Category: 171504-98-6

171504-98-6, Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 1,4-di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (5.09 g, 14.7 mmol) in dry THF (49 mL) was added methylmagnesium bromide (3.0 M in THF and tol, 31.7 mL, 44.3 mmol) at 0 C. The reaction mixture was stirred at room temperature for 18 hours. After quenched with saturated aq. NH4Cl, the mixture was diluted with water and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=5:1 to 3:1 to 2:1) to afford di-tert-butyl 2-(2-hydroxypropan-2-yl)piperazine-1,4-dicarboxylate (2.47 g, 48%) as a colorless viscous oil. 1H-NMR (CDCl3, Varian, 400 MHz): delta 1.21 (3H, s), 1.31 (3H, s), 1.46 (18H, s), 3.01-3.38 (4H, m), 3.79-4.21 (4H, m)., 171504-98-6

As the paragraph descriping shows that 171504-98-6 is playing an increasingly important role.

Reference：
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (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.171504-98-6,Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate,as a common compound, the synthetic route is as follows.

To a stirring solution of compound 2 (1 g, 2.91 mmol) in dry THF (20 mL) were added LiHMDS (1.0 M in THF) (10.2 mL, 10.2 mmol), paraformaldehyde (69 mg, 2.32 mmol) at -78 C under nitrogen atmosphere. The reaction mixture was brought to RT and stirred for 16 h. After consumption of the starting material (by TLC), the reaction was quenched with ice water (20 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layer was washed with brine solution (2 x 10 mL), dried over Na2S04 and concentrated to obtain crude compound which was purified by column chromatography by eluting 30% EtOAc/ hexanes to afford racemic EE (320 mg, 32%) as white solid. The racemic was separated by chiral HPLC purification to give 75mg each of EE-1 and EE-2. EE-1: 1H-NMR: (400 MHz, DMSO-d6): delta 7.98 (s, 1H), 3.78 (d, / = 12.8 Hz, 1H), 3.67-3.60 (m, 1H), 3.51 (d, / = 13.6 Hz, 1H), 3.41-3.30 (m, 4H), 3.07 (br s, 1H), 1.39 (s, 18H). LCMS (ESI): m/z 340.1 [M+-l]; UPLC: 99.74% EE-2: 1H-NMR: (400 MHz, DMSO-ifc): delta 7.99 (s, 1H), 3.78 (d, / = 12.8 Hz, 1H), 3.65-3.61 (m, 1H), 3.51 (d, / = 13.6 Hz, 1H), 3.40-3.30 (m, 4H), 3.07 (br s, 1H), 1.39 (s, 18H). LCMS (ESI): m/z 340.1 [M+-l]; UPLC: 99.04%, 171504-98-6

The synthetic route of 171504-98-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; APTINYX INC.; KHAN, M., Amin; (75 pag.)WO2018/26782; (2018); 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.171504-98-6,Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate,as a common compound, the synthetic route is as follows.

General procedure: To a solution of 1 ,4-di-tert-butyl 2-methyl piperazine-l,2,4-tricarboxylate 29 (l.Og, 2.9 mmol) in DCM (20mL) was added TFA (2.3 lg, 20.3 mmol) at 0C. The reaction mixture was stirred at RT for 4h. TLC analysis indicated complete conversion of SM. Reaction was concentrated to remove excess of TFA and sticky solid so obtained was taken in DCM (20 mL). To this suspension, HATU (1.65g, 4.34 mmol), NMM (293 mg, 2.9 mmol), 3- formylbenzoic acid (435 mg, 2.9 mmol), and DMAP (lOmg) were added. Reaction mixture was stirred at RT for 16 h. The reaction was monitored by LCMS. The reaction mixture was diluted with DCM and washed with water; organic layer was separated, dried over Na2SC>4 and concentrated under reduced pressure. The sticky solid so obtained was added to a solution of NaOH (65mg, 1.6 mmol) in MeOH (5mL). Reaction mixture was stirred at rt for 7h. The reaction was monitored by TLC. When SM was completely consumed, reaction mixture was concentrated under vacuum. The solid was suspended in water and acidified to pH 6 using 1 N HC1. The suspension was filtered and the precipitate was triturated with ethanol to give 766 mg (20%) of 4-(3-formylbenzoyl)piperazine-2- carboxylic acid 32 as sticky solid. LCMS (254nm): [M+H]+ 276.95 (100%).

171504-98-6, The synthetic route of 171504-98-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; CEPHALON, INC.; BRESLIN, Henry J.; CURRY, Matthew A.; GINGRICH, Diane E.; LEARN, Keith S.; OTT, Gregory R.; WAGNER, Jason C.; WO2013/116291; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

171504-98-6, Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 142: (+/-)-1 ,4-bis(1 ,1-dimethylethyl) 2-methyl 2-methyl-1 ,2,4- piperazinetricarboxylate; In a 500ml round-bottomed flask, 12 g of intermediate 141 (34.8 mmole) were dissolved in 240 ml. of THF to give a colourless solution. 38.3 ml. of LiHMDS 1 M in THF (38.3 mmole) were added dropwise to the solution keeping the mixture to -78C. The reaction was allowed to stir at this temperature for 1 h. 2.40 ml. of iodomethane (38.3 mmole) were added dropwise at -78C and the reaction was allowed to stir at this temperature for 1 h. The mixture was warmed to -200C and it was allowed to react at this temperature for 2 h. The reaction was almost complete and was cooled to -78C and 12 ml. of LiHMDS 1 M in THF (12 mmole, 1 M sol. In THF) and 1.2 mL of iodomethane (19 mmole) were added successively at this temperature. Then the mixture was warmed to -200C and after 1.5 h a TLC control showed then the reaction was finished. The mixture was quenched at 00C with 150 mL of a saturated solution of ammonium chloride. Then the mixture was allowed to reach RT. The two phases were separated and the aqueous was extracted with 2×200 mL of AcOEt. The resulting organic layer was dried over Na2SC>4, filtered and evaporated under reduced pressure to obtain 12.2 g of desired product as a crude oil. UPLC-MS [Acquity UPLC BEH C18, 50×21 mm, 1.7 mum, Mobile phases: A: H2O +0.1% HCOOH/B: MeCN+0.06% HCOOH; Gradient: t=0 min: 97%A, 3% B t= 0.1 min 94%A, 6%B t=0.6min 30%A, 70%B t=1.10min 1%A, 99%B t=1.45 min 97%A, 3%B t=1.50min 97%A ,3%B flow rate: 1 mL/min, UV range wavelength 210-350nm] R1 = 0.80 min , m/z (ES): 359 [M+H]+., 171504-98-6

Big data shows that 171504-98-6 is playing an increasingly important role.

Reference：
Patent; GLAXO GROUP LIMITED; WO2008/148853; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

171504-98-6, Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: (0892) To a solution of DIPA (3.67 g, 36 mmol, 1.2 eq) in THF (18 mL) was added n-BuLi (2M, 18 mL, 1.2 eq) dropwise at -78 C. over 15 min and the mixture was stirred for another 15 min at -78 C. Then compound AH (10.3 g, 30 mmol, 1.0 eq) in THF (30 mL) was added dropwise to the reaction at -78 C., after the addition was completed, the mixture was stirred for another 30 min at -78 C. BOMC1 (7 g, 45 mmol) in THF (20 mL) was added dropwise over 20 min at -78 C., the reaction mixture was stirred for 16 h and the temperature was warmed to rt during this period. The reaction was quenched with 1M HCl (50 mL), extracted with EA (100 mL) two times, the organic layer was dried and concentrated, the residue was purified on silica gel (EA/PE: 0%-20%) to give compound 90-C-1 as colorless oil (8.2 g)., 171504-98-6

The synthetic route of 171504-98-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HOFFMANN-LA ROCHE INC.; Guo, Lei; Hu, Taishan; Kou, Buyu; Lin, Xianfeng; Shen, Hong; Shi, Houguang; Yan, Shixiang; Zhang, Weixing; Zhang, Zhisen; Zhou, Mingwei; Zhu, Wei; US2015/252057; (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.171504-98-6,Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate,as a common compound, the synthetic route is as follows.

(B) 1,4-Di-(N-tert-Butoxycarbonyl)-2-Piperazinecarboxylic Acid A solution of 1 N sodium hydroxide (1.2 mL) was added to a solution methyl 1,4-di-(N-tert-butoxycarbonyl)-2-piperazinecarboxylate (A, 290 mg) in methanol (10 mL). The mixture was stirred at room temperature for 12 hr and evaporated in vacuo. The residue was diluted with water and washed with ether. The aqueous layer was acidified with 10% citric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give the title compound (230 mg) as a colorless foam: 1H NMR (400 MHz, CDCl3) delta 1.44 (s,18H) and 4.56-4.75 (m, 1H)., 171504-98-6

The synthetic route of 171504-98-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Microcide Pharmaceuticals, Inc.; US6399629; (2002); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

171504-98-6, Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add 1,4-di-tert-butyl 2-methylpiperazine-1,2,4-tricarboxylate (10 g) to the dry reaction flask.29.04mmol),Anhydrous tetrahydrofuran (100 mL),Under nitrogen protection, cool down to -78 C,Slowly add LiHDMS (35 mL, 35 mmol, 1 mol/L).After stirring for 2 h, iodomethane (3.7 mL, 59 mmol) was added.Stirring was continued for 1 h, slowly warmed to room temperature, and stirring was continued for 12 h.The reaction was quenched by adding a saturated aqueous solution of ammonium chloride (50 mL), and then ethyl acetate(100 mL ¡Á 2), the organic layer was combined, and the organic layer was evaporated. ),The title compound was obtained as a colorless oil (8.2 g, 79%)

171504-98-6, As the paragraph descriping shows that 171504-98-6 is playing an increasingly important role.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ¡¤geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

171504-98-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.171504-98-6,Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate,as a common compound, the synthetic route is as follows.

Methyl 1,4-di-tert-butoxycarbonylpiperazine-2-(R)-carboxylate (2.9 g, 8.5 mmol) was dissolved in 4M HCl in dioxane (30 ml) and stirred at room temperature for 30-60 minutes, forming a thick white precipitate. The reaction mixture was concentrated in vacuo and the resulting white solid dried under high vacuum to give methyl piperazine-2-(R)-carboxylate dihydrochloride (1.9 g, 100%). LC/MS Calcd for [M+H]+ 145.1. found 145.1.

The synthetic route of 171504-98-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SYMPHONY EVOLUTION, INC.; US2011/82114; (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.171504-98-6,Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate,as a common compound, the synthetic route is as follows.

LiHMDS (9.9 mL of 1 M, 9.9 mmol) was added to a solution of 1,4-di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (2.0 g, 5.8 mmol) in THF (30 mL) at -78 C under N2. After 45 minutes, iodomethane (615 muL, 9.9 mmol) in THF (5 mL) was added slowly. The mixture was allowed to warm slowly to ambient temperature and stirred overnight. The reaction mixture was partitioned between DCM and saturated aqueous NH4Cl solution. The organic phase was dried, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, DCM/MeOH elution) to give 1,4-di-tert-butyl 2-methyl 2-methylpiperazine-1,2,4- tricarboxylate as a colourless oil (1.5 g, 72%); MS m/z: 359 (M+H)+

171504-98-6, The synthetic route of 171504-98-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

171504-98-6, Methyl 1,4-Bis(Boc)-2-piperazinecarboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step P: di-tert-butyl 2-(hydroxymethyl)piperazine-l,4-dicarboxylate 27. To a solution of 1 ,4- di-tert-butyl 2-methyl piperazine-l ,2,4-tricarboxylate (26; 2 g, 56 mmol) in ethanol (10 mL) was added CaCl2 (5 g, 45 mmol) at 0C, followed by NaBFL (1.1 g, 28 mmol) in two portions. The reaction mixture was warmed to room temperature and stirred for 1.5 h. After cooling to 0C, the mixture was quenched with aq. citric acid solution (6 g citric acid in 50 mL of water). The resulting mixture was then extracted with ethyl acetate (200 mL), and the organic layer was washed with brine, dried over anhy. Na2SC>4, filtered, and concentrated in vacuo to give 1.8 g of the crude title compound as a white solid.

171504-98-6, As the paragraph descriping shows that 171504-98-6 is playing an increasingly important role.

Reference£º
Patent; AGIOS PHARMACEUTICALS, INC.; CAO, Sheldon; POPOVICI-MULLER, Janeta; SALITURO, Francesco G.; SAUNDERS, Jeffrey; TAN, Xuefei; TRAVINS, Jeremy; YAN, Shunqi; YE, Zhixiong; WO2012/171506; (2012); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics