Analyzing the synthesis route of tert-Butyl 2-methylpiperazine-1-carboxylate

120737-78-2, The synthetic route of 120737-78-2 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.120737-78-2,tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

To a stirred solution of 3-bromobiphenyl (0.70 g, 3.00 mmol) in toluene (10 mL) was added t-butyl 2-methylpiperazine-l-carboxylate (0.720 g, 3.60 mmol), potassium t- butoxide (0.504 g, 4.50 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.090 g, 98.3 mmol) and tri-t-butylphosphine (0.018 g, 89.0 mmol). The mixture was heated at 90 C for 5 hours. At this time the reaction was cooled, diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The residue was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford t-butyl 4-([l, -biphenyl]-3-j/j-2-methylpiperazine- 1-carboxylate (0.750 g, 71%) as a brown oil. The t-butoxycarbonyl protecting group was removed from this compound using General Procedure G to afford l-([l,l’-biphenyl]-3- yl)-3-methylpiperazine. This intermediate was, in turn, was reacted with Intermediate 5 using General Procedure A to generate the title compound. 1H NMR (500 MHz, CDCI3) delta 7.60-7.34 (m, 6H), 7.12-7.11 (m, 2H), 6.92-6.90 (m, 1H), 4.40-4.39 (d, J= 6.5 Hz, 1H), 4.19-4.14 (m, 1H), 3.87-3.33 (m, 4H), 3.09-2.88 (m, 8H), 2.46-2.43 (m, 1H), 1.99-1.55 (m, 9H), 1.38 (t, J = 7.0 Hz, 3H) ppm. 13C NMR (125 MHz, CDC13) delta 156.7, 156.7, 151.9, 142.5, 141.6, 129.5, 128.7, 127.3, 127.2, 119.1, 115.4, 115.4, 115.3, 115.3, 59.0, 54.3, 54.3, 53.2, 53.3, 49.1, 49.1, 47.9, 47.8, 47.7, 47.7, 46.1, 46.0, 39.8, 39.5, 39.1, 39.0, 36.7, 36.4, 25.9, 25.8, 25.4, 24.3, 24.3, 24.1, 24.0, 15.8, 15.7 ppm. Purity: >99% (214 & 254 nm) LCMS; retention time: 1.29 min; (M+H+) 433.3

120737-78-2, The synthetic route of 120737-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
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;,
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Downstream synthetic route of 120737-78-2

As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

120737-78-2, tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2 1-(2,4-Difluorophenyl)-1,4-dihydro-4-oxo-6-fluoro-7-(3-methyl-4-tert-butyloxycarbonyl-piperazin-1-yl)-3-quinoline carboxylic acid A 50 gallon glass lined reactor was purged with nitrogen and charged with 44.5 kg of dimethylsulfoxide, 2.3 kg of triethylamine, 6 kg of methanol, 5.0 kg of 1-(2,4-difluorophenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline carboxylic acid (see U.S. Patent No. 4,730,000) and 12 kg of 1-tert-butyloxycarbonyl-2-methylpiperazine. The slurry was stirred and heated to 95 +- 2C. After 2 hours, 3 kg more of 1-tert-butyloxycarbonyl-2-methylpiperazine and 3 liters of methanol were added. After 4 and 27 hours, respectively 5 kg and 3 kg more of 1-tert-butyloxycarbonyl-2-methylpiperazine were added. After 36 hours, the reaction temperature was lowered to 60C. To the stirred mixture was added 41 liters of isopropanol that had been preheated to 55C. The slurry resulting from the above reaction was cooled to room temperature, filtered and washed with isopropanol. The filter cake was added to 25 liters of 100C acetic acid and heated to reflux. The slurry was cooled to 19C, filtered and washed with isopropanol. The solid was dried at 40C overnight, yielding 3.1 kg of the title compound. m.p. 254-256C. 300 MHz 1H NMR 8.60 (s, 1H), 8.10 (d, 1H), 7.50 (m, 1H), 7.28-7.15 (m, 3H), 6.21 (d, 1H), 4.33 (br d, 1H), 3.94 (br d, 1H), 3.41-3.18 (m, 4H), 2.91 (m, 1H), 2.72 (m, 1H), 1.46 (s, 9H), 1.30 (d, 3H)., 120737-78-2

As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

Reference:
Patent; ABBOTT LABORATORIES; EP350950; (1990); A1;,
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New learning discoveries about 120737-78-2

120737-78-2, As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.120737-78-2,tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

mixture of tert-butyl 2-methylpiperazine- I -carboxylate (0.077 mL, 0.383 mmol), rac-(6S,7R,8R)-5-acetyl-6-cyclopropyl-7-methyl-8-(phenylamino)-5,6,7,8-tetrahyd ro- I ,5-naphthyridin-2-yltrifluoromethanesulfonate (for a preparation see Intermediate 102, 90 mg, 0.192 mmol) and cesium carbonate (187 mg, 0.575 mmol) in 1,4-dioxane (7 mL) had nitrogen bubbled through it for 10 mm. BINAP (23.87 mg, 0.038 mmol) and Pd2(dba)3 (17.55 mg, 0.019 mmol) were added and the reaction mixture was stirred at 90 C under nitrogen for 3 h. The reaction mixture was allowed to cool to rtthen filtered through celite, rinsed with ethyl acetate and concentrated under a stream of nitrogen. The sample was dissolved in 1:1 MeOH:DMSO (2×1 mL) and purified by MDAP (HpH). The appropriate fractions were combined and concentrated in vacuo. The sample was dissolved in DMSO:MeOH (1:1, 1 mL) and purified by MDAP (Formic). The appropriate fractions were combined and concentrated in vacuo to give the product (11 mg, 0.021 mmol, 11.04%) as a yellow gum. Thiswas a racemic mixture of diastereoisomers. LCMS (2 mm Formic): Rt = 1 .40 mi [MH] = 520.

120737-78-2, As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
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Simple exploration of tert-Butyl 2-methylpiperazine-1-carboxylate

120737-78-2 tert-Butyl 2-methylpiperazine-1-carboxylate 15087784, apiperazines compound, is more and more widely used in various fields.

120737-78-2, tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

120737-78-2, Under an argon atmosphere,tert-butyl 2-methylpiperazine-1-carboxylate(1.28 g, 6.40 mmol), 1-bromo-3-fluoro-4-iodobenzene (2.31 g, 7.68 mmol), copper iodide (122 mg, 0.640 mmol)Triopotassium phosphate (4.08 g, 25.6 mmol),Ethylene glycol (716 muL, 12.8 mmol) inA solution of 1-butanol (6 mL) was stirred at 100 C. for 16 h.Water was added to the reaction solution, and the mixture was extracted with ethyl acetate.The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (767 mg, 32%).Clear oil

120737-78-2 tert-Butyl 2-methylpiperazine-1-carboxylate 15087784, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Yakult Honsha Corporation; Abe, Atsuhiro; Mae, Satoyuki; Yamazaki, Ryuta; Sawaguchi, Yuichi; Sugimoto, Takuya; Sasai, Toshio; Nishiyama, Hiroyuki; Nagaoka, Masato; Matsuzaki, Ken; Kurita, Akinobu; Matsui, Makoto; Shingeyama, Takahide; (208 pag.)JP6378918; (2018); B2;,
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Piperazines – an overview | ScienceDirect Topics

Some tips on tert-Butyl 2-methylpiperazine-1-carboxylate

120737-78-2 tert-Butyl 2-methylpiperazine-1-carboxylate 15087784, apiperazines compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.120737-78-2,tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

A solution of tert-butyl 2-methylpiperazine-1-carboxylate (1.5 g, 7.49 mmol, 1 equiv), 2-chloro-5-(trifluoromethyl)pyrimidine (1.37 g, 7.50 mmol, 1.00 equiv), and K2CO3 (2.07 g, 15.0 mmol, 2.00 equiv) in NMP (20 mL) was stirred for 16 h at 85 C. The reaction mixture was cooled to RT, followed by addition of water. The resulting solids were precipitated and collected by filtration, and then washed with water and drying under vacuum to afford 2.5 g of title compound as a light yellow solid. LCMS. [M+H]+ 347., 120737-78-2

120737-78-2 tert-Butyl 2-methylpiperazine-1-carboxylate 15087784, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
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Piperazines – an overview | ScienceDirect Topics

Brief introduction of 120737-78-2

The synthetic route of 120737-78-2 has been constantly updated, and we look forward to future research findings.

120737-78-2, tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

51.1: 2-Methyl-4-(1-m-tolyl-1H-[1,2,4]triazole-3-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester 2.00 g (9.84 mmol) 1-m-tolyl-1H-[1,2,4]-triazole-3-carboxylic acid was stirred with 3.30 g (10.3 mmol) TBTU and 2.50 mL (14.6 mmol) DIPEA in 30 mL DCM at RT. After 10 min, 2.05 g (9.84 mmol) 2-methyl-piperazine-1-carboxylic acid tert-butyl ester was added and the reaction mixture was stirred at RT for 12 h. The solvent was removed by distillation. The residue was taken up in water and extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (EtOAc). Yield: 4.00 g (95%), purity: 90% ESI-MS: m/z=386 (M+H)+ Rt(HPLC): 1.48 min (method 8), 120737-78-2

The synthetic route of 120737-78-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; US2013/158042; (2013); A1;,
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Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of tert-Butyl 2-methylpiperazine-1-carboxylate

As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

120737-78-2, tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of tert-butyl piperazine-1-carboxylate (1 g, 5.37 mmol, 1.00 equiv), 6-chloropyridine-3-carbonitrile (690 mg, 4.98 mmol, 1.00 equiv), potassium carbonate (1.4 g, 10.13 mmol, 2.00 equiv), NMP (20 mL) was stirred for 1 h at 80 C. The resulting solution was quenched by 100 ml of water and extracted with 2¡Á100 mL of EtOAc and the organic layers combined and concentrated under vacuum to afforded 1.2 g (78%) of the title compound as yellow oil. LCMS (ESI, m/z): 303.15 [M+H]+, 120737-78-2

As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

Reference£º
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Analyzing the synthesis route of 120737-78-2

120737-78-2, The synthetic route of 120737-78-2 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.120737-78-2,tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

Step A: To a solution of tert-butyl 2-methylpiperazine-1-carboxylate (340 mg, 1.70 mmol) in THF (5 mL) was added sodium hydride (60%, 82 mg, 2.04 mmol). The reaction mixture was stirred at room temperature for 5 min, then methyl 2-chlorobenzoxazole-4-carboxylate (300 mg, 1.41 mmol) in THF (5 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 19 h. The mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (silica gel, 20% EtOAc in hexane) to afford methyl 2-(4-(tert-butoxycarbonyl)-3-methylpiperazin-1-yl)benzoxazole-4-carboxylate (336 mg, 63%) as yellow solid. MS consistent.

120737-78-2, The synthetic route of 120737-78-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMR TECHNOLOGY, INC.; US2008/255114; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Downstream synthetic route of tert-Butyl 2-methylpiperazine-1-carboxylate

120737-78-2, As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

120737-78-2, tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General Procedure: To a 50 mL screw-cap round bottom flask equipped with a stir bar were added 1 -bromo-2,4-dichlorobenzene (2.0 g, 8.85 mmol), 2-methyl-piperazine-l -carboxylic acid tert-butyl ester (2.13 g, 10.6 mmol), palladium acetate (0.199 g, 0.89 mmol), 2-di-tert- butylphosphenylbiphenyl (0.264 g, 0.48mmol), sodium tert-butoxide (1.02 g, 10.6 mmol) and toluene (20 mL). The reaction flask was sealed and the reaction mixture was heated at 1 10 C overnight. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water (2 x 50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified on silica gel using hexanes.diethyl ether = 95:5 to 90:10 in a gradient fashion, to give the desired product as yellow oil (858 mg, 28 %). 1H NMR (300 MHz, CDCl3): delta 7.28 (d, IH), 7.11 (dd, IH)5 6.85 (d, IH)5 4.28 (bs, IH), 3.89 (d, IH), 3.22 (m, IH), 3.08 (m, 2H), 2.67 (m, 2H), 1.43 (s, 9H), 1.34 (d, 3H).

120737-78-2, As the paragraph descriping shows that 120737-78-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2007/87135; (2007); A2;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

Simple exploration of tert-Butyl 2-methylpiperazine-1-carboxylate

120737-78-2 tert-Butyl 2-methylpiperazine-1-carboxylate 15087784, apiperazines compound, is more and more widely used in various fields.

120737-78-2, tert-Butyl 2-methylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 7-(3,4-dimethoxyphenyl)-5-methyl-4-oxo-4,5-dihydrothieno[3,2-c]pyridine-2- carbaldehyde (for a preparation see Intermediate 25, 100 mg, 0.304 mmol) in DCM (5 mL) was added acetic acid (0.026 mL, 0.455 mmol) and ierf-butyl 2-methylpiperazine-1 -carboxylate (0.073 mL, 0.364 mmol) and the reaction mixture was stirred under nitrogen at room temperature for one hour. Sodium triacetoxyborohydride (322 mg, 1.518 mmol) was then added and the reaction was refluxed under nitrogen overnight. The reaction mixture was allowed to cool to room temperature and was then hydrolyzed with a saturated aqueous solution of sodium bicarbonate (20 mL). The layers were separated and the aqueous phase was extracted with DCM (3 x 10 mL). The combined organic layers were washed with a saturated aqueous solution of sodium chloride solution (approx. 20 mL), dried over magnesium sulphate, filtered and concentrated under vacuum to give a light brown residue. The residue was purified by chromatography on silica gel eluting with 0 to 5% MeOH in DCM. The appropriate fractions were combined to give an impure light brown residue. The product was therefore loaded onto a 2g SCX column and was flushed with MeOH (3 column volumes). The product was eluted in 2.0M ammonia in MeOH (3 column volumes) and concentrated to give ferf-butyl 4-((7-(3,4-dimethoxyphenyl)-5-methyl-4-oxo-4,5-dihydrothieno[3,2-c]pyridin-2- yl)methyl)-2-methylpiperazine-1-carboxylate (1 10 mg, 71 % yield) as a yellow oil. LCMS (2 min, Formic Acid): Rt = 0.90 min, MH+ = 514, 120737-78-2

120737-78-2 tert-Butyl 2-methylpiperazine-1-carboxylate 15087784, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; BAMBOROUGH, Paul; BIT, Rino, Antonio; BROWN, John, Alexander; CAMPBELL, Matthew; LINDON, Matthew, John; SHIPLEY, Tracy, Jane; THEODOULOU, Natalie, Hope; WELLAWAY, Christopher, Roland; WESTAWAY, Susan, Marie; WO2014/78257; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics