Heterocyclic Building Blocks-piperazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.485841-52-9,(S)-1,2-Dimethylpiperazine,as a common compound, the synthetic route is as follows.,485841-52-9

General procedure: To a solution of 53 (0.1 mmol, 1.0 eq.) in EtOH (2 mL) was addedEt3N (10.0 eq.) and corresponding amine (5.0 eq.). The reactionwasstirred at 85 C overnight, and then quenched with saturatedNaHCO3 aqueous solution. The aqueous layer was extracted withdichloromethane. The organic layer was dried over Na2SO4 andconcentrated. The residue was purified by silica gel column chromatography(dichloromethane/methanol 100/1) to give thedesired product.

The synthetic route of 485841-52-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Du, Qian; Fu, Chunyan; Ge, Wenxiang; He, Sudan; Li, Zhanhui; Luo, Lusong; Ma, Haikuo; Sun, Xiaotian; Tian, Sheng; Wang, Xu; Wang, Yujie; Zhang, Xiaohu; Zhang, Yi; Zheng, Jiyue; Zhu, Fang; European Journal of Medicinal Chemistry; (2019);,
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630125-91-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.630125-91-6,4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline,as a common compound, the synthetic route is as follows.

To a solution of 100 mg (0.69 mmol) of 3-ethynyl benzoic acid in 5 mL of dry N,N-dimethylformamide, 164 mg (0.57 mmol) of 4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)aniline (prepared as described in J. Med. Chem., (2010) 53, 4701-4719) 242 mg (0.75 mmol) of TBTU and 0.14 mL (0.82 mmol) of DIPEA were added consecutively. After 15 h under stirring at room temperature the mixture was poured into aqueous NaHC03 and extracted twice with ethylacetate. The organic phase was then washed with brine, dried over Na2S04 and evaporated to dryness. A flash- chromatography on silica gel (DCM-MeOH-NH3 7N in methanol 9/1/0.04), afforded 149 mg of the title compound (63%). 1H NMR (600 MHz, DMSO-d6) delta ppm 0.99 (t, J=7.14 Hz, 3 H) 2.19 – 2.46 (m, 10 H) 3.57 (s, 3 H) 6.61 (br. s., 2 H) 7.60 (t, J=7.88 Hz, 1 H) 7.64 (d, J=2.20 Hz, 1 H) 7.72 (d, J=8.61 Hz, 1 H) 7.80 (dt, J=7.83, 1.21 Hz, 1 H) 7.91 – 7.98 (m, 1 H) 8.05 (dd, J=8.52, 1.92 Hz, 1 H) 8.12 (s, 1 H) 8.16 (t, J=1.47 Hz, 1 H) 8.21 (d, J=2.20 Hz, 1 H) 10.59 (s, 1 H) 12.08 (br. s., 1 H) HRMS (ESI) calcd for C29H28N7OF3 [M+H]+ 548.2380, found 548.2392.

As the paragraph descriping shows that 630125-91-6 is playing an increasingly important role.

Reference£º
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; ANGIOLINI, Mauro; BUFFA, Laura; MENICHINCHERI, Maria; MOTTO, Ilaria; POLUCCI, Paolo; TRAQUANDI, Gabriella; ZUCCOTTO, Fabio; WO2014/184069; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.169447-86-3,(S)-tert-Butyl 2-benzylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of 122 and 123 (-0.216 mmol) in dioxane (3 ml_) was added (S)~N-Boc-2-benzylpiperazine (0.07 g, 0.254 mmol) and diisopropylethylamine (0.077 ml_, 0.443 mmol). The reaction mixture was heated at 600C for 1 hour. The organic solvent was evaporated under reduced pressure. The crude product mixture was purified by RP-HPLC to yield 3-(3-methylindazol-5-yl)-5-[(S)-4-Boc-3-benzylpiperazin-1-yl]- [1 ,2,4]triazine 124 (0.012 g, 0.025 mmol) and 6-chloro-3-(3-methylindazol-5- yl) )-5-[(S)-4-Boc-3-benzylpiperazin-1-yl]-[1 ,2,4]triazine 125 (0.02 g, 0.038 mmol).

169447-86-3, The synthetic route of 169447-86-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SCHERING CORPORATION; WO2006/81230; (2006); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.373608-48-1,tert-Butyl 4-(3-aminopropyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of 4-(4-chloro-1,6-naphthyridin-2-yl)-N,N-diethylbenzamide (300 mg, 0.88 mmol) in DMF (5 mL) were added tert-butyl 4-(3-aminopropyl)piperazine-1-carboxylate (321 mg, 1.32 mmol) and K2C03 (240 mg, 1.76 mmol). After stirred at 100C overnight, the reaction mixture was quenched with water (5 mL), and extracted with DCM (10 mL x 3). The organic layer was washed with water (10 mL x 3) and brine (10 mL), dried over Na2SO4, concentrated and purified by prep-HPLC to afford tert-butyl 4-(3 -((2-(4-(diethylcarbamoyl)phenyl)- 1 ,6-naphthyridin-4-yl)amino)propyl)piperazine- 1- carboxylate (300 mg, 62%) as yellow solid. HPLC/UV purity: 100%; LC-MS (ESI): 547.2 (M + 1)., 373608-48-1

373608-48-1 tert-Butyl 4-(3-aminopropyl)piperazine-1-carboxylate 17750945, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; PINKERTON, Anthony B.; ARDECKY, Robert J.; ZOU, Jiwen; (256 pag.)WO2018/204176; (2018); A1;,
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304897-49-2, tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2 Synthesis of Compound 5 tert-Butyl 4-[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl-1-piperazinecarboxylate (5). To compound 3 (0.68 g, 2.1 mmol) in ethyl acetate (100 mL) was added 10% Pd/C (0.1 g), and the reaction mixture was hydrogenated for 2 h under a pressure of 60 lb/inch2. The product was filtered, and solvent was removed in vacuo to afford amine 4 (0.6 g, 97% yield). Without further purification, to amine 4 (0.6 g, 2.06 mmol) dissolved in acetonitrile (90 mL) was added cis-4,7,10,13,16,19-docosahexenoic acid (DHA, 0.67 g, 2.0 mmol), 2-(1-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU, 0.94 g, 2.5 mmol), and N,N-diisopropylethylamine (2.1 mL). The reaction mixture was stirred overnight. Solvent was removed in vacuo, and the product was purified by column chromatography, eluding with ethyl acetate to afford 5 as an oil (0.91 g, 73% yield). 1H NMR (DMSO-d6): 9.84 (s, 1H, NH), 7.53-7.51 (d, 2H, J=8.80 Hz, Ar-H), 7.19-7.17 (d, 2H, J=8.40 Hz, Ar-H), 5.35-5.31 (m, 12H, CH=CH), 3.40 (s, 2H, CH2), 3.29 (brs, 4H, 2*CH2), 2.83-2.75 (m, 10H, 5*CH2), 2.35 (brs, 4H, 2*CH2), 2.27 (t, 4H, J=4.80 Hz, 2*CH2), 2.04-2.00 (m, 2H, CH2), 1.38 (s, 9H, 3*CH3), 0.91 (t, 3H, J=7.20 Hz, CH3). Anal. (C38H55N3O3.4.1H2O) C, H, N

304897-49-2, The synthetic route of 304897-49-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wang, Yuqiang; US2004/34033; (2004); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.694499-26-8,4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline,as a common compound, the synthetic route is as follows.

694499-26-8, Step 1: Preparation of N-(3-iodo-4-methylphenyl)-N’-[4-((4-methylpiperazin-1-yl)methyl)-3-trifluoromethylphenyl]urea Triphosgene (1.04 g, 3.5 mmol) and ClCH2CH2Cl (20 ml) were added into a 100 ml round-bottomed flask, and stirred at room temperature until triphosgene was completely dissolved and the system appears colorless and transparent. The reaction system was placed in an ice-salt bath and stirred, 3-iodo-4-methylaniline (1.64 g, 7 mmol) in ClCH2CH2Cl solution (20 ml) was slowly added dropwise, and the system appears yellow milky. After the addition was complete, the mixture was stirred at room temperature for 4 hours. Et3N (1.43 g, 14 mmol) was added and stirred at room temperature for 0.5 hour. 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylaniline (1.87 g, 7 mmol) was added and stirred at room temperature for 16 hours. The volatiles were removed by distillation under reduced pressure, and the residue was extracted with ethyl acetate (30 ml x 3) and H2O (30 ml). The organic phases were combined, dried over anhydrous Na2SO4, concentrated, and purified by column chromatography, to give a yellow solid. ESI-MS m/z: [M+H]+= 533.2, calculated: 533.3.

As the paragraph descriping shows that 694499-26-8 is playing an increasingly important role.

Reference£º
Patent; Nanjing Sanhome Pharmaceutical Co., Ltd.; WANG, Yong; ZHAO, Liwen; ZHANG, Di; WU, Feng; BI, Sheng; GAO, Yiping; CHEN, Hongbin; CHEN, Hongyan; ZHANG, Cang; NAN, Yang; LIU, Yang; EP2927232; (2015); A1;,
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5317-33-9,5317-33-9, 3-(4-Methylpiperazin-1-yl)propan-1-ol is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 6-substituted pyridazinone 9 (0.5 mmol) in DMF (10 mL) was added Cs2CO3 (0.55 mmol). An appropriately substituted nitro benzyl chloride (0.52 mmol) was added and the resulting mixture was stirred at 40-50 C for 3 h, the solvent was removed under reduced pressure and the residue was dissolved in EtOAc (30 mL), which was then washed with brine (3 ¡Á 10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product, 2-nitrobenzyl-6-substituted-pyridazin-3(2H)-one (10), was used in the next step without further purification. To a solution of 10 in 95 % ethanol (50 mL) was added acetic acid (10 mmol) followed by slow addition of iron powder (2 mmol). The resulting mixture was stirred for 5 h at 100 C. The mixture was then filtered through celite and the filter cake was washed with 95 % ethanol (3 ¡Á 15 mL). The combined ethanol filtrates were evaporated in vacuo and the residue was re-dissolved in ethyl acetate (30 mL). The organic layer was washed with brine (3 ¡Á 10 mL) and 2 M NaOH (10 mL) sequentially. The organic layer was dried over anhydrous Na2SO4, evaporated in vacuo to afford 2-aminobenzyl-6-substituted-pyridazin-3(2H)-one (11) as a yellow solid, which was used without further purification. To a stirred solution of 11 and triphosgene (1 mmol) in dry dichloromethane (5 mL) was added triethylamine (2 mmol) under nitrogen atmosphere. A solution of the corresponding alcohol (1 mmol) in dichloromethane (5 mL) was added 5-10 min later and the mixture was stirred at room temperature overnight, diluted with dichloromethane (15 mL) and washed with water (3 ¡Á 20 mL). The organic phases were separated, combined, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by using column chromatography to afford the corresponding product.

As the paragraph descriping shows that 5317-33-9 is playing an increasingly important role.

Reference£º
Article; Xing, Weiqiang; Ai, Jing; Jin, Shiyu; Shi, Zhangxing; Peng, Xia; Wang, Lang; Ji, Yinchun; Lu, Dong; Liu, Yang; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 302 – 312;,
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1030377-21-9, (S)-1-Boc-2-(Hydroxymethyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A vial was charged with 5-amino-3,6-dichloro-l ,2,4-triazine (589.6 mg, 3.57 mmol), triethylamine (1.5 mL, 10.76 mmol), (S)-tert-butyl 2-(hydroxymethyl)piperazine-l- carboxylate (890 mg, 3.99 mmol) in dioxane (12 mL). The mixture was heated at 95 C for 1.5 h using microwave. The mixture was cooled to room temperature and transferred into a flask with dichloromethane, concentrated to remove the solvents. The residue was mixed with saturated potassium carbonate, extracted with dichloromethane (3 x 40 mL). The combined organic solution was dried over anhydrous sodium sulfate, concentrated. The residue was separated with flash column chromatography on silica gel using 1-5% methanol in dichloromethane to afford the product (955.7 mg) in 78%. NMR (500 MHz, Chloroform- d) delta 5.30 (s, 2H), 4.69 (br, 1H), 4.45 (d, J= 12.3 Hz, 1H), 4.21 (s, IH), 3.88 (s, 1H), 3.52 (s, I 1H), 3.42 (s, 1H), 3.13 (d, J = 14.2 Hz, lH), 3.02 (t, J = 12.0 Hz, 1H), 2.93 (s, 1H), 1.43 (s, 9H). MS for C3H21CIN6O3: 345.2 (MH+)., 1030377-21-9

The synthetic route of 1030377-21-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NEKTAR THERAPEUTICS (INDIA) PVT. LTD.; NEKTAR THERAPEUTICS; SHARMA, PANKAJ; KHATRI, VIJAY KUMAR; GU, XUYUAN; SONG, YUAN; SHEN, MICHAEL LIXIN; SAUTHIER, JENNIFER RIGGS; ANAND, NEEL K.; KOZLOWSKI, ANTONI; ODINECS, ALEKSANDRS; RILEY, TIMOTHY A.; REN, ZHONGXU; MU. YONGQI; SHEN, XIAOMING; YUAN. XUEJUN; AURRECOECHEA, NATALIA; O’MAHONY, DONOGH JOHN ROGER; WO2015/92819; (2015); A2;,
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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, (b) (2S,5R)-4-[5-(4-Bromo-3-trifluoromethoxy-phenylcarbamoyl)-pyridin-2-yl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester The product of the previous step (3.86 g, 10.2 mmol) (2S,5R)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (2.62 g, 12.2 mmol) and N,N-diisopropylethylamine (5.32 mL, 30.5) was dissolved in DMSO (12 mL). The reaction mixture heated at 120 C for 3 h, diluted with EtOAc (100 mL), washed with water, and saturated NH4Cl, water, and brine. The reaction mixture was evaporated to about 40% volume and 3 M HCl in cyclopentyl methyl ether (4.24 mL, 12.7 mmol) was added slowly. Seeds from a previous run at smaller scale were added and the reaction mixture was stirred for 2 days and filtered to provide the HCl salt of the title intermediate (5.15 g, 83 % yield). HPLC method C: Retention time = 21.1 min

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;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.122833-04-9,2-Methoxy-4-(4-methylpiperazin-1-yl)aniline,as a common compound, the synthetic route is as follows.

General procedure: A mixture of 5a(210 mg, 0.690 mmol) and MsOH (0.13 mL, 2.00 mmol) in EtOH (3 mL) was stirred at room temperature for 15 min. To this mixture was added 13a (170 mg, 0.543 mmol), and the reaction mixture was stirred at 100C for 2 h. After the mixture was cooled to room temperature, water and saturated aqueous NaHCO3 solution were added. The resulting slurry was extracted with CHCl3, and the organic layer was dried overNa2SO4, then concentrated in vacuo. The residue was purifiedby silica gel column chromatography (CHCl3/MeOH/28%aqueous NH3=50 : 1 : 0.1 to 30 : 1 : 0.1) to give 14a (180 mg,57%)., 122833-04-9

122833-04-9 2-Methoxy-4-(4-methylpiperazin-1-yl)aniline 20136253, apiperazines compound, is more and more widely used in various fields.

Reference£º
Article; Iikubo, Kazuhiko; Kondoh, Yutaka; Shimada, Itsuro; Matsuya, Takahiro; Mori, Kenichi; Ueno, Yoko; Okada, Minoru; Chemical and Pharmaceutical Bulletin; vol. 66; 3; (2018); p. 251 – 262;,
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