Heterocyclic Building Blocks-piperazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13484-40-7,1-(2-Methoxyethyl)piperazine,as a common compound, the synthetic route is as follows.

Example 121-(2-(2-(4-(2-methoxyethyl)piperazin-1-yl)pyrimidin-4-yloxy)benzyl)-3-(3-t-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea [Show Image] To a solution of 1-(2-(2-chloropyrimidin-4-yloxy)benzyl)-3-(3-t-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea (227 mg) in ethanol (1.0 mL), 1-(2-methoxyethyl)piperazine (80 mg) and N,N-diisopropylethylamine (0.5 mL) were added, and the resulting mixture was stirred at room temperature for 4 days. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The obtained residue was purified by amine-silica gel column chromatography (ethyl acetate/n-hexane = 1/1 – 2/1) to obtain the desired product (212 mg, yield: 76.5%). 1H-NMR (CDCl3):delta 8.13 (d 1H J = 5.6 Hz) 7.34-7.06 (m 8H) 6.20 (s 1H) 5.99 (s 1H) 5.90 (d 1H J = 5.6 Hz) 5.28 (t 1 H J = 5.9 Hz) 4.34 (d 2H J = 5.9 Hz) 3.68 (br 4H) 3.51 (t 2H J = 5.6 Hz) 3.35 (s 3H) 2.57 (t 2H J = 5.6 Hz) 2.46-2.44 (m 4H) 2.37 (s 3H) 1.32 (s 9H) MS (ESI):599 (M+H+)

13484-40-7, The synthetic route of 13484-40-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; TORAY INDUSTRIES, INC.; EP1970375; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

1228780-72-0, 1-((4′-Chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1′-biphenyl]-2-yl)methyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound J, methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)- 4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoate, may be prepared as follows. A mixture of Compound I (1.55 g), Compound F (2.42 g), and HK2PO4 (1.42 g) in dimethylsulfoxide (20 mL) at 135 C. was stirred for 24 hours. The reaction was cooled, diluted with ether (400 mL), and washed with 3×1M NaOH, and brine, and concentrated. The crude product was chromatographed on silica gel with 10-50% ethyl acetate/hexanes to provide the product (Compound J).

1228780-72-0, As the paragraph descriping shows that 1228780-72-0 is playing an increasingly important role.

Reference：
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (732 pag.)WO2016/24230; (2016); A1;,
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Piperazines – an overview | ScienceDirect Topics

103-76-4, N-(2-Hydroxyethyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 1-(2-hydroxyethyl)piperazine (26 g, 0.2 mol) in DMF (200 mL) was added formic acid (752 mL, 0.2 mol) and formaldehyde (16.2 g, 0.2 mol, 37% solution in water). The reaction mixture was cautiously heated at 100 C. for 2 hours then stirred overnight at room temperature. The solvent was removed in vacuo. This procedure was repeated 3 further times to give 100 g of product. The crude products were combined and distilled under vacuum to give, at 74 C., 2-(4-methylpiperazin-1-yl)ethanol (51 g, 44%) as a colourless liquid.Analytical LCMS: (System B, RT=0.70 min), ES+: 145.1 [MH]+., 103-76-4

103-76-4 N-(2-Hydroxyethyl)piperazine 7677, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; Biovitrum AB; US2009/203695; (2009); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

5625-67-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5625-67-2,Piperazin-2-one,as a common compound, the synthetic route is as follows.

1 Syntheis of 4-tert-Butoxycarbonyl-2-oxopiperazine Di-tert-butyl dicarbonate (10.4 g, 47.6 mmol) was added to a stirred solution of 2-oxopiperazine (4.77 g, 47.6 mmol) in ethanol (100 ml) at room temperature. After stirring at room temperature for 1 hour, the reaction mixture was concentrated in vacuo to give 4-tert-butoxycarbonyl-2-oxopiperazine as colorless crystals (8.00 g, 84%), which were collected by filtration and washed with hexane. 1H-NMR (200 MHz, CDCl3) delta: 6.90-6.56 (1H, m), 4.09 (2H, s), 3.64 (2H, t, J=5.2 Hz), 3.44-3.34 (2H, m), 1.48 (9H, s). IR (KBr): 3265, 3195, 2981, 1691, 1666, 1635, 1419, 1398, 1365, 1338, 1243, 1176, 1131, 1002 cm-1.

The synthetic route of 5625-67-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Takeda Chemical Industries, Ltd.; US6235731; (2001); B1;,
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.21655-48-1,cis-2,6-Dimethylpiperazine,as a common compound, the synthetic route is as follows.

Example 14 7-[(3R,5S)-3,5-dimethylpiperazin-l-yl]-2-(2-methylimidazo[l,2-b]pyridazin-6- yl)pyrido[l,2-a]pyrimidin-4-one In a sealed tube, 7-fluoro-2-(2-methylimidazo[l,2-b]pyridazin-6-yl)-4H-pyrido[l,2- a]pyrimidin-4-one (Intermediate 1; 50 mg, 0.169 mmol), and cis-2,6-dimethylpiperazine (77 mg, 0.677 mmol, 4.0 eq.) were stirred in DMSO (2 mL) at 110C overnight. The solvent was removed under high vacuum. The residue was taken up in CH2C12 and washed with an aqueous saturated solution of NaHC03. The organic layer was separated and dried over Na2S04 and concentrated in vacuo. The crude was purified by column chromatography (Si02, CH2Cl2/MeOH=95/5 to 90/10) to afford the title product (41 mg, 62%) as a light yellow solid. MS m/z 390.3 [M+H+]., 21655-48-1

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

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PTC THERAPEUTICS INC.; RATNI, Hasane; GREEN, Luke; NARYSHKIN, Nikolai A.; WEETALL, Marla L.; (80 pag.)WO2015/173181; (2015); A1;,
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Piperazines – an overview | ScienceDirect Topics

196811-66-2, tert-Butyl 4-carbamothioylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of tert-butyl 4-carbamothioylpiperazine-1-carboxylate (synthesized according to Example 5, Step 1, 2 g, 13.75 mmol) in dioxane (20 mL), triethyl amine (1.7 mL, 12.24 mmol) and 1-bromo-3,3,3-trifluoro acetone (3.2 g, 16.5 mmol) were added and stirred at 90 C for 3 h. The completion of the reaction was monitored by TLC. The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (2 x 25 mL). The organic layer was separated, dried over anhydrous Na2SO4, concentrated under vacuum and was used as such for next step. Yield: 75% (1 .0 g, white solid). 1 H NMR (300 MHz, DMSO-d6): delta 7.57 (s, 1H), 3.42 (m, 8H), 1.40 (s, 9H). LCMS: (Method A) 338.0 (M+H), Rt. 5.37 min, 99.0% (Max)., 196811-66-2

The synthetic route of 196811-66-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); 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.414910-15-9,tert-Butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.,414910-15-9

Preparation of N-cyclopropanoyl piperazinium p-toluenesulfonate (compound A) N-Boc-4-cyclopropanoyl piperazine (20.00 g, 78.64 mmol, 1.0 equiv.) and p-toluenesulfonic acid (p-TSA) monohydrate (15.71 g, 82.60 mmol, 1.05 equiv.) and ethyl acetate (EtOAc) (160 mL, 8 vol.) were added to a 3-necked 250 mL flask equipped with 5 cm stir bar, condenser, thermal couple and N2 inlet. The resulting mixture was heated to 50 C. overnight. The reaction was monitored by TLC. Upon completion, the suspension was cooled to 0 C. in ice bath and stirred for 1 hour. After stirring, the resulting slurry was filtered through Buchner funnel. The obtained wet cake was washed with EtOAc (20.0 mL, 1 vol.) twice (and dried at not more than 60 C. under vacuum overnight to afford compound A as white solid (23.12 g, 70.83 mmol, 90.08% Yield). 1H NMR (400 MHz, CDCl3) ?: 0.75 (m, 2H), 0.94 (m, 2H), 1.61 (m, 1H), 2.35 (s, 3H), 3.23 (br, 4H), 3.86 (br, 4H), 7.19 (d, J=8.2 Hz, 2H), 7.69 (d, J=8.2 Hz, 2H), 9.20 (br, 1H).

The synthetic route of 414910-15-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SCINOPHARM TAIWAN, LTD.; HSIAO, Tsung-Yu; CHANG, Yung-Hung; (16 pag.)US2018/57464; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129799-15-1, Methyl 1-Boc-piperazine-2-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of methyl 1-Boc-piperazine-2-carboxylate (0.5 g, 2 mmol) in CH2Cl2 (10 ml) was added PhSO2Cl (0.53 ml,4.1 mmol) and Et3N (0.57 ml, 4.1 mmol) at room temperature. The resulting solution was stirred overnight. The reaction was washed with 1 N NaHCO3 (40mL x 3), brine and dried over Na2SO4. The product was purified via flash chromatography (10% EtOAc/Hexanes; 20% EtOAc/Hexanes; 50% EtOAc/Hexanes) to give an off-white solid Methyl 1-Boc-4-benzenesulfonyl-piperazine-2-carboxylate in 91% yield., 129799-15-1

The synthetic route of 129799-15-1 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Zhao, Huanyu; Prosser, Anthony R.; Liotta, Dennis C.; Wilson, Lawrence J.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 21; (2015); p. 4950 – 4955;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

52385-79-2, 2-(3-Chlorophenyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 300 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[3-(2-piperazinyl)phenyl]-1H-indole-7-carboxamide trifluoroacetate To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (60 mg, 0.13 mmol) in dioxane (1.5 mL) and water (0.5 mL) was added 2-(3-chlorophenyl)piperazine (63.7 mg, 0.325 mmol) and potassium carbonate (90 mg, 0.650 mmol). This mixture was degassed for 5 min then tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.011 mmol) was added. The resulting mixture was reacted in a microwave for 30 min at 160 C. The solid was filtered off and all solvents were evaporated. The resulting solution was re-dissolved in dichloromethane and separator was used to remove water. The mixture was concentrated to give organic solvent and then purified by Gilson Preparatory HPLC to give 21.7 mg of the title compound (27.4%). LC/MS=m/z 496.4 [M+H] Ret. Time: 1.28 min., 52385-79-2

As the paragraph descriping shows that 52385-79-2 is playing an increasingly important role.

Reference：
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

13889-98-0, 1-Acetylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-{4-[3-(6-Bromo-quinazolin-4-yl)-5-fluoro-benzoyl]-piperazin-1-yl}-ethanone To a mixture of 3-(6-bromo-quinazolin-4-yl)-5-fluoro-benzoic acid (1.36 g, 3.72 mmol) in CH2Cl2 (15 mL) was added DIPEA (1.30 mL, 7.44 mmol) and HBTU (1.694 g, 4.47 mmol) at rt. The reaction mixture was stirred at rt for 20 min. To the mixture was then added 1-(piperazin-1-yl)ethanone (0.572 g, 4.47 mmol) and the reaction mixture was stirred at rt for 1 h. The reaction was quenched with a saturated aqueous solution of NaHCO3 and extracted with CH2Cl2. The organic layer was washed twice with brine, dried by passing through a phase separating cartridge and evaporated. Purification by Flash chromatography using Biotage Isolera system (amine functionalized silica KP-NH, eluting with Cyclohexane/EtOAc 0 to 100%) gave the title compound (1.20 g, 68% yield) as a beige foam. MS: 457.4-459.3 [M+1]+, Rt(2′)=1.03 min., 13889-98-0

The synthetic route of 13889-98-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics