Category: 129779-30-2

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0266] Step 1: (M)-tert-Butyl cis-4-(7-chloro-6-fluoro-1-(2-isopropyl-4-methylpyridin- 3-yl)-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-4-yl)-3,5-dimethylpiperazine-1- carboxylate. Phosphorous oxychloride (0.072 mL, 0.774 mmol) was added dropwise to a solution of (M)-7-chloro-6-fluoro-1-(2-isopropyl-4-methylpyridin-3-yl)pyrido[2,3- d]pyrimidine-2,4(1H,3H)-dione (Intermediate 72A, 180 mg, 0.52 mmol) and DIPEA (0.14 mL, 0.83 mmol) in acetonitrile (2 mL). This mixture was heated to 80 oC for 3 h. The reaction mixture was cooled to 10C and DIPEA (0.27 mL) was added followed by cis-3,5-dimethyl- piperazine-1-carboxylic acid tert-butyl ester (0.122 g, 0.57 mmol). This mixture was allowed to warm to rt and stirred at rt for 18 h. The mixture was poured into ice-cold satd. NaHCO3 and stirred vigorously for 10 min. EtOAc was added and the mixture was separated. The organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was used directly in the following step.

129779-30-2, 129779-30-2 (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate 10822535, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); 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.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl cis-3,5-dimethylpiperazine-1-carboxylate (Combi-Blocks Inc., San Diego, Calif., USA, 130 g, 580 mmol, 1.0 equiv) and triethylamine (100 mL, 700 mmol, 1.2 equiv) in tetrahydrofuran (1250 mL, 10 mL/g) was added acryloyl chloride (56 mL, 700 mmol, 1.2 equiv) at 0 C. The reaction mixture was stirred for 1 h at 0 C. The reaction mixture was diluted with ethyl acetate (2.0 L) and washed with water (2*500 mL). The organic layer was washed with 1 N aqueous HCl (500 mL), saturated NaHCO3 (500 mL), and brine (500 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was adsorbed to a plug of silica gel and purified by silica gel column chromatography (30-40% EtOAc/hexane) to provide the title compound as off-white solid (140 g, 91%). MS (ESI, +ve ion) m/z: 269.0 [M+1]; 1H NMR (400 MHz, DMSO-d6) delta 6.78-6.72 (ddd, J=16.7, 10.4, 1.5 Hz, 1H), 6.15-6.11 (dt, J=16.6, 1.9 Hz, 1H), 5.70-5.67 (dt, J=10.6, 1.9 Hz, 1H), 4.35-4.25 (m, 2H), 3.82 (d, J=12.5 Hz, 2H), 3.01-2.95 (m, 2H), 1.43-1.42 (d, J=1.6 Hz, 9H), 1.19-1.14 (m, 6H).

129779-30-2, 129779-30-2 (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate 10822535, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); 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.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a 20 mL microwave reactor vial was added (3R,5S)-tert-butyl 3,5-dimethylpiperazine- 1 -carboxylate (250 mg, 1.1 67mmol), 1,3 -dibromo-5 -fluorobenzene(592 mg, 2.333 mmol), C52CO3 (950 mg, 2.92 mmol) and toluene (4 mL). The vessel was purged and degassed with N2, then 2,2?-bis(diphenylphosphino)- 1,1 ?-binaphthalene(109 mg, 0.175 mmol) and palladium(II) acetate (52.4 mg, 0.23 3 mmol) were added. The reaction vessel was purged and degassed again. The reaction vessel was capped and the mixture was stirred at 110 C overnight. The reaction mixture was filtered and washed with MeOH and then solvent was removed. The crude was diluted with EtOAc (20 mL),and washed with H20 (20 mL). The orange organic layer was washed with brine, dried over with MgSO4, then concentrated to give crude tert-butyl 4-(3-bromo-5-fluorophenyl) piperazine-1-carboxylate, which was then dissolved in 20% TFA in DCM. The mixture was stirred for 2 hours, concentrated, and then purified by SCX resin (CUBCX1-HL (Benzenesulfonyl, H.L. Resin, 5 g) to provide 1 -((cis)-4-(3 -bromo-5 -fluorophenyl)-3 ,5-dimethylpiperazine, which used directly for next step. LCMS (M+H) = 287.1, 289.1 (1:1 ratio).

129779-30-2, As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (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.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of (3R,55)-tert-butyl 3,5-dimethylpiperazine-1 -carboxylate (2 g, 9 mmol) in DMF (20 mL) was added benzyl (2-bromoethyl)carbamate (3.2 g, 11 mmol), K2C03 (2.5 g,18 mmol) and Nal (1.0 g). The reaction was stirred at 70-80 C for 24 h, cooled to room temperature, and poured into water (60 mL). The reaction mixture was extracted with ethyl acetate, and the organic layers were combined, washed with brine, dried (Na2504), filtered, and evaporated. The crude residue was chromatographed (silica gel, DCM : MeOH = 20: 1) to afford (3R,5 5)-tert-butyl 4-(2-(((benzyloxy)carbonyl)amino)ethyl)-3 ,5 -dimethylpiperazine- 1-carboxylate as a yellow oil (2.2 g, 60%)., 129779-30-2

As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference£º
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth A.; VERNER, Erik; WO2014/182829; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

148 6-((3R.5SV3.5-Dimethyl-4-thiazol-2-ylmethyl-rhoirhoerazin-l-ylmethvn-2-(lH- indazol-4-yl)-4-morpholin-4- yl-thieno [3.2-d]p yrimidine.Via 2-chloro-6-((3R,5 S)-3 ,5 -dimethyl-4-thiazol-2-ylmethyl-piperazin- 1 – ylmethyl)-4-mophiholin-4-yl-thieno[3,2-d]pyrimidine, prepared from (2R,6S)-2,6- dimethyl- 1 -thiazol-2-ylmethyl-piperazine.Amine preparation: 2-Thiazolecarboxaldehyde was converted to the corresponding alcohol by treatment with sodium borohydride. Reaction with methanesulfonyl chloride yielded methanesulfonic acid thiazol-2-ylmethyl ester. A mixture of methanesulfonic acid thiazol-2-ylmethyl ester (393mg), (3R,5S)-3,5- dimethyl-piperazine-1 -carboxylic acid tert-butyl ester (described previously, 435mg), potassium carbonate (309mg) and tetrabutyl ammonium iodide (827mg) was heated to reflux in MeCN (1OmL). After 4 days the reaction mixture was cooled, diluted with ethyl acetate, washed with water and dried (MgSO4). The solvent was evaporated and the residue purified by flash chromatography to give (R)-3,5- dimethyl-4-thiazol-2-ylmethyl-piperazine-l -carboxylic acid (S) -tert-butyl ester (314mg). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt. EPO 1H NMR (400MHz, CDCl3) 1.12 (d, J=6.0Hz, 6H), 2.06 (m, 2H), 2.85 (m, 4H), 3.80 (s, 2H), 3.92 (m, 4H), 4.09 (m, 4H), 4.17 (s, 2H), 7.24 (d, J=3.2Hz, IH), 7.38 (s, IH), 7.51 (m, IH), 7.59 (d, J=8.3Hz, IH), 7.74 (d, J=3.3Hz, IH), 8.29 (d, J=7.3Hz, IH), 9.03 (s, IH), 10.1 (br s, IH); MS (ESf) 561 (MH+)., 129779-30-2

As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference£º
Patent; PIRAMED LIMITED; WO2006/46031; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tert-butyl (3S, 5R)-3,5-dimethylpiperazine-1-carboxylate (1 g, 4.67 mmol, 1 eq) and ethyl 2-bromoacetate (701 mg, 4.20 mmol, 0.9 eq) in acetonitrile (10 mL) was added diisopropyl ethyl amine (1.81 g, 14.00 mmol, 3 eq). The reaction mixture was stirred at 80C for 12 hours. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3). The combined organic layers were washed with brine (80 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Petroleum ether/Ethyl acetate=30/1 to 1/1). tert-butyl (3S,5R)-4-(2-ethoxy-2-oxo-ethyl)-3,5-dimethyl-piperazine-1-carboxylate (1.09 g, 3.63 mmol, 77% yield) was obtained as a white solid. LC/MS (ESI) m/z: 301.1 [M+1] +; 1H-NMR (400MHz, CDCl3) d 4.16 (q, J=7.2 Hz, 2H), 4.02 – 3.72 (m, 2H), 3.56 (s, 2H), 2.96 – 2.82 (m, 2H), 2.53 (s, 2H), 1.46 (s, 9H), 1.27 (t, J=7.2 Hz, 3H), 1.08 (d, J=6.4 Hz, 6H).

129779-30-2, As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference£º
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; DONG, Hanqing; QIAN, Yimin; ZIMMERMAN, Kurt; (1451 pag.)WO2020/51564; (2020); 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.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of (3S ,5R)-tert-butyl 3,5 -dimethylpiperazine- 1 -carboxylate (2.1 4g, 10.0 mmol), 3-bromopropan-1-ol (2.76 g, 20 mmol) and K2C03(2.76 g, 20 mmol) in DMF (5.0 mL) was heated to 90C for 2 h in a microwave. The reaction mixture was poured into water (30 mL) and extracted with EtOAc. The organic phase was separated, dried and concentrated. The residue was purified by chromatography (DCM:MeOH=30: 1) to provide (3R,5S)-tert-butyl 4-(3- hydroxypropyl)-3 ,5 -dimethylpiperazine- 1 -carboxylate as a yellow liquid (2.1 4g, 50%)., 129779-30-2

129779-30-2 (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate 10822535, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; PRINCIPIA BIOPHARMA, INC.; VERNER, Erik; BRAMELD, Kenneth Albert; WO2015/120049; (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.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

A stirred solution of (3S,5R)-tert-butyl 3,5- dimethylpiperazine-1 -carboxylate (20 g, 93.0 mmol, 1 eq) in LiHMDS (200 mL) was cooled to 0C and 2,6-difluoropyridine (26.8 mL, 280.3 mmol, 3 eq), and xanthophos (3.24 g, 5 mmol, 0.06 eq) were added followed by Pd2(dba)3 (2.5 g, 2.7 mmol, 0.03 eq). Then, the resultant reaction mixture was stirred overnight at 80C. The reaction was monitored with TLC, and TLC indicated formation of a non-polar spot. The reaction mixture was quenched with ice water (100 mL), filtered through celite and washed with ethyl acetate. The layers were separated, and the aqueous layer extracted with ethyl acetate (2×150 mL) and washed with brine solution (1×100 mL). The combined organic layer was dried over Na2S04, and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography (silica gel, 100-200 mesh) using 0-5% ethyl acetate in petroleum ether as an eluent to afford (3R,5S)-tert-butyl 4-(6-fluoropyridin-2-yl)-3,5-dimethylpiperazine-1 -carboxylate (20 g, 37.73% yield) as a brown liquid. LCMS: m/z 310.54 (M+H).

129779-30-2, The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; (191 pag.)WO2019/119145; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

129779-30-2, (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

At 100mLAdd in three bottlescis-3,5-Dimethylpiperazine-1-carboxylic acid tert-butyl ester (2 g, 9.34 mmol),Pyridine (1.47 g, 18.6 mmol) and DCM (10 mL), cooled to 0 C,A solution of allyl chloroformate (1.68 g, 14 mmol) in DCM was added dropwise.The reaction was allowed to warm to room temperature overnight.The reaction system was added with water (20 mL) and allowed to stand for stratification.The organic phase was concentrated to give a crude product. The crude product was purified by column chromatography.Eluent: PE/EA=5/1, collect product,Concentrated under reduced pressure to give 1.2 g of colorless oil.Yield: 43.2%.

129779-30-2, As the paragraph descriping shows that 129779-30-2 is playing an increasingly important role.

Reference£º
Patent; Beijing Purunao Bio-technology Co., Ltd.; Zhang Peilong; Shi Hepeng; Lan Wenli; Song Zhitao; (250 pag.)CN108707139; (2018); 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.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

The 5 – ((2,4-dioxo -3,4-dihydrochinazolines having antiviral properties -1 (2H)-yl) methyl) – 2-fluoro-benzoic acid (100 mg, 0 . 16mmol), EDCI (124 mg, 0 . 64mmol), HOBt (88 mg, 0 . 64mmol) and TEA (66 mg, 0 . 64mmol) into the reaction bottle in, addition of about 2 ml of the dissolution of water-free DMF, r.t. The lower stirring 60 min, then dropwise (3S, 5R) – 3,5-dimethyl piperazine-1-carboxylic acid T-butyl ester (104 mg, 0 . 48mmol) in the DMF solution to the reaction solution, r.t. The lower stirring overnight, the reaction solution is poured into 100 ml water, using 100mLDCM extraction, an organic layer for sequentially 1MHCl (100 ml), saturated NaCl (100 ml) and water (100 ml) washing, vacuum concentration, silica gel column chromatography, to obtain 59 mg solid, yield 36.3%.

129779-30-2, 129779-30-2 (3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate 10822535, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Institute Of Materia Medica Chinese Academy Of Medical Sciences; Xu, Bailing; Chen, Xiaoguang; Yao, Haiping; Ji, Ming; Jin, Jing; Zhou, Jie; Wang, Ke; Zhao, Dalong; (55 pag.)CN105461697; (2016); A;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics