Heterocyclic Building Blocks-piperazine

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.

Step 1: (S)-tert-butyl-2-methyl-4-phenylpiperazine-1-carboxylate To a solution of iodobenzene (2.08 g, 10.19 mmol) in toluene (60 mL) at rt was added (S)-tert-butyl-2-methylpiperazine-1-carboxylate (1.7 g, 8.49 mmol), Pd2(dba)3 (778 mg, 0.85 mmol), t-BuONa (2.44 g, 25.46 mmol), XantPhos (982 mg, 1.70 mmol) under nitrogen. The reaction mixture was stirred at 100 C. for 16 h, then cooled to rt and diluted with EtOAc (60 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and purified by chromatography (silica, EtOAc/PE=1/10) to afford (S)-tert-butyl-2-methyl-4-phenylpiperazine-1-carboxylate (1.8 g, 6.5 mmol, 64%) as an oil. ESI-MS (EI+, m/z): 277.2 [M+H]+., 169447-70-5

The synthetic route of 169447-70-5 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; (136 pag.)US2019/389843; (2019); 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.74879-18-8,(S)-(+)-2-Methylpiperazine,as a common compound, the synthetic route is as follows.

A mixture of Intermediate 41 (0.3g), (2S)-2-methylpiperazine (CAS No 74879-18-8) (0.1g) and TEA (0.12g) in methanol (20.OmL) is heated at 650C for 4 hours. The solvent is evaporated in vacuo. Purification of the residue by column chromatography on silica, eluting with DCM / methanol (95:5), affords the title compound as a white solid (0.26g, 73%). LCMS 362/364 [M+H]+, RT 2.24 mins (pH 5.8). 1H NMR 300 MHz (CDCI3) (delta ppm):8.15 (1 H, d), 7.60 (1 H, dd), 7.40 (1H, d), 4.85 (4H, m) 3.15 (2H, m), 2.95 (2H, m), 2.75(1 H, t), 1.95 (3H, d)., 74879-18-8

As the paragraph descriping shows that 74879-18-8 is playing an increasingly important role.

Reference£º
Patent; UCB PHARMA, S.A.; WO2008/74445; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

4318-42-7, 1-Isopropylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 4-bromobenzoic acid 1-12 at 0¡ãC (2 g, 9.94 mmol) in a mixture of MeC : DMF (4:1, 20 mL) were added HATU (4.53 g, 11.93 mmol) and 1-isopropylpiperazine (1.91 g, 14.92 mmol). The reaction mixture was allowed to stir for 30 minutes, and then diisopropylethylamine (3.85 g, 5.2 mL, 29.84 mmol) was added thereto. The resulting reaction mixture was stirred for 16 hours at room temperature. After completion of reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (25 mL x 3) . The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel ‘(60-120 mesh size) column chromatography using 0-5 percent methanol in dichloromethane as eluent to give the desired product 1-13 (3.0 g, 97percent) as brown solid; LCMS: m/z 312.00 (M+l) .

4318-42-7, As the paragraph descriping shows that 4318-42-7 is playing an increasingly important role.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (284 pag.)WO2015/88045; (2015); A1;,
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3022-15-9, Piperazine-2-carboxylic acid dihydrochloride is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,3022-15-9

EXAMPLE IX; Synthesis of Piperazine derivatives; Chemical Formula: C16H2iN3Oe Chemical Formula: C12H15N304 Molecular Weight: 130.15 Molecular Weight: 351.35 Molecular Weight: 265.27a: Boc-ON, NaOH, Dioxaneb: 2-flouronitrobenzene, K2C03, DMSOc: SOCI2, methanol, reflux, 2hrsd: Fmoc-NCS, CH2CI2/DMF; 20% piperidine in methanole: appropriate bromoacetophenonef: 1 N NaOH, Dioxane, reflux, 0.5hrs4-(feri-butoxycarbonyl)piperazine-2-carboxylic acid; [191] 4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid : To a solution of 2-piperazine- carboxylic acid dihydrochloride (1.0 g, 4.92 mmol) in 20 mL of water/dioxane 1 : 1, NaOH 6N was added to adjust the pH to 11. A solution of BOC-ON (1.34 g, 5.41 mmol) in dioxane (5 mL) was then added dropwise, while maintaining the pH=l 1 during the addition and the resulting solution was stirred overnight at room temperature. Another 0.134 g of BOC-ON were added and the reaction mixture was stirred for 2h. The solvent was evaporated under reduced pressure and the residue was diluted with diethyl ether/water (60 mL). The phases were separated and the pH of the aqueous layer was adjusted to 7 by slow addition of HC1 IN. Evaporation of water under reduced pressure afforded the title compound as a white solid which was dried in a vacuum oven at 50 C and used without further purification for the next step.

3022-15-9 Piperazine-2-carboxylic acid dihydrochloride 2723757, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; CHOREV, Michael; AKTAS, Bertal Huseyin; HALPERIN, Jose A.; WAGNER, Gerhard; WO2012/6068; (2012); A2;,
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Piperazines – an overview | ScienceDirect Topics

75336-86-6,75336-86-6, (R)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred mixture of 4-fluoronitrobenzene (2.0 g, 0.014 mol, 1.0 eq) in DMF (50 mL) at rt, (R)-2-methylpiperazine (1.1 eq) and K2CO3 (3.0 eq) were added and stirred at rt for 16 h. After TLC showed completion of starting material, the mixture was diluted with water (100 mL) and extracted with EtOAc (3 x 150 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous sodium sulphate, and concentrated to provide crude residue. The crude was triturated with n-hexane and filtered to obtain (R)-3-methyl-l-(4-nitrophenyl)piperazine (2.6 g, 84percent) as yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 8.028 (d, 2H), 7.002 (d, 2H), 3.860 (m, 2 H), 2.952 (d, 1H), 2.887 (t, 1H), 2.790 (m, 2H), 2.450 (m, 1H), 2.331 (s, 1H), 1.023 (d, 3H).

The synthetic route of 75336-86-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASANA BIOSCIENCES, LLC; VENKATESAN, Aranapakam M.; SMITH, Roger A.; THOMPSON, Scott K.; LAPING, Nicholas; KULKARNI, Bheemashankar; HALLUR, Gurulingappa; VISWANADHAN, Vellarkad N.; PENDYALA, Muralidhar; KETHIRI, Raghava Reddy; TYAGI, Rajiv; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; WO2015/38417; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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

(a) (2S,5R)-2,5-Dimethyl-4-(5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester A mixture of 2-chloro-5-nitropyridine (1.0 g, 6.3 mmol), (2S,5R)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 6.3 mmol), and potassium carbonate (1.7 g, 13 mmol) was stirred in DMSO (5.0 mL, 70 mmol) at 100 C. overnight. The reaction mixture was filtered thru a silica gel pad, which was washed with EtOAc (200 mL). The filtrate was washed with water (2*10 mL), concentrated, and purified by silica gel chromatography (eluted with ethyl acetate/hexane=0 to 80%) to give the title intermediate (1.724 g, 81% yield) as a yellow solid.

548762-66-9 (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate 11745988, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

252990-05-9, Methyl (R)-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 Compound 13A (605 mg, 2.46 mmol), l-(/er/-butyl) 2-methyl (f?)-piperazine-l,2-dicarboxylate (500 mg, 2.05 mmol), and K2CO3 (424 mg, 3.07 mmol) in DMF (10 mL) was stirred at 60 C for 4 hours. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 2). The combined organic extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to yield Compound 13B-1: LC-MS (ESI) m/z: 411 [M+H]+.

252990-05-9, The synthetic route of 252990-05-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; (270 pag.)WO2019/104011; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

1001180-21-7, (R)-tert-Butyl 4-(5-methyl-7-oxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 40; 2-(4-chlorophenyl)-l-(‘4-((5R)-7-hydroxy-5,7-diniethyl-6,7-dihvdro-5H-cvclopenta[dlpyrimidin-4- vDpiperazin- 1 -ylV S-fisopropylamino’propan- 1 -one; Step 1 :; A solution of (R)-tert-butyl 4-(5-methyl-7-oxo-6,7-dihydro-5H- cyclopenta[d]pyrimidin-4-yl)piperazine-l-carboxylate (40 nig, 0.120 mmol) in THF (4 niL) was added to a 1.5M solution of methyllithium in diethyl ether (0.088 mL, 0.132 mmol) at -780C. The resulting mixture was stirred at -78C for 1 hour and quenched by saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (2 X). The organic layer was dried (MgSO^ and concentrated. The residue was purified by a silica catridge (5.0 g) eluted by EtOAc to give tert-butyl 4-((5R)-7-hydroxy-5,7-dimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine- 1-carboxylate as an off-white solid (29 mg, 69%). LCMS (APCI+) [M-Boc+H]+ 349.1; Rt: 2.49 min.

1001180-21-7, The synthetic route of 1001180-21-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; MITCHELL, Ian, S.; BLAKE, James, F.; XU, Rui; KALLAN, Nicholas, C.; XIAO, Dengming; SPENCER, Keith, Lee; BENCSIK, Josef, R.; LIANG, Jun; SAFINA, Brian; ZHANG, Birong; CHABOT, Christine; DO, Steven; WO2008/6040; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

278788-66-2, (R)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: tert-Butyl (3R)-4- [2-(4-cyano-3-methoxyphenyl)-2-hydroxyethyli -3 (hydroxymethyl)piperazinel-carboxylate: A Pyrex vessel was charged with magnetic stirring bar, (2.0 g, 11.42 mmol) of 2-methoxy-4-(oxiran-2-yl) benzonitrile, (3.70 g, 17.12 mmol) of tert-butyl (3R)-3- (hydroxymethyl)piperazine-1-carboxylate, and 6 mL of EtOH. Then it was introduced in themicrowave reactor and irradiated at 150 C for 3 h. The mixture was cooled to room temperature and the solvent was evaporated and the resulting residue was purified by column chromatography (silica gel, 1- 20% dichloromethane/MeOH) which afforded the product as a mixture of two diastereomers (1:1) LC/MS: (IE, m/z) [(M + 1)- t-Bu] = 336.41, 278788-66-2

278788-66-2 (R)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate 24820286, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DEJESUS, Reynalda, Keh; FRIE, Jessica, L.; PIO, Barbara; TANG, Haifeng; WALSH, Shawn, P.; WO2014/99633; (2014); A2;,
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

N-(2-((2-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methylphenyl)-N- methylmethanesulfonamide (250 mg, 0.686 mmol), tert-butyl 4- (4- aminophenyl)piperazine- l-carboxylate (133 mg, 0.480 mmol), potassium carbonate (284 mg, 2.058 mmol) and X-Phos (33 mg, 0.0686 mmol) in iert-butanol (10 mL) were combined under argon atmosphere. The mixture was purged with argon for 30 min and then tris(dibenzylideneacetone)dipalladium (31 mg, 0.0343 mmol) was then added to the mixture. The mixture was stirred for 3 h at 100C. Progress of the reaction was followed by TLC (5% MeOH/DCM). After completion of the reaction, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (75 mL x 2). The combined organic slayer were washed with brine solution (50 mL), dried over Na2S04, filtered and evaporated to provide crude product. The resulting residue was purified by Biotage Isolera system by using 2% MeOH/DCM to give tert-butyl 4-(4-((7-(5-methyl-2-(N- methylmethylsulfonamido)benzyl)-7H-pyrrolo[2,3-d]pyrimidin-2- yl)amino)phenyl)piperazine-l-carboxylate (Yield: 230 mg, 55.4 %). 1H NMR (400 MHz, DMSO-d6): delta 9.09 (s, 1H), 8.64 (s, 1H), 7.63-7.61 (d, 2H, J=8 Hz), 7.46-7.43 (d, 1H, J=12 Hz), 7.16-7.15 (d, 2H, J=4 Hz), 6.84-6.82 (d, 2H, J=8 Hz), 6.73 (s, 1H), 6.45-6.44 (d, 1H, J=4 Hz), 5.3 (brs, 1H), 5.5 (brs, 1H), 3.45-3.42 (t, 4H, J=8 Hz), 3.11 (s, 3H), 3.08 (s, 3H), 2.97-2.94 (t, 4H, J=8 Hz), 2.14 (s, 3H), 1.40 (s, 9H).

170911-92-9, The synthetic route of 170911-92-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASANA BIOSCIENCES, LLC; VENKATESAN, Aranapakam M.; SMITH, Roger A.; THOMPSON, Scott K.; LAPING, Nicholas; KULKARNI, Bheemashankar; HALLUR, Gurulingappa; VISWANADHAN, Vellarkad N.; PENDYALA, Muralidhar; KETHIRI, Raghava Reddy; TYAGI, Rajiv; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; WO2015/38417; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics