Heterocyclic Building Blocks-piperazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.325145-35-5,(S)-tert-Butyl 2-ethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

(8D) Tert-butyl (2S)-4-{4-[{[trans-4-(4-fluorophenoxy)cyclohexyl]carbonyl}(methyl)amino]-2-methylbenzyl}-2-ethylpiperazine-1–carboxylate [0230] Trans-4-(4-fluorophenoxy)-N-(4-formyl-3-methylphenyl)-N-methylcyclohexanecarboxamide (55.0 mg, 0.149 mmol) produced in (8C) and tert-butyl (2S)-2-ethylpiperazine-1-carboxylate (39.0 mg, 0.182 mmol) were dissolved in dichloromethane (3 mL), and acetic acid (45.0 mg, 0.749 mmol) was added thereto at room temperature, and then, sodium triacetoxy borohydride (48 mg, 0.226 mmol) was added thereto at 0¡ãC. Then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. [0231] To the reaction solution, a saturated aqueous solution of sodium hydrogen carbonate was added, and the organic matter was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate = 100:0 to 0:100 (v/v)), whereby the target compound was obtained as a colorless oil (70.0 mg, yield: 83percent). 1H-NMR (CDCl3, 400MHz): delta0.78 (3H, t, J = 7.6 Hz), 1.19-1.05 (2H, m), 1.46 (9H, s), 1.82-1.58 (6H, m), 2.16-2.02 (4H, m), 2.28-2.18 (1H, m), 2.38 (3H, s), 2.77-2.64 (2H, m), 3.08-2.96 (1H, m), 3.23 (3H, s), 3.48-3.35 (2H, m), 4.13-3.82 (3H, m), 6.80-6.74 (2H, m), 6.98-6.88 (4H, m), 7.29 (1H, d, J = 7.4 Hz)., 325145-35-5

As the paragraph descriping shows that 325145-35-5 is playing an increasingly important role.

Reference£º
Patent; Daiichi Sankyo Company, Limited; TODA, Narihiro; TAKANO, Rieko; SHIDA, Takeshi; KATAGIRI, Takahiro; IWAMOTO, Mitsuhiro; ASHIDA, Shinji; YAMAZAKI, Mami; EP2623492; (2013); A1;,
Piperazine – Wikipedia
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74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,74879-18-8

Example 24 2-(2,8-dimethylimidazo[l,2-b]pyridazin-6-yl)-9-methyl-7-[(3S)-3-methylpiperazin-l- yl]pyrido[l,2-a]pyrimidin-4-one In a sealed tube, 2-(2,8-dimethylimidazo[l,2-b]pyridazin-6-yl)-7-fluoro-9-methyl- pyrido[l,2-a]pyrimidin-4-one (Intermediate 4; 50 mg, 0.155 mmol) and (S)-2-methylpiperazine (62 mg, 0.619 mmol, 4.0 eq.) were stirred in DMSO (2 mL) at 125C overnight. The solvent was removed under high vacuum. The residue was taken up in CH2CI2 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 (S1O2, CH2Cl2/MeOH=95/5 to 90/10) to afford the title product (45 mg, 72%) as a light yellow solid. MS m/z 404.3 [M+H+].

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

Reference£º
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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21043-40-3, 1-Cyclopentylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 35; (4-Cyclopentyl-piperazin-1-yl)-[4-(2-fluoro-phenylamino)-cyclohexyl]-methanone; A mixture of 86 mg (0.5 mmol) 4-oxo-cyclohexanecarboxylic acid ethyl ester (commercially available), 100 mg (0.6 mmol) 2-fluoro-phenylamine and 300 mg (5 mmol) acetic acid in 5 mL THF was stirred for 1 h at 60 C. Afterwards 159 mg (0.75 mmol) sodium triacetoxyborohydride were added and the mixture was heated to 65 C. for 16 h. After evaporation of the volatiles 10 mL 1N NaHCO3 aq. was added and the mixture was extracted with DCM. The combined organic layers were evaporated and methanol and DMF were added and the mixture was subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.1% NEt3). The combined product fractions were evaporated to dryness to yield the intermediate 3-(2-fluoro-phenylamino)-cyclohexanecarboxylic acid ethyl ester. MS(m/e): 266.2 (MH+). A mixture of 21 mg (0.08 mmol) 4-(2-fluoro-phenylamino)-cyclohexanecarboxylic acid ethyl ester, 17 mg (0.4 mmol) LiOH.H2O in a mixture of 2 mL THF/methanol/water was heated to 45 C. for 2 h and subsequently evaporated. The intermediately built acid was dissolved in 2 mL DMF and treated with 30 mg (0.096 mmol) TBTU, 24 mg (0.24) NEt3 and 13.5 mg (0.88 mmol) 1-cyclopentyl-piperazine (commercially available) and stirred for 16 h at room temperature. The mixture was directly subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.1% NEt3). The combined product fractions were evaporated to dryness to yield 6.4 mg (21%) of the title compound. MS(m/e): 374.4 (MH+)., 21043-40-3

As the paragraph descriping shows that 21043-40-3 is playing an increasingly important role.

Reference£º
Patent; Nettekoven, Matthias; Plancher, Jean-Marc; Roche, Olivier; Takahashi, Tadakatsu; Taylor, Sven; US2007/167436; (2007); A1;,
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129799-08-2, 1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 1 -(tert-butyl) 3-methyl piperazine-1 ,3-dicarboxylate (CAS Number 129799-08-2; 0.500 g, 2.05 mmol) in DMF (10 ml) was added TEA (0.300 ml, 2.670 mmol) at 0C. Methanesulphonyl chloride (0.300 g, 2.67 mmol) was added dropwise to the reaction mixture at 0C, warmed to rt and stirred for 4 h. The resulting reaction mixture was poured into water (40 ml) and extracted with EtOAc (2 x 30 ml). The combined organic phase was collected, dried over Na2S04, filtered and concentrated under reduced pressure yielding 1 -(tert-butyl) 3-methyl 4- (methylsulfonyl)-piperazine-l ,3-dicarboxylate (0.120 g, 0.372 mmol). This material was used directly for the next step without further purification. LCMS: Method C, 1 .900 min, MS: ES+ 267.30 [M-56]., 129799-08-2

129799-08-2 1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate 2756819, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (167 pag.)WO2018/65768; (2018); A1;,
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70261-82-4, 4-(4-Methylpiperazin-1-ylmethyl)phenylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

70261-82-4, Preparation Example 6 Under an argon atmosphere, a mixture of 3-chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide (50 mg), 4-[(4-methylpiperazin-1-yl)methyl]aniline (48 mg), tris(dibenzylideneacetone)dipalladium (0) (14 mg), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (30 mg), cesium carbonate (101 mg), and dioxane (2 mL) was heated and refluxed for 4 hours. The reaction mixture was cooled and then diluted with ethyl acetate, and the organic phase was washed with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol:28% aqueous ammonia=95:4.5:0.5-90:9:1, chloroform: methanol=1:0-9:1) to obtain 6-ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-5-(3-nitrophenoxy)pyrazine-2-carboxamide (14 mg) as a yellow oily substance.

As the paragraph descriping shows that 70261-82-4 is playing an increasingly important role.

Reference£º
Patent; ASTELLAS PHARMA INC.; Matsuya, Takahiro; Kondoh, Yutaka; Shimada, Itsuro; Kikuchi, Shigetoshi; Iida, Maiko; Onda, Kenichi; Fukudome, Hiroki; Takemoto, Yukihiro; Shindou, Nobuaki; Sakagami, Hideki; Hamaguchi, Hisao; US2014/323463; (2014); A1;,
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Piperazines – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.148546-99-0,3-(4-Methylpiperazin-1-yl)aniline,as a common compound, the synthetic route is as follows.

EXAMPLE 132 Naphthalene-2-sulfonic Acid [3-(4-Methylpiperazin-1-yl)phenyl]amide (E132) The title compound (E132) was prepared from 3-(4-methylpiperazin-1-yl)benzenamine and naphthalene-2-sulfonyl chloride according to the method of Example 1 MH+=382.

148546-99-0, 148546-99-0 3-(4-Methylpiperazin-1-yl)aniline 11564613, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; SmithKline Beecham p.l.c.; US6423717; (2002); B1;,
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, To a stirring suspension of 1-fluoro-4-nitrobenzene (0.60 g, 4.24 mmol) and potassium carbonate (2.34 g, 16.97 mmol) in anhydrous DMF (5 mL) was added (2S,5R)-tert- butyl 2,5-dimethylpiperazine-1-carboxylate (1 g, 4.67mmol) and the mixture heated at 90 C for 120 h. After cooling the mixture was partitioned between brine/water (1:1, 50 mL) and ethyl acetate (25 mL) . The aqueous layer was separated and extracted with ethyl acetate (3 x 25 mL) . The combined ethyl acetate fractions were washedwith brine/water (1:1, 4 x 12.5 mL), dried (anhydrous sodium sulfate), filtered and reduced in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0-50% Ethyl Acetate in Cyclohexane) to afford the title compound (1.03 g, 72.4%) . ?H NMR (400 MHz, CDC13) : 3 8.12 (d, 2H), 6.77 (d,2H), 4.24-4.58 (m, 1H), 4.03-4.16 (m, 1H), 3.73-3.93 (m,1H), 3.31-3.49 (m, 3H), 1.49 (s, 9H), 1.24 (d, 3H), 1.18(d, 3H) . LCMS (Method C) : = 1.80 mm, m/z = 336 [M+H].

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; ALMAC DISCOVERY LIMITED; HARRISON, Timothy; TREVITT, Graham; HEWITT, Peter Robin; O’DOWD, Colin Roderick; BURKAMP, Frank; WILKINSON, Andrew John; SHEPHERD, Steven D.; MIEL, Hugues; WO2015/92431; (2015); 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

To a stirred biphasic solution of (R)-l-Boc-3-hydroxymethylpiperazine (5.00 g, 23.1 mmol) and NaHCC-3 (5.83 g, 69.4 mmol) in ethyl acetate (46.2 ml) and water (46.2 ml) at 0C was added benzyl chloroformate (4.95 ml, 34.7 mmol) dropwise. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with EtOAc (50.0 ml) and the organic layer was separated, dried (Na2S04) and concentrated. The crude product was purified by flash chromatography eluting with 10-50% EtOAc/hexanes gradient to afford the title compound (7.62 g, 21.7 mmol, 94.1%). ESI MS m/z 251.1 [M-Boc+H]+., 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; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
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103-76-4, N-(2-Hydroxyethyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-(piperazin-1-yl)ethan-1-ol (5 g, 38.41 mmol, 1.00 equiv) was dissolved inDCM (100 mL), and a solution of di-tert-butyl dicarbonate (8.38 g,38.40 mmol, 1.00 equiv) in DCM (20 mL) was added drop-wise. The reaction was left under agitation overnight at ambient temperature. The reaction was evaporated to dryness and the residue dissolved in 200 mL of AcOEt, washed 5 times with NaC1 (sat.), dried over sodium sulfate, filtered and concentrated under reduced pressure toyield 8.5 g (96 %) of compound 45A in the form of a white solid., 103-76-4

The synthetic route of 103-76-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (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.278788-66-2,(R)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step B: tert-butyl (3R)-4-[2-(3-cyano-2-methylphenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate: To a solution of 3-( chloroacetyl)-2-methylbenzonitrile (1.7 g, 8.8 mmol) in THF (17.6 mL) was added (R)-4-N-boc-2-hydroxymethyl-piperazine (2.279 g, 10.54 mmol) and DIPEA (3.07 mL, 17.56 mmol) at rt. Thereaction mixture was stirred at rt over the weekend. After concentration, the residue was partitioned between EtOAc and aqueous NaHC03 (saturated). The aqueous layer was extractedwith EtOAc (2x). The combined organic phase was washed with brine, dried over anhydrousMgS04, and filtered. Concentration was followed by purification by prep TLC (silica gel; 10%MeOH/DCM) to give the title compound: LC/MS (M+1t = 374.14, 278788-66-2

As the paragraph descriping shows that 278788-66-2 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics