Heterocyclic Building Blocks-piperazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.934-98-5,2-(4-Methylpiperazin-1-yl)ethanamine,as a common compound, the synthetic route is as follows.

Maleic anhydride (501.9 mg, 5.11 mmol) was dissolved in CHC13 (25 mL) and 2-(4- methylpiperazin-l-yl)ethan-l -amine (767 mu^, 5.11 mmol) was then added. The reaction was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the crude solid was resuspended in acetic anhydride (25 mL). To the reaction was then added sodium acetate (250 mg). The reaction was heated to reflux under N2 for 3 hours. After reflux, the reaction was cooled to room temperature and washed with hexanes to obtain 3 (crude) as a dark brown/black oil. MS: m/z (M+l) +: 224.28, 934-98-5

As the paragraph descriping shows that 934-98-5 is playing an increasingly important role.

Reference£º
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James E.; QI, Jun; FEDERATION, Alexander; JACOBSON, Zoe; VARCA, Anthony; (125 pag.)WO2018/58029; (2018); A1;,
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120737-59-9, tert-Butyl 3-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 135 1-fluoro-4-nitrobenzene (5.0 g, 35.46 mmol, 1.0 eq) and 248 tert-butyl 3-methylpiperazine-1-carboxylate (7.09 g, 35.46 mmol, 1.0 eq) in 95 DMSO (40 mL) was added 64 K2CO3 (9.78 g, 70.92 mmol, 2.0 eq). The reaction mixture was heated at 120¡ã C. for 16 h. Progress of the reaction was monitored by LCMS. Upon the consumption of starting material, mixture was diluted with water (100 mL) and extracted with ethyl acetate (200 mL¡Á2). Combined organic layer was washed with water (50 mL¡Á3), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Crude residue was purified by flash chromatography using 19 ethyl acetate: 20 hexane as eluents to obtain 249 tert-butyl 3-methyl-4-(4-nitrophenyl)piperazine-1-carboxylate (5.5 g, 48.67percent). (0378) LCMS: 322 [M+1]+, 120737-59-9

The synthetic route of 120737-59-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; KUMAR, Varun; (360 pag.)US2019/106436; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34770-60-0,4-Methylpiperazin-2-one,as a common compound, the synthetic route is as follows.

To a solution of (5R)-9-[2-(3-bromophenyl)-3,3,3-trifluoro-2-methoxypropanoyl]-5-(4- fluorophenyl)-3,9-diazaspiro[5.5]undecan-2-one (Example 1 14) (100.0 mg, 179 pmol) and 4- methylpiperazin-2-one (CAS-RN: 34770-60-0) (41 .0 mg, 359 pmol) in 1 ,4-dioxane (1 mL) was added caesiumcarbonat (146 mg, 449 pmol), Dipalladium- tris(dibenzylideneacetone)chloroform complex (CAS-RN: 52522-40-4) (9.29 mg, 8.97 pmol) and 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, CAS-RN: 161265-03-8). The mixture was stirred at 900 for 8 h. The reac tion mixture was diluted with water and extracted with dichloromethane. The combined organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified via preparative HPLC (method 6) to give the title compound 9.60 mg (90 % purity, 8 % yield).LC-MS (Method): Rt= 1 .04 min; MS (ESIpos): m/z = 591 [M+H]+1H-NMR (400 MHz, DMSO-d6) d [ppm]: 0.243 (0.68), 0.266 (0.45), 0.540 (0.91 ), 0.570 (0.76), 1 .022 (0.74), 1 .056 (1 .20), 1 .145 (0.52), 1 .170 (0.58), 1.279 (1.50), 1 .432 (0.95), 1.463 (0.82), 1 .646 (0.41 ), 1 .898 (0.99), 1 .942 (1 .30), 2.169 (1 .55), 2.219 (2.82), 2.235 (2.31 ), 2.272 (10.52), 2.293 (16.00), 2.331 (0.85), 2.338 (0.64), 2.518 (4.14), 2.523 (2.99), 2.539 (2.14), 2.699 (1 .1 1 ), 2.712 (1 .94), 2.728 (3.32), 2.744 (4.02), 2.757 (2.47), 2.777 (1.05), 2.793 (1 .83), 2.810 (1 .03),2.844 (0.66), 2.876 (1 .09), 2.907 (0.62), 3.027 (0.60), 3.062 (1.38), 3.080 (1 .48), 3.094 (1 .34),3.1 14 (6.29), 3.140 (9.75), 3.240 (2.06), 3.372 (6.95), 3.577 (10.91 ), 3.595 (2.47), 3.606 (2.31 ), 3.623 (1 .30), 3.662 (0.85), 3.676 (1.51 ), 3.690 (1 .67), 3.704 (1.44), 3.714 (1 .15), 3.726 (0.52),3.970 (0.56), 4.004 (0.52), 4.168 (0.85), 4.200 (0.80), 6.944 (1.96), 6.958 (2.39), 6.966 (2.89),6.980 (2.47), 7.035 (1 .05), 7.054 (1.13), 7.1 19 (2.68), 7.134 (2.47), 7.141 (4.97), 7.155 (3.90),7.162 (2.68), 7.177 (1 .96), 7.243 (1.05), 7.266 (2.66), 7.280 (2.17), 7.288 (1 .84), 7.296 (2.25),7.302 (1.88), 7.316 (4.17), 7.336 (1.55), 7.403 (0.99), 7.425 (1.61 ), 7.445 (2.83), 7.466 (1 .92),7.486 (2.41 ), 7.505 (2.66), 7.524 (1.65), 7.565 (0.41 ), 7.573 (0.43), 7.606 (3.05), 7.633 (2.04)., 34770-60-0

The synthetic route of 34770-60-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; BUCHGRABER, Philipp; AIGUABELLA FONT, Nuria; WITTROCK, Sven; HEINRICH, Tobias; BRAeUER, Nico; KUHNKE, Lara, Patricia; LANGE, Martin; BADER, Benjamin; PRECHTL, Stefan; LIENAU, Philip; KOPITZ, Charlotte, Christine; NOWAK-REPPEL, Katrin; POTZE, Lisette; STEUBER, Holger; (754 pag.)WO2020/48831; (2020); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.112257-24-6,1-Boc-3-Carbamoylpiperazine,as a common compound, the synthetic route is as follows.

Step 1 4-(t-butoxycarbonyl)-1-methylpiperazine-2-carboxamide A solution of 6.00 g of 4-(t-butoxycarbonyl)piperazine-2-carboxamide and 3.28 g of a 37% aqueous formaldehyde solution in 60 ml of methanol was ice-cooled, and 16.66 g of sodium triacetoxyborohydride was added, followed by stirring at room temperature for 24 hours after removing an ice bath. The reaction solution was again ice-cooled, 3.28 g of a 37% aqueous formaldehyde solution and 16.66 g of sodium triacetoxyborohydride were added thereto. After stirring at room temperature for 16 hours, the reaction solution was diluted with ice water, alkalified with an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate three times. The organic layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 5.42 g of the objective compound as colorless crystals. Melting point: 137-138C, 112257-24-6

The synthetic route of 112257-24-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nippon Shinyaku Co., Ltd.; EP1702917; (2006); A1;,
Piperazine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.21655-48-1,cis-2,6-Dimethylpiperazine,as a common compound, the synthetic route is as follows.

A Schlenk flask backfilled with N2 was charged with cw-2,6-dimethylpiperazine (0.11 g, 0.96 mmol), NaO-i-Bu (0.17 g, 1.8 mmol, (rac)-BINAP (8 mg, 0.01 mmol), Pd2(dba)3 (8 mg, 0.009 mmol), and degassed toluene (4 mL). The 2-bromotoluene (0.15 g, 0.88 mmol) was then added, and the mixture was heated under N2 at 110 ¡ãC for 24 h, cooled to rt, diluted with CH2CI2, filtered over Celite, and concentrated. The crude mixture was purified by chromatography on SiO2 (CH2Cl2 MeOH 95:5) to give the product as clear, yellow oil (140 mg, 78percent): NMR (500 MHz, CDCI3) delta 7.19-7.15 (m, 2 H), 7.02-6.98 (m, 2 H), 3.13-3.10 (m, 2 H), 3.01 (d, 7 = 10.5 Hz, 2 H), 2.35-2.31 (m, 5 H), 6 H)., 21655-48-1

The synthetic route of 21655-48-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; SKODA, Erin, M.; WANG, Zhou; WO2015/42297; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.303-26-4,1-((4-Chlorophenyl)(phenyl)methyl)piperazine,as a common compound, the synthetic route is as follows.

Example 12 : Preparation of N-(4-methylbenzyl)-4-oxo-4-((4-chlorobenzhydryl)piperazin-l-yl)butanamide; [251][252] 0.5 mmol of 3-(4-methylbenzylcarbamoyl)-propanoic acid prepared in PreparativeExample 7, 0.55 mmol of l-(4-chlorobenzhydryl)piperazine, and benzotriazol- 1-yloxytripyrrolidino phosphonium hexafluorophosphate (PyBOP) were added to 3 mL of dimethylformamide (DMF) to dissolve. Then, 1.0 mmol ofN,N-diisopropylethylamine (DIEA) was added thereto, and stirred at room temperature for 16 hours. 20 mL of 10% HCl was put into the reaction solution, and extracted with 30 mL of EtOAc. The organic layer was washed with 20 mL of 10% HCl, and then washed with 20 mL of a saturated NaHCO solution twice and with 20 mL of a saturated NaCl solution twice. The organic layer was collected, dried over anhydrous MgSO , and filtered under reduced pressure. The organic solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography with a mixed solvent of EtOAc and methanol (20:1), so as to obtain the title compound (light yellow solid, yield: 60%).[253] mp 74.5-80.30C;[254] 1U NMR (CDCl 3 ) delta 7.37-7.34 (m, 4CH), 7.32-7.13 (m, 5CH), 7.15-7.11 (t, J=4.4Hz, CH ), 3.46 (t, J=4.4Hz, CH ), 2.64 (t, J=6.4Hz, CH ), 2.53 (t, J=6.4Hz, CH ), 2.36-2.32 (m, 2CH2), 2.31(s, CH3);[255] HR-FABMS Calcd for C 29 H 33 ClN 3 O 2 : (M++l): 490.2261, Found: 490.2249., 303-26-4

The synthetic route of 303-26-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PARK CHOO, Hea-Young; WO2007/142431; (2007); A1;,
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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.

Bromobenzene (125 mg, 0.8 mmol), 1-tert-butyl 3-methyl (3R)-piperazine-1,3-dicarboxylate (213.94 mg, 0.88 mmol), Pd2(dba)3.CHCl3 (8.24 mg, 0.01 mmol), RuPhos (9.29 mg, 0.02 mmol) and Cs2CO3 (324.24 mg, 1 mmol) were suspended in anhydrous toluene (2.5 ml). The sealed reaction was heated at 110 C. for 18 h. The reaction was partitioned between DCM (5 ml) and water (5 ml) then the organics were separated and concentrated in vacuo. The residue was purified via flash column chromatography using a gradient of 0% to 100% EtOAc in heptane then 0% to 100% MeOH in EtOAc. Fractions containing product were combined and concentrated in vacuo to yield the title compound as a yellow glassy solid (51 mg, 13%). LCMS Method 2-Tr=1.21 min (ES+) (M+H+) 321.0., 438631-77-7

The synthetic route of 438631-77-7 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; (519 pag.)US2018/127370; (2018); A1;,
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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 suspension of triphosgene (17.2 mg, 0.058 mmol) and Na2C03 (37 mg, 0.348 mmol) in DCM (2 ml), kept atooc under argon, 4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (50 mg, 0.17 4 mmol) was added.The reaction was monitored by HPLC (following the formation of 4-ethyl-piperazine-1-carboxylic acid [4-(4-ethyl-5 piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-amide by treating a sample of the reaction mixture with Nethylpiperazine).After 1 h a solution of 2-[2-amino-5-(3-amino-phenylethynyl)-pyrimidin-4-yl]-1-methyl-1 ,5,6, 7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (1 04 mg, 0.226 mmol) in DMA (1.5 ml) was added and the reaction was letunder stirring overnight. The mixture was diluted with DCM, washed with water (3 x 10 ml), dried over anhydrousNa2S04 and taken to dryness under vacuum. Purification by flash column chromatography (DCM/MeOH 95/5)10 afforded the product as yellow solid (70 mg, 52%).1H NMR (401 MHz, DMSO-dG) o ppm 0.97 (t, J=7.20 Hz, 3 H) 1.45 (s, 9 H) 2.23- 2.45 (m, 10 H) 3.00 (t, J=6.3 Hz, 2H) 3.51 (s, 2 H) 3.84 (s, 3 H) 4.00 (t, J=6.16 Hz, 2 H) 7.06 (d, J=7.69 Hz, 1 H) 7.11 (s, 2 H) 7.25-7.31 (m, 1 H) 7.43(d, J=8.06 Hz, 1 H) 7.49 (s, 1 H) 7.56- 7.65 (m, 2 H) 7.72 (t, J=1.71 Hz, 1 H) 8.01 (d, J=1.71 Hz, 1 H) 8.50 (s, 1 H),10.00 (bs, 1 H), 10.19 (bs, 1 H).

630125-91-6, 630125-91-6 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline 59134564, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; MENICHINCHERI, Maria; ANGIOLINI, Mauro; BERTRAND, Jay Aaron; CARUSO, Michele; POLUCCI, Paolo; QUARTIERI, Francesca; SALOM, Barbara; SALSA, Matteo; ZUCCOTTO, Fabio; WO2014/72220; (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.393781-71-0,1-Boc-2-Ethylpiperazine,as a common compound, the synthetic route is as follows.

To a solution of 1-(6-chloro-3-pyridyl)ethanone (4.00 g, 24.9 mmol; CAS36357-38-7) in ACN (8 mL) was added DIPEA (9.67 g, 74.8 mmol) and (¡À)-tert-butyl 2-ethylpiperazine-1-carboxylate (6.41 g, 29.9 mmol; CAS393781-71-0). The reaction mixture was stirred at 85 C. for 12 hours. On completion, the reaction mixture was concentrated in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate=30:1 to 5:1) to give the title compound (8.30 g, 100% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 8.75 (d, J=2.0 Hz, 1H), 8.03 (dd, J=2.4, 9.2 Hz, 1H), 6.58 (d, J=8.8 Hz, 1H), 4.34 (d, J=13.2 Hz, 1H), 4.27 (d, J=10.4 Hz, 1H), 4.13 (q, J=7.2 Hz, 1H), 4.02 (s, 1H), 3.27 (dd, J=4.0, 13.2 Hz, 1H), 3.20-3.04 (m, 2H), 2.51 (s, 3H), 1.63-1.50 (m, 2H), 1.49 (s, 9H), 0.90 (t, J=7.2 Hz, 3H)., 393781-71-0

393781-71-0 1-Boc-2-Ethylpiperazine 18004789, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34334-28-6,4-(4-Methylpiperazin-1-yl)benzonitrile,as a common compound, the synthetic route is as follows.

To a solution of 13 (1eq.) and CoCl2 6H20(2.1 eq.), NaBH4 (10 eq.) was added. The reaction mixture wasstirred for 5h and then filtered on a celite pad. The organic phase wasevaporated under reduced pressure. The yellow oil was purified by flashchromatography on silica gel (CH2Cl2:MeOH 8:2). Thedesired compound was obtained as a white solid (50%). 1H NMR (400MHz, MeOD): delta(ppm) 2.42(s, 3H); 2.74(t, J=8, 4H); 3.17(t, J=8, 4H), 4.43(s,2H); 6.89(d, J=8, 2H); 7.18(d, J=8, 2H). Anal. Calcd. for C12H19N3:C, 70.20; H, 9.33; N, 20.47; found; C, 70.10; H, 9.13; N, 20.27

34334-28-6, 34334-28-6 4-(4-Methylpiperazin-1-yl)benzonitrile 763205, apiperazines compound, is more and more widely used in various fields.

Reference£º
Article; Radi, Marco; Bernardo, Vincenzo; Vignaroli, Giulia; Brai, Annalaura; Biava, Mariangela; Schenone, Silvia; Botta, Maurizio; Tetrahedron Letters; vol. 54; 38; (2013); p. 5204 – 5206;,
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