCM (8.5 mL), and (S)-tert-butyl 2-methylpiperazin-1-carboxylate (187.8 mg, 0.94 mmol) diluted in DCM (0.5 mL) was slowly added thereto at -20 C. The reaction mixture was stirred at -20 C. for 12 hours, and it was poured into saturated NH4Cl aqueous solution and extracted with DCM (30.0 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and then distilled under reduced pressure. The residue was purified by column chromatography (EtOAc:n-Hex=30:70) on silica. The fractions containing the product were collected and evaporated to obtain yellow solid compound of (S)-tert-butyl 4-(2,7-dichloropyrido[2,3-b]pyrazin-3-yl)-2-methylpiperazin-1-carboxylate (233.0 mg, 67%). [0544] LCMS ESI(+): 398 (M+1), 400 (M+3) [0545] 1H-NMR (300 MHz, DMSO-d6); delta: 8.96 (d, 1H, J=2.7 Hz), 8.54 (d, 1H, J=2.7 Hz), 4.30 (m, 1H), 4.09 (m, 2H), 3.88 (m, 1H), 3.20 (m, 2H), 3.04 (m, 1H), 1.43 (s, 9H), 1.24 (d, 3H, J=6.6 Hz)

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

Reference£º
Patent; C&C RESEARCH LABORATORIES; Ho, Pil Su; Yoon, Dong Oh; Han, Sun Young; Lee, Won Il; Kim, Jung Sook; Park, Woul Seong; Ahn, Sung Oh; Kim, Hye Jung; US2014/315888; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of (R)-1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate

As the paragraph descriping shows that 438631-77-7 is playing an increasingly important role.

438631-77-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.438631-77-7,(R)-1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate,as a common compound, the synthetic route is as follows.

To a de-gassed solution of 78 THF (325 ml) and 56 DIPEA (12.74 ml, 73.14 mmol) under a nitrogen atmosphere was added 113 7-bromo-4,6-dichloro-8-fluoro-3-nitroquinoline (26.59 g, 66.49 mmol) and 272 1-(tert-butyl) 3-methyl (R)-piperazine-1,3-dicarboxylate (17.05 g, 69.81 mmol). The resultant brown solution was heated at 61 C. (internal temperature) under a nitrogen atmosphere for 18 hours. Additional DIPEA (5.8 ml, 33.24 mmol) and 1-(tert-butyl) 3-methyl (R)-piperazine-1,3-dicarboxylate (8.12 g, 33.24 mmol) was then added and the resultant reaction mixture was heated at 61 C. (internal) for 4 hours. The reaction mixture was concentrated in vacuo, and the crude product was purified by flash silica chromatography, elution gradient 0 to 50% 57 ethyl acetate in 58 heptane. Pure fractions were evaporated to dryness to afford 273 1-tert-butyl 3-methyl (3R)-4-(7-bromo-6-chloro-8-fluoro-3-nitroquinolin-4-yl)piperazine-1,3-dicarboxylate (32.1 g, 88%) as an orange solid. 1H NMR (400 MHz, DMSO, 30 C.) 1.45 (9H, s), 2.52-2.53 (1H, m), 3.29-3.34 (1H, m), 3.56 (3H, s), 3.61-3.77 (2H, m), 3.78-3.93 (1H, m), 4.04-4.21 (1H, m), 4.33-4.4 (1H, m), 8.36 (1H, d), 9.16 (1H, s). m/z: ES+ [M+H]+ 547. 97% ee.

As the paragraph descriping shows that 438631-77-7 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

New learning discoveries about 1-Cbz-Piperazine

As the paragraph descriping shows that 31166-44-6 is playing an increasingly important role.

31166-44-6, 1-Cbz-Piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 250 ml round bottomed flask 5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde (Intermediate B37) (780 mg, 2.60 mmol) was dissolved in 30 ml of DCM then acetic acid (0.446 ml, 7.79 mmol) and benzyl piperazine-1-carboxylate (1.503 ml, 7.79 mmol) were added. After few minutes sodium triacetoxyhydroborate (2.75 g, 12.99 mmol) was added and the mixture was stirred at r.t. The mixture was poured into 100 ml of DCM and 100 NaHCO3 sat. sol. then phases were separated and the organic one was concentrated to dryness to leave a brown oil that was immediately purified by chromatography eluting with HexaneEtOAc mixtures to leave the title compound (903 mg, 1.790 mmol, 68.9percent yield) as a yellow oil.UPLC-MS: 0.79 min, 505.12 [M+H]+, method 9, 31166-44-6

As the paragraph descriping shows that 31166-44-6 is playing an increasingly important role.

Reference£º
Patent; CHIESI FARMACEUTICI S.p.A.; Biagetti, Matteo; Capelli, Anna Maria; Accetta, Alessandro; Carzaniga, Laura; US2015/166549; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of 393781-70-9

As the paragraph descriping shows that 393781-70-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.393781-70-9,(R)-1-Boc-2-Ethylpiperazine,as a common compound, the synthetic route is as follows.

Step A: To a solution of (R)-tert-butyl 2-ethylpiperazine-l-carboxylate (0.208 g, 0.971 mmol, Eq: 1.00) and triethylamine (0.135 ml, 0.971 mmol, Eq: 1.00) in DMF (2ml) was added methyl 2,6- dichloronicotinate (0.200 g, 0.971 mmol, Eq: 1.00) and the reaction mixture stirred at 30C for 4.5 hrs. The reaction mixture was diluted with EtOAc and washed with water and brine, the organic phase was dried over Na2S04 and the solvent evaporated. The crude was purified by column chromatography (Si02, EtOAc/Heptane, 1/4) to give 160 mg (43%) of tert-butyl (2R)-4- (6-chloro-5-methoxycarbonyl-2-pyridyl)-2-ethyl-piperazine-l-carboxylate as a white solid. MS (m/e): 384.2 (M+H+)., 393781-70-9

As the paragraph descriping shows that 393781-70-9 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GREEN, Luke; PINARD, Emmanuel; RATNI, Hasane; WILLIAMSON, Patrick; (95 pag.)WO2015/197503; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of tert-Butyl 3,5-dimethylpiperazine-1-carboxylate

639068-43-2 tert-Butyl 3,5-dimethylpiperazine-1-carboxylate 22219990, apiperazines compound, is more and more widely used in various fields.

639068-43-2, tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred solution of compound 13a-b, 17a-b (1.0 mmol) inCH3CN (20 mL) were added N-Boc-piperazine (180.9 mg,0.9 mmol), K2CO3 (205.9 mg, 1.5 mmol), KI (166.0 mg, 1.0 mmol)and 18-crown-6 (26.4 mg, 0.1 mmol) at room temperature. Themixture was stirred overnight at 80 C and filtered. The filtrate wasdiluted by DCM and washed by brine. The organic layer was concentrated for next step. To a stirred solution of the abovecompounds in DCM (20 mL) was added TFA (3 mL) at room temperature.The mixture was stirred for 3e4 h and concentrated toafford the crude products 15a-o and 19a-f in a yield of 35%e42%. Toa stirred solution of above crudes in anhydrous MeOH (10 mL) wasadded BTZ core compound 11 (403.2 mg, 1.0 mmol) and Et3N(0.2 mL, 1.5 mmolj) at room temperature. The mixture was stirredfor 1e3 h at 40 C and concentrated. The residue was purified bysilica gel column (DCM: MeOH 20: 1) to give 1a-f and 2a-e (25%e41% for two steps)., 639068-43-2

639068-43-2 tert-Butyl 3,5-dimethylpiperazine-1-carboxylate 22219990, apiperazines compound, is more and more widely used in various fields.

Reference£º
Article; Wang, Apeng; Lv, Kai; Tao, Zeyu; Gu, Jian; Fu, Lei; Liu, Mingliang; Wan, Baojie; Franzblau, Scott G.; Ma, Chao; Ma, Xican; Han, Bing; Wang, Aoyu; Xu, Shijie; Lu, Yu; European Journal of Medicinal Chemistry; vol. 181; (2019);,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics