Heterocyclic Building Blocks-piperazine

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 solution of 1-(chloro(4-fluorophenyl)methyl)-4-fluoro-2-methoxybenzene (200 mg, 0.744 mmol) in acetonitrile (5 mL) were added tert-butyl (2S,5R)-2,5- dimethylpiperazine-1-carboxylate (239 mg, 1.117 mmol) and DIPEA (0.390 mL, 2.233 mmol). The reaction mixture was heated to 80 C for 4 h. The reaction mixture was diluted with water and extracted twice with ethyl acetate (20 mL). The organic layer was separated and dried over Na2SO4 and evaporated to dryness to yield tert-butyl (2S,5R)-4- ((4-fluoro-2-methoxyphenyl)(4-fluorophenyl)methyl)-2,5-dimethylpiperazine-1- carboxylate (160 mg, 39.5 % yield) as an off-white solid; LCMS: m/z = 447.4 (M+H); rt 1.75 and 1.76 min (Diastereomer mixture). Method: Column: AQUITY UPLC BEH C18 (3.0x50mm) 1.7 ^m, Mobile phase A:10 mM ammonium acetate:acetonitrile (95:5) M. phase B: 10 mM ammonium acetate:acetonitrile (5:95), Flow: 0.7 mL/min, 548762-66-9

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

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

115619-01-7, 4-(4-Ethylpiperazin-1-yl)phenylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

48.3 1-(2,4-Dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-3-[4-(4-ethylpiperazin-1-yl)-phenylamino]-5-iodo-1,3-dihydroindol-2-one4-(4-Ethylpiperazin-1-yl)phenylamine (44 mg, 0.21 mmol) was added to a solution of 3-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5-iodo-1,3-dihydroindol-2-one (110 mg, 0.18 mmol) in dichloromethane (15 ml). The reaction mixture was agitated in a Biotage microwave vial at 120 C. for 4 hours. The reaction mixture was concentrated under reduced pressure. Purification by chromatography (silica gel, 0-8% methanol in dichloromethane) resulted in 16 mg of the title compound (11% yield).ESI-MS: 784.20 [m+H]+ 1H-NMR (500 MHz, d6-DMSO): delta [ppm] 8.15 (m, 1H); 8.05 (d, 1H); 7.85 (d, 1H); 7.75 (d, 1H); 7.50 (d, 1H); 7.30 (s, 1H), 7.10 (dd, 1H); 6.70 (d, 1H); 6.65 (s, 1H); 6.45 (d, 2H); 6.40 (d, 2H); 4.05 (m, 2H); 3.85 (s, 3H); 3.55 (s, 3H); 2.95 (bs, 4H); 2.45 (bs, 4H); 2.35 (m, 2H); 1.00 (t, 3H); 0.90 (t, 3H)., 115619-01-7

As the paragraph descriping shows that 115619-01-7 is playing an increasingly important role.

Reference：
Patent; Abbott GmbH & Co. KG; US2011/105454; (2011); 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.259808-67-8,1-Boc-3,3-Dimethylpiperazine,as a common compound, the synthetic route is as follows.

259808-67-8, To a stirred solution of amine compound 2(0.5 g, 1 eq) and aldehyde 1(0.421 g, 1.1 eq) in DCM (10 mL), sodium triacetoxyborohydride (STAB) (0.693 g, 1 .4 eq) was added. The reaction mixture was stirred at room temperature for overnight; the reaction progress was monitored by TLC and LCMS. After completion of reaction, the reaction mixture was partitioned between DCM and water. The organic layers were separated, washed with water and brine, dried over Na2504 and evaporated to get the crude product which was purified by silica gel column chromatography to afford the desired compound 3.

The synthetic route of 259808-67-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BIOMARIN PHARMACEUTICALS INC.; LUEDTKE, Gregory; BHAGWAT, Shripad; (99 pag.)WO2018/119362; (2018); A2;,
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.161357-89-7,1-(Methylsulfonyl)piperazine hydrochloride,as a common compound, the synthetic route is as follows.

A -mixture of 4,6-dichloropyrinidine (39.4 g), 1-mesylpiperazine hydrochloride (55.7 g) and triethylamine (116 ml) in ethanol (500 ml) was stirred at reflux temperature for 4 hours. The mixture was then stirred at room temperature for 12 hours. The solid, which had separated, was collected by filtration, slurry washed with ethanol (2×80 ml 160 ml) then with diethyl ether (150 ml), and dried to give 1-(6-chloropyrimidin-4-yl)4-mesylpiperazine as a cream solid (71.9 g). mp 200-202 C. [00257] NMR (d6-DMSO): 2.88 (s, 3H), 3.18 (m, 4H), 3.80 (m, 4H), 7.04 (s, 1H), 8.38 (m, 1H); m/z 277.3 (M+1)., 161357-89-7

As the paragraph descriping shows that 161357-89-7 is playing an increasingly important role.

Reference：
Patent; AstraZeneca AB; US6734184; (2004); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

170911-92-9, tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 250 mL round bottom flask was added 5 g (18.1 mmol) of crude I-f,Nitro-lH-pyrazole-3-carboxylic acid (3.1 g, 19.9 mmol)EDC · HCl 4.1 g (21.7 mmol),HOBt 2.9 g (21.7 mmol) and anhydrous DMF 50 mL,Stir at room temperature for 24 hTLC detects the disappearance of the starting material (methanol: chloroform = 1:10).The reaction solution was poured into 200 mL of ice water,Precipitation of a large number of light yellow solid, standing,Consider the yellow solid,The crude product was recrystallized from a mixed solvent of ethyl acetate and methanol to give 4.7 g of (I-g)Yield 62.4%., 170911-92-9

As the paragraph descriping shows that 170911-92-9 is playing an increasingly important role.

Reference：
Patent; China Pharmaceutical University; Lu Shuai; Wang Yue; Zhi Yanle; Yao Chao; Lu Tao; Li Baoquan; Chen Puzhou; Bao Jiyin; (27 pag.)CN107245073; (2017); A;,
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.108-49-6,2,6-Dimethylpiperazine,as a common compound, the synthetic route is as follows.

Step 1. tert-Butyl 3,5-dimethylpiperazine-1-carboxylate. To a solution of 2,6-cis-dimethylpiperazine (2.0 g, 17 mmol) in CH2Cl2 (60 ml) were sequentially added di-tert-butyl dicarbonate (3.8 g, 17 mmol) and a catalytic amount of DMAP. The reaction mixture was stirred at room temperature overnight before it was washed with water (50 ml), brine (10 ml), and extracted with CH2Cl2 (3*30 ml). The extracts were dried (MgSO4) and concentrated under reduced pressure to give product 146 as colorless oil (3.95, ~100percent).

108-49-6, As the paragraph descriping shows that 108-49-6 is playing an increasingly important role.

Reference：
Patent; Wu, Chengde; Anderson, C. Eric; Bui, Huong; Dupre, Brian; Gao, Daxin; Holland, George W.; Kassir, Jamal; Li, Wen; Wang, Junmei; US2005/54850; (2005); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

109384-27-2, 1-Methylpiperazin-2-one hydrochloride is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[Example 62] 1- [5- (1-Methyl-1H-pyrrol-3-yl) -1- (pyridin-3-yl) – 1H-pyrazole-3-carbonyl]-4-methyl-3-oxopiperazine [Show Image] [Show Image] 1-Hydroxybenzotriazole (0.132 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.378 g), triethylamine (0.630 mL), and 1-methylpiperazin-2-one hydrochloride (0.200 g) obtained from Referential Example 15 were added at room temperature to a solution of 5-(1-methylpyrrol-3-yl)-1-(pyridin-3-yl)-1H-pyrazole-3-carboxylic acid (0.242 g) obtained from Referential Example 38 in N,N-dimethylformamide (5.0 mL), and the mixture was stirred for 3 days. The reaction mixture was partitioned between water and ethyl acetate, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, and the combined organic layer was washed with saturated brine, followed by drying over sodium sulfate anhydrate. After a filtration step, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform – methanol), to thereby give the title compound (0.243 g, 74%) as an amorphous product. 1H-NMR(400MHz,CDCl3)delta:3.01(3H,s), 3.46(2H,br), 3.61(3H,s), 4.03(1H+1H×1/3,m), 4.42(1H+1H×2/3,m), 4.80(1H,br), 5.86(1H,br), 6.46-6.56(2H,m), 6.82(1H×2/3,br), 6.86(1H×1/3,br), 7.37-7.46(1H,m), 7.76-7.95(1H,m), 8.61-8.78(2H,m). ESI-MS m/z:365(M+H.)+., 109384-27-2

The synthetic route of 109384-27-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1762568; (2007); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

154590-34-8, tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3-fluoro-4-(N-t-butoxycarbonylpiperazin-1-yl) nitrobenzene (23 g, 72 mmol) (obtained according to the procedure described in preparation 2) in EtOAc (450 ml) 10% Pd/C (1.79 g) was added in portions while stirring. The reduction was carried out in the presence of H2 atmosphere maintained by inserting hydrogen balloon. After the reaction was(12-14 hrs. ), the contents were filtered through a celite bed. The solvent was removed from the filtrate under vacuum to provide the title compound (19.7 g, yield 93%), which was used for the next step without further purification.

154590-34-8, 154590-34-8 tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate 16203508, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; Orchid Chemicals &amp Pharmaceuticals Ltd; WO2004/18439; (2004); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

5308-25-8,5308-25-8, 1-Ethylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixed solution of a commercially available product of 1-(diphenylmethyl)azetidin-3-one (10.1 g, 42.6 mmol), TH-IF (100 mL) and acetic acid (5.00 mL) was added ethylpiperazine (6.48 mL, 51.1 mmol) at room temperature. The resultant mixture was stirred at room temperature for 45 minutes. Sodium triacetoxyborohydride (18.1 g, 85.1 mmol) was added to the reaction mixture at room temperature and then stirred at room temperature for 15 hours. Sodium hydrogen carbonate and water were added to the reaction mixture, and the resultant solution was then extracted with ethyl acetate. An organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by silica gel column chromatography (ethyl acetate-methanol) and was then further purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1 and the 1:1) to give the title compound (12.7 g, yield: 89%). 1H-NMR Spectrum (400 MHz, CDCl3) delta(ppm): 1.07 (3H, t, J=7.6 Hz), 2.20-2.65 (10H, m), 2.85-2.93 (2H, m), 2.95-3.05 (1H, m), 3.35-3.45 (2H, m), 4.41 (1H, s), 7.15-7.20 (2H, m), 7.23-7.29 (4H, m), 7.37-7.42 (4H, m).

The synthetic route of 5308-25-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Inoue, Satoshi; Yamamoto, Yuji; Iso, Kentaro; US2015/175615; (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.697305-48-9,1-(4-Fluorophenyl)piperazin-2-one hydrochloride,as a common compound, the synthetic route is as follows.

A mixture of 3-chloro-6-(1 H-pyrazol-4-yl)-8-(trifluoromethyl)imidazo[1 ,2- a]pyridine-2-carboxylic acid (0.097 g, 0.295 mmol), 1-(4-fluorophenyl)-2-piperazinone hydrochloride (0.068 g, 0.295 mmol), DIPEA (0.154 mL, 0.884 mmol) and HATU (0.135 g, 0.354 mmol) in DMF (2 mL) was stirred at room temperature for one hour. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by reverse phase HPLC (acetonitrile:water with 0.1 % formic acid) to give the title compound (0.045 g, 29%) as a white solid. 1H NMR (400 MHz, DMSO-c 6) delta ppm 13.19 (br. s., 1 H) 8.87 (s, 1 H) 8.59 (m, 1 H) 8.24 (m, 2 H) 7.33 – 7.61 (m, 2 H) 7.26 (t, 2 H) 4.69 (s, 1 H) 4.42 (m, 1 H) 4.13 – 4.29 (m, 1 H) 3.99 – 4.13 (m, 1 H) 3.81 (m, 2 H). ES-LCMS m/z: 507 (M+1 )., 697305-48-9

The synthetic route of 697305-48-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John, G.; CHONG, Pek, Yoke; FANG, Jing; GARRIDO, Dulce, Maria; PEAT, Andrew, James; PRICE, Daniel, J.; SHOTWELL, John, Brad; TAI, Vincent; ZHANG, Huichang; WO2011/41713; (2011); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics