Heterocyclic Building Blocks-piperazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.132710-90-8,1-Boc-4-(3-hydroxypropyl)piperazine,as a common compound, the synthetic route is as follows.

To 0.5 g (2.05 mmol) of tert-butyl 4-(3-hydroxypropyl)piperazine-1-carboxylate, 0.3 g (2.46 mmol) of 4-hydroxybenzaldehyde and 1 g (3.07 mmol) of resin-supported triphenyl-phosphine (3 mmol/g of resin) diluted in 14.5 ml of anhydrous tetrahydrofuran, is added dropwise at 0C under argon 0.614 ml (3.07 mmol) of diisopropyldiazene-1,2-dicarboxylate. The reaction mixture is stirred at room temperature for 20h. The solid is filtered then rinsed in dichloromethane. The filtrate is concentrated and diluted in a sodium hydroxide solution (1M) and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 4:6 to 100% ethyl acetate) to yield 0.58 g of tert-butyl 4-(3-(4-formylphenoxy)propyl)piperazine-l-carboxylate in the form of a colourless oil.LCMS (ESI, m/z): (M+l) 348.91H-NMR: deltaEta pm 400 MHz, DMSO: 9.87 (1H, s, CHO), 7.86 (2H, d, CH^), 7.12 (2H, d, CHaro , 4.13 (2H, t, CH2), 3.28-3.31 (4H, m, 2CH2), 2.44 (2H, t, CH2),2.31-2.34 (4H, m, 2CH2), 1.91 (2H, q, CH2), 1.40 (9H, s, 3CH3).

132710-90-8, As the paragraph descriping shows that 132710-90-8 is playing an increasingly important role.

Reference£º
Patent; PIERRE FABRE MEDICAMENT; BEDJEGUELAL, Karim; RABOT, Remi; KALOUN, El Bachir; MAYER, Patrice; MARCHAND, Arnaud; RAHIER, Nicolas; SCHAMBEL, Philippe; BIENAYME, Hugues; WO2011/45344; (2011); A1;,
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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

A mixture of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-ethoxy-7-fluoro-3- quinolinecarbonitrile (200 mg, 0.49 mmol), 3- (4-methyl-piperazin-1-yl) propanol (155 mg, 0.98 mmol) (WO 20047212) and sodium hydride (196 mg, 4.6 mmol) in 5 mL of N, N-dimethylformamide was heated at 125C for 3 hours. The reaction mixture was poured into saturated sodium bicarbonate and stirred for 1 hour. The aqueous solution was extracted with 10% methanol in dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin layer chromatography, eluting with 15% methanol in dichloromethane. Trituation with hexane provided 116 mg of 4-[(2, 4- dichloro-5-methoxyphenyl) amino]-6-ethoxy-7- [3- (4-methylpiperazin-1- yl) propoxy] quinoline-3-carbonitrile as a light brown solid, mp 137-138C. MS 542.0 (M-H) – Analysis for C27H31CI2N503-0. 6 H20 Calcd : C, 58.40 ; H, 5.84 ; N, 12. 61. Found: C, 58.31 ; H, 5.71 ; N, 12.43., 5317-33-9

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

Reference£º
Patent; WYETH; WO2005/47259; (2005); A1;,
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162046-66-4, 4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of carboxylic acid 17b (3.5 g, 11.4 mmol) in THF (15 mL)containing a drop of DMF was added 1?1?-carbonyldiimidazole (1.24 g, 13.7mmol) in a single portion. The mixture was left to stir at room temperature for 18hours. A stock solution of free-base guanidine was prepared as follows:Guanidine HCl (3.22 g, 34.2 mmol) was added to an aqueous NaOH solution (2M, 10 mL). The THF solution of the acyl imidazole was then added to the freebaseguanidine solution (10 mL) and stirred for 2 hours after which TLC indicatedcomplete consumption of the acyl imidazole and a more polar spot was observedon TLC. Spot stayed on the TLC baseline when using a solvent system of 10%MeOH in DCM but move to an RF ~of 0.4 when a few drop of 7 N NH3 in MeOHwas added to the TLC solvent. The mixture was concentrated in vacuo resulting in the formation of a pale yellowresidue which was dissolved in EtOAc (35 mL). The organic layer was washedwith water (3 x 25 mL), brine (1 x 30 mL), dried (Na2SO4), filtered, andconcentrated under vacuo to give a pale yellow syrup. The crude product wasfurther purified by flash column chromatography (silica gel, Silica Flash-Silicycle) using an eluent of dichloromethane, 5% MeOH in dichloromethane, and10% MeOH in dichloromethane to give an off-white syrup which was converted tothe hydrochloride salt using 1.25 M HCl in methanol. The methanolic solutionwas concentrated under vacuo to give 16 as a light yellow solid (540 mg, 11%)., 162046-66-4

As the paragraph descriping shows that 162046-66-4 is playing an increasingly important role.

Reference£º
Article; Jalily, Pouria H.; Eldstrom, Jodene; Miller, Scott C.; Kwan, Daniel C.; Tai, Sheldon S.-H.; Chou, Doug; Niikura, Masahiro; Tietjen, Ian; Fedida, David; Molecular Pharmacology; vol. 90; 2; (2016); p. 80 – 95;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1228780-72-0,1-((4′-Chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1′-biphenyl]-2-yl)methyl)piperazine,as a common compound, the synthetic route is as follows.

1228780-72-0, To a solution of 1 – ((4′-chloro-5,5-dimethyl-3,4,5,6-tetrahydro- [1,1′-biphenyl] -2-yl)Methyl) piperazine (1.62 g, 5.08 mmol, 1.12 eq)Compound 7 (1.30 g, 4.54 mmol, 1.0 eq)And dipotassium hydrogen phosphate(2.0 g, 13.0 mmol, 2.8 eq) and reacted at 140 C overnight under nitrogen. The reaction solution was poured into 100 mL of water and EA (40 mL x 3) was extracted. The organic phase was dried over anhydrous sodium sulfate, dried over the column, and the eluent was dried with PE / EA (v / v) = 3/1 The yellow oil was 1.4 g, yield 51.0%.

The synthetic route of 1228780-72-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sunshine Lake Pharma Co.,Ltd.; Kou, Yuhui; Hu, Bolin; Jiang, Haigang; Ye, Jiuyong; Liu, Zhiqiang; Xie, Hongming; Zhang, Yingjun; (42 pag.)CN106565706; (2017); A;,
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109-07-9, 2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,109-07-9

Reference Example 10 Benzyl 3-methylpiperazine-1-carboxylate A 4 g portion of 2-methylpiperazine was dissolved in 40 ml of dichloromethane, and 1.71 g of benzyl chloroformate was added dropwise thereto at -78C. After 1 hour of stirring, the mixture was washed by adding water and dried and then the solvent was evaporated to obtain 2.0 g of the title compound.

As the paragraph descriping shows that 109-07-9 is playing an increasingly important role.

Reference£º
Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1122242; (2001); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.438049-35-5,N-Boc-3-Ethylpiperazine,as a common compound, the synthetic route is as follows.

(RS) 1-Chlorocarbonyl-2-ethyl-4-tert-butoxycarbonylpiperazine a solution of (RS)4-tert-butoxycarbonyl-2-ethylpiperazine (3.95 g) and pyridine (1.64 ml) in DCM (35 ml) was added dropwise to a stirred solution of triphosgene (2.1 g) in DCM (100 ml) at 0 C. under Ar. The mixture was warmed to room temperature, stirred for 30 min then washed with water (100 ml) and brine (100 ml). The organic solution was dried (sodium sulfate) and concentrated in vacuo. The residue was dissolved in isohexane, filtered and concentrated in vacuo to give the product as a clear oil (3.73 g) which was used without further purification; deltaH (400 MHz, CDCl3) 4.39-3.80 (4H, m), 3.39-2.69 (3H, m), 1.66 (2H, m), 1.47 (9H, s), 0.96 (2.7H, d, J 7 Hz) and 0.89 (0.3H, d, J 7 Hz); GC (150 C. -10 min-320 C.) 83%, 8.72 min. (+/-)4-Difluoromethoxybenzyl-2-ethyl-4-tert-butoxycarbonylpiperazine-1-carboxylate:

438049-35-5, The synthetic route of 438049-35-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Adams, David Reginald; Bentley, Jonathan Mark; Davidson, James Edward Paul; Dawson, Claire Elizabeth; George, Ashley Roger; Mansell, Howard Langham; Mattei, Patrizio; Mizrahi, Jacques; Nettekoven, Matthias Heinrich; Pratt, Robert Mark; Roever, Stephan; Roffey, Jonathan Richard Anthony; Specklin, Jean-Luc; Stalder, Henri; Wilkinson, Kerry; US2002/143020; (2002); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.75336-86-6,(R)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Step 1 3-(R)-Methyl-piperazine-1-carboxylic acid tert-butyl ester Triethylamine (3 g, 4.2 mL, 30 mmol) was added to a solution of (R)-2-methyl piperazine (2 g, 20 mmol) in dichloromethane (40 mL) followed by di-tert-butyl-dicarbonate (4.8 g, 22 mmol). The reaction mixture was stirred at room temperature for 20 h. The mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate and brine and dried over sodium sulfate. The crude product was purified using a short plug of silica gel using hexane/ethyl acetate (1:1). 1H-NMR (CDCl3) delta: 1.05 (3H, d), 1.45 (9H, s), 2.11 (1H, s), 2.37-2.44 (1H, m), 2.66-2.79 (3H, m), 2.93-2.96 (1H, m), 3.93 (2H, br s). ESI-MS m/z: 201 (M+1)., 75336-86-6

As the paragraph descriping shows that 75336-86-6 is playing an increasingly important role.

Reference£º
Patent; Millennium Pharmaceuticals, Inc.; Kyowa Hakko Kirin Co., Ltd.; LULY, Jay R.; NAKASATO, Yoshisuke; OHSHIMA, Etsuo; HARRIMAN, Geraldine C.B.; CARSON, Kenneth G.; GHOSH, Shomir; ELDER, Amy M.; MATTIA, Karen M.; (190 pag.)US2016/31908; (2016); A1;,
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216144-45-5, 4-(4-Methylpiperazin-1-yl)benzylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The product (O from step 1 (190.00 mg, 369.21 muiotaetaomicronIota, 1.5 eq.) was taken in a flask along with DMF as a solvent. (4-(4-methylpiperazin-l-yl)phenyl)methanamine (50.53 mg, 246.14 muiotatauiotaomicronIota, 1 eq.), HOBT (66.52 mg, 492.28 muiotaetaomicronIota, 2 eq.), and DIC (66.70 muIota_, 430.75 muiotatauiotaomicronIota, 1.75 eq.) were added respectively at room temperature and stirred under N2. After 5 hours, the reaction was finished. The solution was quenched with water and then extracted with ethyl acetate. The organic layer was combined and dried with anhydrous MgS04 and concentrated in vacuo. The crude solid was purified through column chromatography using silica gel and dichloromethane: methanol (upto 3%) as an eluent. The product, 17, was a yellow solid with 80% yield. (0277) FT-IR (Neat) : v (cm”1) = 2930, 2849, 1736, 1698, 1693, 1655, 1650, 1632, 1603, 1561, 1537, 1503, 1440, 1380, 1349, 1327, 1239, 1177; 1H-NMR (400 MHz, CDCI3) : delta ppm 7.76 -7.83 (m, 2H), 7.58 – 7.61 (m, 1H), 7.21 – 7.31 (m, 4H), 6.95 – 7.01 (m, 2H), 6.91 (d, J = 8.56 Hz, 2H), 6.71 – 6.77 (m, 2H), 6.32 (br. s., NH), 4.50 (d, J = 5.54 Hz, 2H), 3.90 (s, 3H), 3.17 – 3.26 (m, 8H), 2.98 (s, 3H), 2.56 – 2.62 (m, 4H), 2.34 – 2.38 (m, 3H), 1.58 – 1.73 (m, 6H); 13C-NMR (100 MHz, CDCI3) : delta 166.25, 160.35, 153.25, 152.58 (2C), 150.88, 145.07, 136.15, 131.63, 131.11, 130.06 (2C), 129.31, 129.15, 128.26, 127.36, 125.91, 124.15, 119.52 (2C), 116.16 (2C), 114.38 (2C), 54.94 (2C), 52.12 (2C), 49.13, 48.86, 46.02, 43.67, 37.47, 31.72, 25.46 (2C), 24.25; HRMS-ESI (m/z) : calcd. for C37H43N505S2 = 701.2706, found = 701.2772., 216144-45-5

The synthetic route of 216144-45-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KING’S COLLEGE LONDON; THURSTON, David Edwin; KHONDAKER, Mirazur Rahman; JAMSHIDI, Shirin; NAHAR, Kazi Sharmin; (77 pag.)WO2019/30538; (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.21655-48-1,cis-2,6-Dimethylpiperazine,as a common compound, the synthetic route is as follows.

In a sealed tube, 2- (2, 8-dimethylimidazo [1 ,2-b]pyridazin-6-yl)-7-fluoro-pyrido [1,2- a]pyrimidin-4-one (Intermediate 2; 50 mg, 0.162 mmol), and cis-2,6-dimethylpiperazine (74 mg, 0.647 mmol, 4.0 eq.) were stirred in DMSO (1.5 mL) at 110C overnight. The solvent wasremoved under high vacuum. The residue was taken up in CH2C12 and washed with an aqueous saturated solution of NaHCO3. The organic layer was separated and dried over Na2504 and concentrated in vacuo. The crude was purified by column chromatography (5i02, CH2C12/MeOH=95/5 to 90/10) to afford the title product (32 mg, 49%) as a light yellow solid. MS m/z 404.4 [M+Hi.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ALSENZ, Jochem; GRASSMANN, Olaf; KUEHL, Peter; METZGER, Friedrich; MCCARTHY, Kathleen Dorothy; MORAWSKI VIANNA, Eduardo Paulo; WOODHOUSE, Marvin Lloyd; (130 pag.)WO2017/80967; (2017); A1;,
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373608-48-1, tert-Butyl 4-(3-aminopropyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 1662-[5-Methyl-2-(3-piperazin-1-ylpropylamino)-pyrimidin-4-yl]-benzo[b]thiophene-6-carboxylic acid methylamide tri-hydrochloride; A mixture of 2-(2-chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-6-carboxylic acid methylamide (263 mg, 0.830 mmol), 4-(3-aminopropyl)-piperazine-1-carboxylic acid tert-butyl ester (358 mg, 1.47 mmol) and diisopropylethylamine (0.44 mL) in 1,4-dioxane (10 mL) is heated at 95 C. for 20 hours. The solvent is removed after cooling and the residue is subjected to chromatography on silica gel, eluting with 2.0 M NH3/MeOH in dichloromethane 0-10%, to give 4-{3-[5-methyl-4-(6-methylcarbamoyl-benzo[b]thiophen-2-yl)-pyrimidin-2-ylamino]-propyl}-piperazine-1-carboxylic acid tert-butyl ester (191 mg, 44% yield). The intermediate is dissolved in THF (8 mL) and 5 N hydrochloric acid (5 mL) is added. The solution is heated at 70 C. for 4.5 hours and then cooled before evaporating the solvent. Methanol is added to the residue and the mixture is sonicated for 30 minutes. The solid is filtered and washed with diethyl ether, then dried in a vacuum oven at 50 C. for 18 hours to give the title compound (129 mg, 66% yield). ES+(m/z) 425 [M(free base)+H].

373608-48-1, As the paragraph descriping shows that 373608-48-1 is playing an increasingly important role.

Reference£º
Patent; Dahnke, Karl Robert; Lin, Ho-Shen; Richett, Michael Enrico; Shih, Chuan; Wang, Q May; Zhang, Bo; US2008/306082; (2008); A1;,
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