Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.438631-77-7,(R)-1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate,as a common compound, the synthetic route is as follows.

To degassed mixture of 68 1,4-dioxane (74.3 ml) and 56 DIPEA (5.86 ml, 33.66 mmol) at rt was added 528 7-bromo-4-chloro-6,8-dimethyl-3-nitroquinoline (3.54 g, 11.22 mmol) followed by 272 1-tert-butyl 3-methyl (3R)-piperazine-1,3-dicarboxylate (4.11 g, 16.83 mmol). The reaction was heated at 100 C. for 48 h. The reaction was then cooled to rt and the solvent was removed in vacuo. The residue was diluted with EtOAc (300 ml) and washed with water (2×250 ml) and brine (100 ml). The organic layer was dried (phase separator) and concentrated in vacuo. The crude product was purified by flash silica chromatography (0 to 50% 57 EtOAc in 58 heptane) to give 530 1-tert-butyl 3-methyl (3R)-4-(7-bromo-6,8-dimethyl-3-nitroquinolin-4-yl)piperazine-1,3-dicarboxylate (4.79 g, 82%) as an orange oil; 1H NMR (400 MHz, DMSO, 30 C.) 1.45 (9H, s), 2.64 (3H, s), 2.88 (3H, s), 3.13-3.21 (1H, m), 3.51 (3H, s), 3.51-3.62 (2H, m), 3.8-3.89 (2H, m), 4.03 (1H, s), 4.31 (1H, s), 8.13 (1H, s), 9.06 (1H, s); m/z: ES+ [M+H]+ 524.9.

438631-77-7, As the paragraph descriping shows that 438631-77-7 is playing an increasingly important role.

Reference：
Patent; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

848482-93-9, (S)-4-(tert-Butoxycarbonyl)piperazine-2-carboxylic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

848482-93-9, To a stirred mixture of (5)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1.0 g, 4.34 mmol) and a2C03 (0.90 g, 10.80 mmol) in water (10 mL) was added solution of FMOC-C1 (1.23 g, 4.77 mmol) in 1,4-dioxane (10 mL) dropwise at 0 °C. The reaction mixture was stirred at room temperature for 16 h then diluted with water (50 mL) and washed with MTBE (25 mL). The aqueous layer was acidified with IN aqueous HQ (10 mL) to pH 2 and extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous a2S04, filtered and concentrated to afford the title compound (0.87 g) as an off- white solid. The crude product was used in the next step without purification.

The synthetic route of 848482-93-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP & DOHME CORP.; BLIZZARD, Timothy Allen; BIFTU, Tesfaye; WO2013/148478; (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.216144-45-5,4-(4-Methylpiperazin-1-yl)benzylamine,as a common compound, the synthetic route is as follows.

Example 103 6-chloro-N-[4-(dimethylphosphoryl)phenyl]-N?-[4-(4-methylpiperazin-1-yl)benzyl]-1,3,5-triazine-2,4-diamine (0712) (0713) To a solution of 4,6-dichloro-N-[4-(dimethylphosphoryl)phenyl]-1,3,5-triazin-2-amine (prepared as in Example 102: 0.12 mmol) in 2 mL of ethanol is added 50 muL of triethylamine and 4-(4-methylpiperazine)-benzylamine (24 mg, 0.12 mmol). The mixture is microwaved at 120 degrees until formation of the desired compound. The reaction mixture is filtered through a syringe filter and purified by prep-HPLC., 216144-45-5

The synthetic route of 216144-45-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (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.960283-58-3,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.

Description 79; 1 ,1 -Dimethylethyl (2S)-4-{[4-(acetylamino)-2-methylphenyl]methyl}-2-methyl-1 – piperazinecarboxylate (D79); lambda/-(4-Formyl-3-methylphenyl)acetamide (D78) (326 mg, 1.8 mmol), 1 ,1 -dimethylethyl (2S)-2-methyl-1 -piperazinecarboxylate hydrochloride (436 mg, 1.8 mmol), triethylamine (0.282 mL, 2 mmol) and sodium tri(acetoxy)borohydride (781 mg, 3.7 mmol) were stirred together in DCE (15 mL) for 17 h. Saturated aqueous NaHCO3 (15 mL) was added and the reaction mixture stirred for 1 h. The organic layer was separated and washed with water and brine, then dried and concentrated to give the crude product which was purified by chromatography. Elution with 0-100% ethyl acetate/petroleum ether yielded the title compound as a colourless oil (573 mg). deltaH (CDCI3, 400MHz) 7.27 (2H, m), 7.16 (1 H, d), 7.11 (1 H, br.s), 4.17 (1 H, m), 3.78 (1 H, m), 3.36 (2H, s), 3.02 (1H, m), 2.70 (1H, m), 2.56 (1 H, m), 2.36 (3H, s), 2.17 (4H, m), 1.95 (1 H, m), 1.45 (9H, s), 1.18 (3H, d). MS (ES): MH+ 362.3., 960283-58-3

As the paragraph descriping shows that 960283-58-3 is playing an increasingly important role.

Reference：
Patent; GLAXO GROUP LIMITED; WO2008/729; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

21091-98-5, (4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone (31.5 g, 126 mmol) was dissolved in methanol (150 ml) and transferred into a 500-ml PARR flask. The PARR flask was flushed with nitrogen, then 500 mg Pd/C (10% Pd) were added. The flask was flushed with nitrogen, then hydrogen, then shaken under a pressure of 50 psi of hydrogen for 17 hours. The mixture was filtered through CELITE, the solid washed with MeOH and concentrated to give 27.2 g beige solid ((4-aminophenyl)(4- methylpiperazin-1-yl)methanone. MS (ESI) m/z 220 (M+H). 1H NMR (CDCl3) delta ppm 7.25 (d, 2 H, J= 7.6), 6.64 (d, 2 H, J= 7.6), 3.86 (bs, 2 H), 3.63 (bs, 4 H), 2.40 (bs, 4H), 2.30 (s, 3H)., 21091-98-5

21091-98-5 (4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone 716396, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok, Vinayak; BATT, Douglas, G.; LIU, Qingjie; JOHNSON, Walter, L.; MASTALERZ, Harold; ZHANG, Guifen; ZIMMERMANN, Kurt; WO2010/80474; (2010); 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.208167-83-3,tert-Butyl 4-(2-chloroethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.,208167-83-3

Step 8: Preparation of tert-butyl 4-[2-[4-(6-benzyloxy-2-phenyl-3,4-dihydro-1H-isoquinolin-1-yl)phenoxy]ethyl]piperazine-1-carboxylate To a solution of 4-(6-benzyloxy-2-phenyl-3,4-dihydro-1H-isoquinolin-1-yl)phenol (2.30 g, 5.64 mmol, 1.00 eq), tert-butyl 4-(2-chloroethyl)piperazine-1-carboxylate (1.68 g, 6.77 mmol, 1.20 eq) in N,N-dimethylformamide (20 mL) was added cesium carbonate (2.76 g, 8.46 mmol, 1.50 eq) and potassium iodide (94 mg, 0.56 mmol, 0.10 eq) under nitrogen atmosphere. The reaction mixture was stirred at 90 C. for 16 hours. LC/MS showed most of the starting material was consumed. Water (150 mL) was added to the mixture, the resulting mixture was extracted with ethyl acetate (50 mL*3). The combined organic phase was washed with brine (100 mL*2), dried over sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=20/1 to 1/1) to give tert-butyl 4-[2-[4-(6-benzyloxy-2-phenyl-3,4-dihydro-1H-isoquinolin-1-yl) phenoxy]ethyl]piperazine-1-carboxylate (2.5 g, 3.97 mmol, 70% yield, 98% purity) as a yellow solid. LC/MS (ESI) m/z: 620.3 [M+1]+; 1H-NMR (400 MHz, DMSO-d6) delta 7.44-7.37 (m, 4H), 7.32-7.28 (m, 2H), 7.17-7.11 (m, 4H), 6.87-6.80 (m, 6H), 6.64 (t, J=7.2 Hz, 1H), 5.84 (s, 1H), 5.07 (s, 2H), 4.06-3.98 (m, 2H), 3.67-3.62 (m, 1H), 3.44-3.40 (m, 1H), 3.29-3.27 (m, 4H), 2.96-2.79 (m, 2H), 2.65 (t, J=5.6 Hz, 2H), 2.39 (t, J=4.8 Hz, 4H), 1.38 (s, 9H).

208167-83-3 tert-Butyl 4-(2-chloroethyl)piperazine-1-carboxylate 22106269, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; Arvinas, Inc.; Crew, Andrew P.; Qian, Yimin; Dong, Hanqing; Wang, Jing; Hornberger, Keith R.; Crews, Craig M.; (864 pag.)US2018/155322; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

115619-01-7, 4-(4-Ethylpiperazin-1-yl)phenylamine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5 (0.10g, 0.48mmol), DIPEA (0.08ml, 0.48mmol) and EtOH (5ml) was mixed with the 85 (0.07g, 0.48mmol) and refluxed for 2.5hrs. The reaction was quenched by saturated NaHCO3 (aq.) and the mixture was extracted by ethyl acetate (30ml x 3). The residue was purified by flash column over silica gel (dichloromethane: methanol = 9: 1, Rf = 0.28) to afford 89 (0.05g, 33.24%) as a pale yellow solid. 1H-NMR (300MHz, CDCl3): delta 1.13 (t, J= 7.2 Hz, 3H), 2.46 (q, J= 7.2 Hz, 2H), 2.62 (t, J= 5.1 Hz, 4H), 2.98 (d, J= 5.1 Hz, 3H), 3.19 (t, J= 5.1 Hz, 4H), 5.17-5.29 (m, 1H), 5.55 (br, 1H), 6.91 (d, J= 8.7 Hz, 2H), 7.37 (d, J= 8.1 Hz, 1H), 7.46 (s, 1H), 8.20 (d, J= 44.7 Hz, 1H)., 115619-01-7

The synthetic route of 115619-01-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; TAIPEI MEDICAL UNIVERSITY; YEN, Yun; LIOU, Jing-Ping; CHEN, Chun-Han; (70 pag.)WO2017/15400; (2017); 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.314741-40-7,(S)-tert-Butyl 3-(hydroxymethyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

A solution of iert-butyldimethylsilyl chloride (1.53 g, 10.17 mmol) in DCM (10 ml) was added dropwise to (5)-4-A/-Boc-2-hydroxymethyl-piperazine (2 g, 9.25 mmol) and triethylamine (2.58 ml, 18.49 mmol) in DCM (50 ml) at 20C over a period of 5 minutes under air. The resulting solution was stirred at 20C for 16 hours then evaporated to dryness. The residue was purified by flash silica chromatography, elution gradient 0 to 5% EtOH in EtOAc. Pure fractions were evaporated to dryness to afford te/t-butyl (S)-3-(((ieri-butyldimethylsilyl)oxy)methyl)piperazine-l-carboxylate (2.84 g, 93%) as a colourless oil. 1H NM (500 MHz, CDCI3) 0.00 (s, 6H), 0.84 (s, 9H), 1.40 (s, 9H), 2.48 (s, 1H), 2.6 – 2.87 (m, 3H), 2.92 (d, J = 11.5 Hz, 1H), 3.41 (dd, J = 7.2, 9.8 Hz, 1H), 3.52 (s, 1H), 3.85 (s, 2H).

314741-40-7, The synthetic route of 314741-40-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTRAZENECA AB; KETTLE, Jason, Grant; BAGAL, Sharanjeet, Kaur; BOYD, Scott; EATHERTON, Andrew, John; FILLERY, Shaun, Michael; ROBB, Graeme, Richard; RAUBO, Piotr, Antoni; (144 pag.)WO2018/206539; (2018); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

78551-60-7, tert-Butyl 4-benzyl-3-oxopiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,78551-60-7

To a solution of oxalyl chloride (1.08 g, 8.30 mmol) in CH2CI2 (7 ml) in a dryice-acetone bath was added DMSO (1.14 g, 14.6 mmol). After 5 min, a solution ofthe product of Step 3 (3.01 g, 7.34 mmol) in CH2CI2 (7 ml) was added and the mixturewas stirred for 1 h. Diisopropylethylamine (3.28 g, 25.4 mmol) was added and after 2min the cooling bath was removed. The mixture was stirred for 30 min and dilutedwith water (50 ml). CH2CI2 (40 ml) was added and the aqueous layer was extractedwith CH2CI2 (40 ml). The combined organic layer was washed with brine, dried(MgSC>4), and concentrated to give the aldehyde, which was not further purified.To a solution of diisopropylamine (896 mg, 8.85 mmol) in THF (5 ml) in a dryice-acetone bath was added 1.6 M butyllithium in hexanes (5.5 ml, 8.8 mmol). After 5min the mixture was put in an ice-water bath and stirred for 20 min. The solution wascooled in the dry ice-acetone bath again and a solution of the product of Step 5 (2.14g, 7.37 mmol) in THF (8 ml) was added. The mixture was stirred for 1 h. A solutionof the above aldehyde in THF (10 ml) was added and the mixture was stirred for 1.5h. The reaction was quenched with water and partitioned between ether (4×50 ml)and water (50 ml). The combined organic layer was washed with brine (50 ml), dried(MgSO4), concentrated, and purified by column chromatography (gradientEtOAc/Hexanes 0-20%) to give the product (2.67 g, 52%). MS m/e 698 (M+H)+

The synthetic route of 78551-60-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SCHERING CORPORATION; WO2006/14762; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

262368-30-9, N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound (Z) -1- acetyl-3- (methoxy (-2H- tetrahydro-thiopyran-4-yl) methylene) -2-oxo-indole-6-carboxylate Lin ( 600mg, 1.6mmol), 4- (N- methyl-2- (4-methyl-piperazin-1-yl) acetamide) aniline (251mg, 0.96mmol) and potassium hydroxide (50mg, 0.8mmol) was dissolved in 50mL of methanol, the reaction was stirred overnight at 50 deg.] C, the solvent was spin, 50mL of water was added, the mixture with dichloromethane (20mL × 3). the organic phase was dried over anhydrous sodium sulfate, the solvent was spin, the crude product was purified by silica gel column (dichloromethane: methanol = 50: 1) isolated as a dark red solid.(26mg, 3%)

262368-30-9, The synthetic route of 262368-30-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Shandong Hengli medical science and Technology Co Ltd; Luo, haoxian; Wang, aichen; (42 pag.)CN103848814; (2016); B;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics