Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1030377-21-9,(S)-1-Boc-2-(Hydroxymethyl)piperazine,as a common compound, the synthetic route is as follows.

A mixture of (S)-tert-butyl 2-(hydroxymethyl)piperazine-l -carboxylate (602.7 mg, 2.79 mmol) and (S)-2-methoxyoxirane (308.9 mg, 3.4 mmol) in ethanol (10 mL) was heated at 120 C for 30 min using microwave. The mixture was concentrated to dryness. The residue was purified with flash column chromatography on silica gel using 1 -10% methanol in dichloromethane to afford a oil as the product (794.6 mg) in 94% yield. NMR (500 MHz, Chloroform-*/) delta 4.11 (br, 1H), 3.93 – 3.80 (m, 2H), 3.41 (dd, J = 9.7, 3.7 Hz, 1H), 3.36 (s, 3H), 3.33 (dd, J = 9.7, 6.0 Hz, lH), 3.25 (br, 2H), 3.06 (d, J = 1 1.6 Hz, 1H), 2.89 (br, 2H), 2.79 (d, J = 1 1.2 Hz, 1H), 2.47 (dd, J = 12.7, 9.1 Hz, 1H), 2.49 – 2.33 (m, 1 H), 2.30 – 2.21 (m, 2H), 1.43 (s, 9H). MS for C,4H28N205: 305.2 (MH+).

1030377-21-9, As the paragraph descriping shows that 1030377-21-9 is playing an increasingly important role.

Reference£º
Patent; NEKTAR THERAPEUTICS (INDIA) PVT. LTD.; NEKTAR THERAPEUTICS; SHARMA, PANKAJ; KHATRI, VIJAY KUMAR; GU, XUYUAN; SONG, YUAN; SHEN, MICHAEL LIXIN; SAUTHIER, JENNIFER RIGGS; ANAND, NEEL K.; KOZLOWSKI, ANTONI; ODINECS, ALEKSANDRS; RILEY, TIMOTHY A.; REN, ZHONGXU; MU. YONGQI; SHEN, XIAOMING; YUAN. XUEJUN; AURRECOECHEA, NATALIA; O’MAHONY, DONOGH JOHN ROGER; WO2015/92819; (2015); A2;,
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.373608-48-1,tert-Butyl 4-(3-aminopropyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a 50 mL RBF was added tert-butyl 4-(3-aminopropyl)piperazine-1-carboxylate (1.105 g, 4.54 mmol), DCE (Volume: 10.32 ml), 3-methylpicolinaldehyde (.5 g, 4.13 mmol) and STAB-H (1.575 g, 7.43 mmol). The reaction was stirred overnight then diluted with DCM and quenched with 2M NaOH. The organic layer was dried with Na2SO4, filtered and concentrated to a yellow oil which was purified via silica gel chromatography (DCM 2 minutes, 10% B(80:20:3, DCM:MeOH:NH4OH) 5 minutes and 50% B 9 minutes) to afford tert-butyl 4-(3-(((3-methylpyridin-2-yl)methyl)amino)propyl)piperazine-1-carboxylate (0.88 g, 2.53 mmol, 61 % yield).1H NMR (400 MHz, CDCl3): delta = 8.37 (d, J= 5.0 Hz, 1H), 7.42 (d, J= 7.3 Hz, 1H), 7.07 (dd, J= 7.6, 4.8 Hz, 1H), 3.88 (s, 2H), 3.43 (t, J= 5.2 Hz, 4H), 2.79 (t, J= 6.8 Hz, 2H), 2.45 (t, J= 7.2 Hz, 2H), 2.39 (t, J= 5.2 Hz, 4H), 2.30 (s, 3H), 1.78 (pent, J= 7.0 Hz, 2H), 1.45 (s, 9H);, 373608-48-1

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

Reference£º
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (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.30459-17-7,1-(4-Trifluoromethylphenyl)piperazine,as a common compound, the synthetic route is as follows.

General procedure: A 5.0 mL round-bottomed flask was equipped with a reflux condenser, 2.5 mol % chloro(1,5-cyclooctadiene)iridium (I) dimer [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP were added and followed by addition of anhydrous tetrahydrofuran (2.0 mL). After they were stirred for 10 min to produce a yellow solution. 1,4-Dihydro-1,4-epoxynaphthalene 1a (50 mg, 0.3468 mmol) was added; then 10 min later, additive of ammonium iodide (1.0 equiv. to 1a) was added and heated to reflux. At the first sign of reflux, N-substituted piperazine nucleophiles (2.0 equiv. to 1a) were added. The reaction mixture was stirred at reflux and monitored by TLC until completion (typically 6-12 h). The solvent was removed in vacuo and the crude mixture was purified by column chromatography on silica gel to afford the desired products., 30459-17-7

The synthetic route of 30459-17-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yang, Wen; Luo, Renshi; Yang, Dingqiao; Molecules; vol. 20; 12; (2015); p. 21103 – 21124;,
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.304897-49-2,tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.,304897-49-2

To a solution of 2,4-dihydroxy-5-isopropyl-benzenecarbodithioic acid (3.20 g, 14.0 mmol) in DMF (50 mL) was added sodium 2-chloroacetate (2.61 g, 22.4 mmol) and sodium carbonate (4.45 g, 42.0 mmol), and the solution degassed by bubbling nitrogen through the solution. The mixture was stirred at room temperature for 3 h, then a solution of tert-butyl 4-(4-aminobenzyl)piperazine-l-carboxylate (4.08 g, 14.0 mmol) in DMF (10 mL) was added. The resulting mixture was stirred at 80 C for 3 h. The reaction mixture was poured into ice water, and extracted with ethyl acetate (3 x 100 ml). The combined organic layers were washed with brine, dried with sodium sulfate, and the solvent removed in vacuo to give 3A (5.20 g, 10.7 mmol, 76% yield).

The synthetic route of 304897-49-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TARVEDA THERAPEUTICS, INC.; CIPRIANI, Tyler; MOREAU, Benoit; BILODEAU, Mark T.; QUINN, James M.; WOOSTER, Richard; CIRELLO, Amanda L.; PERINO, Samantha; WHALEN, Kerry; KADIYALA, Sudhakar; WHITE, Brian H.; (172 pag.)WO2019/118830; (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.502649-32-3,1-Boc-3-Isopropylpiperazine,as a common compound, the synthetic route is as follows.

Exchanging 2,4-dichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine and phenylboronic acid for 2-(4-(methoxymethyl)phenyl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane, the first step of Example 137 was used to prepare 2-chloro-5-fluoro-4-(4- (methoxymethyl)phenyl)pyrimidine. To a stirred solution of this intermediate (0.400 g, 1.58 mol) in toluene (8 mL) was added tert-butyl 3-isopropylpiperazine-l-carboxylate (0.434 g, 1.90 mmol), bis(tri-tert-butylphosphine)palladium(0) (0.081 g, 0.158 mmol), trimethylhexadecylammonium chloride (0.101 g, 0.316 mmol) and a 50% aqueous sodium hydroxide solution (0.25 mL, 4.73 mmol). The mixture was heated at 100 C overnight and concentrated. The residue was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford partially purified tert-butyl 4-(5-fluoro-4-(4- (methoxymethyl)phenyl)pyrimidin-2-yl)-3 -isopropylpiperazine- 1 -carboxylate as light yellow oil (0.500 g). This material was taken up in dichloromethane (5 mL), stirred and treated with trifluoroacetic acid (3.0 mL). After 3 hours, the reaction was concentrated and the residue was purified by reversed-phase flash chromatography over CI 8 silica using a acetonitrile/water/trifluoroacetic acid eluant. 5-Fluoro-2-(2-isopropylpiperazin-l- yl)-4-(4-(methoxymethyl)phenyl)pyrimidine was afforded as a light yellow oil (0.200 g, 36% for two steps). Using General Procedure A and Intermediate 5, this intermediate was used to generate the title compound as a white solid (0.105 g, 63%). 1H NMR (500 MHz, CDCls) delta 8.24 (d, J = 3.5 Hz, 1H), 8.08 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 4.75-4.72 (m, 1H), 4.59-4.55 (m, 3H), 4.33-4.31 (m, 1H), 3.94-3.86 (m, 2H), 3.45 (s, 3H), 3.28-3.19 (m, 2H), 3.07-2.85 (m, 7H), 2.43-2.40 (m, 1H), 2.26-2.19 (m, 1H), 1.94-1.50 (m, 9H), 1.13 (t, J = 7.5 Hz, 3H), 0.87 (d, J = 7.5 Hz, 3H) ppm. 13C NMR (125 MHz, CDCI3) delta 158.4, 157.0, 151.1, 151.0, 150.4, 148.4, 146.7, 146.4, 140.9, 133.4, 129.0, 128.9, 127.5, 74.2, 59.0, 58.3, 57.5, 57.3, 53.2, 47.8, 47.6, 46.4, 46.1, 44.0, 43.9, 43.5, 43.3, 39.9, 39.7, 39.1, 36.7, 36.4, 27.1, 27.0, 25.9, 25.7, 24.4, 24.1, 20.4, 20.2, 19.1, 19.0 ppm. Purity: > 99% LCMS (214 nm & 254 nm); retention time 1.54 min; (M+H+) 525.3., 502649-32-3

As the paragraph descriping shows that 502649-32-3 is playing an increasingly important role.

Reference£º
Patent; GENZYME CORPORATION; BOURQUE, Elyse; CABRERA-SALAZAR, Mario, A.; CELATKA, Cassandra; CHENG, Seng, H.; HIRTH, Bradford; GOOD, Andrew; JANCSICS, Katherine; MARSHALL, John; METZ, Markus; SCHEULE, Ronald, K.; SKERLJ, Renato; XIANG, Yibin; ZHAO, Zhong; LEONARD, John; NATOLI, Thomas; MAKINO, Elina; HUSSON, Herve; BESKROVNAYA, Oxana; WO2014/43068; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

502649-32-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.502649-32-3,1-Boc-3-Isopropylpiperazine,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl 3-isopropylpiperazine-1-carboxylate (830 mg, 3.6 mmol) and 2-chloroquinaxaline (600 mg, 3.6 mmol) in dimethyl sulfoxide (5 mL), cesium fluoride (550 mg, 3.6mmol) was added. The reaction mixture was stirred at 60 oc for 30 hours, and then the reactionmixture was poured into water (70 mL) and extracted with diethyl ether (2×20 mL). The crudeproduct was purified by silica gel column chromatography eluting with mixture hexane:ethyl acetate10 (4:1) to afford 600 mg, 46% of the titled compound as a light-yellow solid. 1H NMR (300 MHz,15DMSO-d6) o ppm 0.84-0.90 (m, 3H), 1.16-1.25 (m, 3H), 1.50 (s, 9H), 2.20-2.30 (m, 1H), 3.00-3.12(m, 2H), 3.20-3.28 (m, 1H), 4.17-4.23 (m, 1H), 4.30-4.36 (m, 1H), 4.55-4.65 (m, 1H), 7.55-7.62 (m,1H), 7.72-7.78 (m, 1H), 7.85-7.90 (m, 1H), 8.15-7.23 (m, 1H), 8.58 (s, 1H).

The synthetic route of 502649-32-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBVIE INC.; GOMTSIAN, Artour; DEKHTYAR, Tatyana; FRANK, Kristine E.; FRIEDMAN, Michael M.; JOSEPHSOHN, Nathan; MOLLA, M-Akhteruzz; VASUDEVAN, Anil; NG, Teresa; SHAFEEV, Mikhail; WO2014/5129; (2014); 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.30459-17-7,1-(4-Trifluoromethylphenyl)piperazine,as a common compound, the synthetic route is as follows.

5-Phenylpentanoic acid (105 mg, 0.59 mmol), HOBt (87 mg, 0.65 mmol), TBTU (208 mg, 0.65 mmol), anhydrous triethylamine (131 ??_, 0.94 mmol) and anhydrous DMF (2 mL) were placed in an oven-dried Schlenk tube under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes. A second Schlenk tube was prepared containing 1-(4- (trifluoromethyl)phenyl)piperazine (150 mg, 0.65 mmol) and anhydrous DMF (1 mL) under a nitrogen atmosphere. The resulting solution was stirred until complete dissolution of the piperazine had occurred. The piperazine solution was then transferred, via a cannula, to the first Schlenk tube containing the carboxylic acid. The resulting solution was stirred under nitrogen and monitored by TLC. After 24 hours, the DMF was removed under reduced pressure and the resulting oil was acidified using a 0.1 M HCI solution. The aqueous mixture was extracted with DCM (20 mL, followed by 4 x 10 mL) and the organic layer washed with a saturated sodium bicarbonate solution (3 x 20 mL) and brine (3 x 20 mL). The organic layer was dried over magnesium sulphate and the solvent removed in vacuo. The residue was purified using flash chromatography (3:2, EtOAc:n-hexane) to obtain the desired product in an 44 % yield. H NMR (300 MHz, CDCI3) ? 7.50-7.46 (m, 2H), 7.29- 7.14 (m, 5H), 6.91-6.87 (m, 2H), 3.74 (d, J = 4.5 Hz, 2H), 3.55 (d, J = 4.5 Hz, 2H), 3.20 (d, J = 3.6 Hz, 4H), 2.63 (d, J = 4.8 Hz, 2H), 2.35 (d, J = 4.8 Hz, 2H), 1.68 (d, J = 4.5 Hz, 4H). 3C NMR (75 MHz, CDCI3) 171.5, 152.9, 142.1 , 128.4, 128.3, 126.4 (q, J = 3 Hz), 125.8, 120.6 (q, J = 33 Hz), 1 19.2 (q, J = 271.5 Hz), 1 14.9, 48.3, 48.1 , 45.1 , 41.1 , 35.7, 33.1 , 31.1 , 24.8. MS (+ESI) calcd for C22 H25 F3 N2 O m/z: [M + Na]+, 413.181 1 ; found 413.1794 [Diff(ppm) = – 4.08].

30459-17-7, 30459-17-7 1-(4-Trifluoromethylphenyl)piperazine 121718, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; NATIONAL UNIVERSITY OF IRELAND, MAYNOOTH; STEPHENS, John; FINDLAY, John; KINSELLA, Gemma; MARTIN, Darren; DEVINE, Robert; VELASCO-TORRIJOS, Trinidad; WO2013/60860; (2013); 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.192130-34-0,tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Cat. TsOH monohydrate was added to a suspension of methyl 14′-cyclohexyl-2,2- dimethylspiro[l,3-dioxane-5,7′-indolo[l,2-e][l,5]benzoxazocine]-H’-carboxylate in MeOH/THF 1:2 (0.03 M), and the solution was stirred at RT for 3 h. Filtration on a pad of neutral alumina using EtOAc as eluent afforded after evaporation of the solvent in vacuo methyl 14-cyclohexyl- 7, 7-bis(hydroxymethyl)-7,8-dihydro-6H-indolo[l,2-e][l,5]benzoxazocine- 11 -carboxylate (quant). This material was dissolved in dry MeCN (0.2M) and DIPEA (4.0 eq) and trifluoromethane sulfonic anhydride (3.5 eq) was added at 0 0C. The mixture was stirred at 0 0C for 15 min, then more DIPEA (4 eq) was added at RT. 7ert-butyl 4-(2-aminoethyl)piperazine-l- carboxylate (2 eq) was added, and the mixture was stirred at 70 0C for 1 h. After removal of the solvent in vacuo EtOAc was added, the solution was washed with H2O and brine, dried over Na2SO4 and the solvent was removed in vacuo. The crude methyl \-{2-[4-(tert- butoxycarbonyl)piperazin- 1 -yljethyl} – 14′-cyclohexylspiro[azetidine-3 ,7′-indolo[ 1 ,2- e][l,5]benzoxazocine]-l l’-carboxylate was taken in DCM/TFA 3:1 (0.13M) and stirred at RT for 2 h. The mixture was evaporated to dryness and the residual material was dissolved in EtOAc. The solution was washed with sat. aq. NaHCO3 and brine. The organic phase was dried overNa2SO4 and the solvent evaporated in vacuo. The residue was dissolved in dry dioxane (0.06M) and sulfamide (5 eq) was added. The mixture was stirred at reflux for 3 h, then overnight at RT. The residue obtained after evaporation was purified by FC (EtOAc/MeOH, 9:1) to afford the title compound in 40percent yield. (ES+) m/z 622 (M+H)+., 192130-34-0

As the paragraph descriping shows that 192130-34-0 is playing an increasingly important role.

Reference£º
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2009/10783; (2009); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

57260-70-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57260-70-5,tert-Butyl 4-benzylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

The mixture of haloalkyl-5-benzhydryl-1H-tetrazole, 10a(300 mg, 1 mmol), alkylpiperazine, 13a (264, 1.5 mmol), K2CO3(276 mg, 2 mmol), NaI (catalyst) and CH3CN (15 mL) was refluxed. After the completion, reaction mixture was cooled, filtered and concentrated. The obtained product was purified by column chromatographyon silica gel with n-hexane: EtOAc: MeOH (10:1.5:0.5)to obtain 2a (131 mg, 30%) as light brown liquid. Rf = 0.56 (n-hexane:EtOAc: MeOH = 2.5:1.5:1). 1H NMR (500 MHz, CDCl3): d 7.35-7.24 (m, 15H), 5.84 (s, 1H), 4.72-4.69 (m, 2H), 3.49 (s, 2H), 3.04-2.97 (m, 2H), 2.53-2.42 (m, 8H); 13C NMR (125 MHz, CDCl3): d167.7, 140.9, 138.0, 129.2, 128.8, 128.6, 128.2, 127.1, 127.0, 63.0,56.4, 52.9, 52.8, 50.5, 48.6.

As the paragraph descriping shows that 57260-70-5 is playing an increasingly important role.

Reference£º
Article; Paudel, Suresh; Acharya, Srijan; Yoon, Goo; Kim, Kyeong-Man; Cheon, Seung Hoon; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2266 – 2276;,
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.259808-67-8,1-Boc-3,3-Dimethylpiperazine,as a common compound, the synthetic route is as follows.

tert-butyl 3,3-dimethylpiperazine-1-carboxylate (19.90 g, 92.86 mmol) and (2,2- dimethylpiperazin-1-yl)methanone hydrochloride (Intermediate C) (27.87 g, 84.60 mmol) are dissolved in DMF (300 mL) before HATU (35.45 g, 93.23 mmol) and DIPEA (27.72 g, 37.36 mL, 214.5 mmol) are added. The solution is stirred at room temperature for 3h, and then water is added dropwise. The aq. phase is extracted three times with EtOAc. The combined organic phase is washed with water and brine. The organic phase is then dried over Na2SO4, filtered and the filtrate evaporated under reduced pressure. The crude product is purified passing through a pad of silica gel (25%-33% EtOAc/hexanes affording the title product (34.28 g, 91% yield) as a yellow orange foamy solid, which is used directly in the next step. 1H NMR (400 MHz, Chloroform-d) 6 7.34 (s, 1H), 7.06 (s, 1H), 3.84 (dd, J = 6.6, 4.8 Hz, 2H), 3.67 – 3.45 (m, 4H), 2.71 (tt, J = 10.3, 5.5 Hz, 1H), 1.85 – 1.77 (m, 4H), 1.77 – 1.71 (m, 1H), 1.57 – 1.51 (m, 2H), 1.49 (s, 9H), 1.49 (s, 9H), 1.43- 1.31 (m, 3H), 1.01 (s, 3H), 0.97 (s, 3H). ESI-MS m/z calc. 525.3567, found 526.61 (M+1) Retention time: 3.15 minutes using method A.

259808-67-8, The synthetic route of 259808-67-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LIU, Bingcan; DORICH, Stephane; DE LESELEUC, Mylene; DUPONT-GAUDET, Kristina; JAMES, Clint, Alwyn; VAILLANCOURT, Louis; BEAULIEU, Marc-Andre; STURINO, Claudio; (236 pag.)WO2018/57588; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics