Heterocyclic Building Blocks-piperazine

74879-18-8, (S)-(+)-2-Methylpiperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

C. Preparation of (S)-5-bromo-4-(3-methylpiperazin-1-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. To a mixture of pyrrolopyrimidine from step B (76 mg, 0.2 mmol) and (S)-2-methylpiperazine (21 mg, 0.2 mmol) in isopropanol (2 ml) was added triethylamine (0.11 ml, 0.8 mmol). The mixture was heated at 80 C. for 5 mins via microwave and concentrated under vacuum to give crude (S)-5-bromo-4-(3-methylpiperazin-1-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (65 mg, 0.15 mmol, 75%) which was used directly for the next step. MS (ES+) [M+H]+=437., 74879-18-8

74879-18-8 (S)-(+)-2-Methylpiperazine 2734219, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Harrison, Bryce Alden; Kimball, Spencer David; Mabon, Ross; Rawlins, David Brent; Rice, Dennis S.; Voronkov, Michael Victor; Zhang, Yulian; US2009/42893; (2009); A1;,
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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, To (S)-2-methyl piperazine (0.150 g, 1.5 mmol) was added 4-bromobenzotrifluoride (0.225g, 1.0 mmol), dichloro-bis(tri-o-tolyphosphine) palladium (II) (0.236 g, 0.3mmol), and sodium t-butoxide (0.144 g, 1.5 mmol), and toluene (2 mL) sequentially. After nitrogen was bubbled through the mixture for 15 minutes, the reaction was heated to lOO’C. The reaction was stirred at 1000C for 2 hr. The reaction was filtered through celite and concentrated under reduced pressure. The residue was then purified on a 1000 micron preparative thin layer chromatography plate eluting with 5% MeOH in dichloromethane to yield the title compound as an oil. IH NMR (500 MHz, CDCl3) delta 7.5 (d, 2H, J=8.7Hz), 6.95 (d, 2H, J = 8.7 Hz), 3.71 (d, 2H, J=IOHz), 3.20 (m, IH), 3.04 (m, 2H), 2.85 (m, 1H),2.48 (m, IH), 1.24 (d, 3H, J=7.2Hz). LC/MS 247 (M+l); HPLC 2.41 min

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

Reference£º
Patent; MERCK & CO., INC.; WO2007/70173; (2007); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5464-12-0,1-(2-Hydroxyethyl)-4-methylpiperazine,as a common compound, the synthetic route is as follows.

5464-12-0, A one dram vial was charged with solid potassium tert-butoxide (54 mg, 0.48 mmol), 2-(4-methylpiperazin-l-yl)ethanol (0.075 g, 0.52 mmol), and tert-butanol (0.3 mL, 3.4 mmol). The mixture was stirred at ambient temperature for 30 minutes. N-(3-cyclopropyl-l-((l-methyl-2-oxo-l,2-dihydropyridin-3- yl)methyl)-lH-indazol-4-yl)-7-fluoroimidazo[l,2-a]pyridine-3-carboxamide (0.032 g, 0.070 mmol) was added in one portion. The mixture was heated at 88 ¡ãC with stirring for 16 hours. The mixture was cooled to ambient temperature and diluted with water until a precipitate formed. The precipitate was isolated by filtration and dried under high vacuum. Purification using silica preparative thin layer chromatography plate (20 x 20 cm, 0.5 mm) developed in a chamber with 10percent methanol/dichloromethane with 0.6percent concentrated ammonium hydroxide gave the product. MS (APCI), positive scan, m/z = 581.2 (M+).

As the paragraph descriping shows that 5464-12-0 is playing an increasingly important role.

Reference£º
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BRADLEY, Michael; DELISLE, Robert Kirk; HENNINGS, D. David; KENNEDY, April L.; MARMSATER, Fredrik P.; MEDINA, Matthew; MUNSON, Mark C.; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2011/79076; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50606-32-1,Butyl piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

50606-32-1, 3.2. 4-((S)-2-tert-Butoxycarbonylamino-4-ethoxycarbonyl-butyryl)-piperazine-l-carboxylic acid butyl ester To a solution of intermediate 3.1 (8.75 g) in CH2Cl2 (50 mL) / THF (20 mL) was added HOBT (4.94 g). After 15 min, was added EDCI-HCl (6.70 g) and the reaction mixture further stirred for 20 min. Piperazine-1-carboxylic acid butyl ester (6.22 g, prepared as described in WO2008044217) was added and the reaction mixture stirred until reaction completion at RT. The mixture was poured onto an ice-cold aq. citric acid solution (5%), and the precipitate filtered off. The filtrate was extracted with Et2O (3×200 mL), the org. phase washed with aq. citric acid (5%, 4×50 niL), sat. aq. Na2CO3 solution and brine. The combined org. layers were dried over MgSO4 and evaporated to give 13.O g of the desired product. LC-MS: tR = 1.01 min; [M+H]+: 444.49.

50606-32-1 Butyl piperazine-1-carboxylate 21963126, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; HILPERT, Kurt; HUBLER, Francis; LEHMANN, David; MEYER, Emmanuel; RENNEBERG, Dorte; WO2010/122504; (2010); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5521-39-1,2-(4-(4-Aminophenyl)piperazin-1-yl)ethanol,as a common compound, the synthetic route is as follows.,5521-39-1

Synthesis of //ONo.is-4-(5-Bromo-2-{4-[4-(2- hydroxy-ethyl)-piperazin-l-yl]-phenylamino}-pyrimidin-4-ylamino)adamantan-l-ol:Conc.HCl (20mL) was added to a mixture of tra?s-4-(5-bromo-2-chloropyrirnidin-4- ylamino)adamantan-l-ol (50mg, 139 mmoles) and 2-[4-(4-aminophenyl)piperazin-l- yl]ethanol (37mg, 0.167mmoles) in n-butanol (3ml) was and the mixture was heated at 1 10- 120 overnight. The reaction mixture was cooled to 80, n-butanol (5 ml) was added and filtered. The residue was triturated with hot MeOH, purified by preparative HPLC to afford lOmg of trara-4-(5-Bromo-2-{4-[4-(2-hydroxy-ethyl)-piperazin-l-yl]-phenylamino}- pyrimidin-4-ylamino)adamantan-l-ol inl3% yield.’H NMR (DMSO-d6) delta 10.2-10.35 (br s, H), 9.2-9.3 (br s,lH), 8.1-8.2 (s,lH), 7.5 (d,2H), 7.0 (d,2H)?6.2(s,lH), 3.0-4.0 (m,12H), 2.2-2.3 (s,2H), 2.0-2.1 (s,lH), 1.6-1.8 (m,7H), 1.3-1.5 (m,4H) LC-MS: 543 (M + l)

The synthetic route of 5521-39-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SENGUPTA, Saumitra; RAJAGOPALAN, Srinivasan; BELAVAGI, Ningaraddi; RAMACHANDRA, Muralidhara; WO2012/59932; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13889-98-0,1-Acetylpiperazine,as a common compound, the synthetic route is as follows.

General procedure: 4-Fluorobenzaldehyde and various piperazine/azole derivatives were reacted by using potassium carbonate as catalyst in DMSO as mentioned in the literature [26]., 13889-98-0

The synthetic route of 13889-98-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Krishna, Vagolu Siva; Sirim, Mustafa Mert; Sriram, Dharmarajan; Unsal Tan, Oya; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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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

Into a 500 mL reaction flask, 200 mL of methanol was added to 25.0 g of methyl (3-chloro-3-phenylmethylene)-2-oxoindoline-6-formate oil which was obtained by rotary evaporation from the previous reaction step, stirred until fully dissolved, 20.9 g of compound VI and 15.5 g of diisopropylethylamine were added, heated to 50-60 C. and reacted for 10 hours until TLC showed the disappearance of the raw materials. The reaction solution was evaporated to dryness and replaced with 200 mL of ethyl acetate, washed with water (100 mL*3 times), and then 6.6 g of anhydrous magnesium sulfate was added for drying and 6.6 g of activated carbon was added for decolorization successively. The obtained solution was evaporated to dryness and replaced with methanol/n-heptane, crystallized to obtain 37.1 g of nintedanib, yield 86.1%. 1H NMR (400 MHz, DMSO-d6): 12.17 (s, 1H), 11.03 (s, 1H), 7.64-7.59 (t, J=7.6 Hz, 2H), 7.56-7.52 (t, J=7.6 Hz, 2H), 7.50-7.45 (d, J=7.6 Hz, 1H), 7.43-7.40 (d, J=1.6 Hz, 1H), 7.21-7.17 (d, J=8.3 Hz, 1H), 7.15-7.07 (m, 2H), 6.82-6.77 (m, 2H), 5.85-5.83 (d, J=8.3 Hz, 1H), 3.79 (s, 3H), 3.11-3.04 (m, 3H), 2.75-2.66 (m, 2H), 2.27-2.19 (m, 5H), 2.16-2.11 (m, 3H), 2.10 (s, 3H). Mass: 540.2 [M+H+]., 262368-30-9

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

Reference£º
Patent; Zhejiang Huahai Pharmaceutical Co., Ltd.; Shanghai Syncores Technologies, Inc.; Li, Zeng; Cheng, Xiaosong; He, Xianliang; Zhang, Jicheng; Huang, Luning; Tao, Anping; Gu, Hong; (14 pag.)US2020/48225; (2020); A1;,
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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

278788-66-2, Into a 5-mL-pressure tube was added 183mg (l.Ommol) of 2,3-difluoro-5- (trifluoromethyl)pyridine, 216mg (l.Ommol) of 1,1-dimethylethyl (3i?)-3-(hydroxymethy I)-I- piperazinecarboxylate, 0.2mL DlEA and 1.OmL DMSO. The mixture was heated at 80 C for overnight. The resulting mixture were filtered and concentrated in vacuo. The residue was purified by using a Gilson preparative HPLC system with a Waters Xterra (C-18) column 100 mm by 50 mm ID, eluting with 20% B to 99% B in 10 min, where A = H2O and B = CH3CN pumped at 150 mL/min to yield 1,1-dimethylethyl (3i?)-4-[3-fluoro-5-(trifluoromethyl)-2-pyridinyl]-3- (hydroxymethyl)- 1 -piperazinecarboxylate as a solid. MS(ESI) 380 [M+H] +.To 20mg (0.053mmol) of 1,1-dimethylethyl (3i?)-4-[3-fluoro-5-(trifluoromethyl)-2- pyridinyl]-3-(hydroxymethyl)-l -piperazinecarboxylate was added 0.5mL DMSO and 20mg of tBuOK in a 5-mL-pressure tube. The mixture was heated at 110 C for overnight. The mixture was filtered and the solution was purified by using a Gilson preparative HPLC system with a Waters Xterra (C- 18) column 100 mm by 50 mm ID, eluting with 20% B to 99% B in 10 min, where A = H2O and B = CH3CN pumped at 150 mL/min to yield 1,1-dimethylethyl (6ai?)-3-(trifluoromethyl)- 6a,7,9,10-tetrahydropyrazino[l,2-rf]pyrido[3,2-][l,4]oxazine-8(6H)-carboxylate as a solid. MS(ESI) 360 [M+H]+.To 40mg of (0.1 lmmol) of 1,1-dimethylethyl (6alphai?)-3-(trifluoromethyl)-6alpha,7,9,10- tetrahydropyrazino[l,2-cr|pyrido[3,2-][l,4]oxazme-8(6H)-carboxylate was added ImL DCM and 0.5mL 50% of TFA in DCE. The mixture was stirred at rt for 6h and concentrated in vacuo (the extra TFA was removed by adding DCE and re-concentrating) to yield crude the TFA salt of (6ocR)- 3-(trifluoromethyl)-6,6alpha,7,8,9,10-hexahydropyrazino[l,2-rf]pyrido[3,2-A][l,4]oxazine. MS(ESI) 260 [M+H]1. The above TFA salt of (6alphai?)-3-(trifluoromethyl)-6,6alpha,7,8,9,10-hexahydropyrazino[l,2- rf]pyrido[3,2-ib][l,4]oxazine were dissolved in 1.OmL DCM and 0.3mL DIEA. Then lOOmg (mmol) of (S)-(+)-Camphotau sulfonylchloride in 0.5mL DCM was slowly added at 0 C. The mixture was stirred at rt for 2h. The resulting solution was concentrated in vacuo. The residue was purified by using a Gilson preparative HPLC system with a Waters Xterra (C- 18) column 100 mm by 50 mm ID, eluting with 20% B to 99% B in 10 min, where A = H2O and B = CH3CN pumped at 150 mL/minto yield (l?,4Z?)-7,7-dimethyl-l-({[(6 alphai?)-3-(trifluoromethyl)-6 alpha,7,9,10- tetrahydropyrazino[ 1 ,2-Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/76318; (2007); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.109-07-9,2-Methylpiperazine,as a common compound, the synthetic route is as follows.

Example 9 In a 100 ml four-neck flask, 5.06 g (= 0.0505 mole) of racemic 2-methylpiperazine was placed, and 50.00 g of 1-butanol (water content 0.05 wt%) was added for dissolution. After cooling down to 0C, 10.91 g (= 0.0500 mole, 0.99 molar time) of di-tert-butyl dicarbonate was added dropwise with the liquid temperature kept in a range from 5 to 15C. Then, stirring was carried out at 5 to 10C for 2 hours. The reaction solution was analyzed, and as a result, the conversion of 2-methylpiperazine was 94.7%, while the selectivity of 1-tert-butoxycarbonyl-3-methylpiperazine was 89.3% (reaction yield 84.6%).Example 10 An experiment was carried out as described for Example 9, except that the amount of di-tert-butyl dicarbonate used was changed to 11.97 g (= 0.0548 mole, 1.10 molar times). As a result, the conversion of 2-methylpiperazine was 100.0%, and the selectivity of 1-tert-butoxycarbonyl-3-methylpiperazine was 81.5% (reaction yield 81.5%)., 109-07-9

109-07-9 2-Methylpiperazine 66057, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; Toray Fine Chemicals Co., Ltd.; EP1548010; (2005); A1;,
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5625-67-2, Piperazin-2-one is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5625-67-2, To a solution of piperazinone (10.0 g, 100 mmol), triethylamine (20.2 g, 200mmol), and DMAP (50 mg) in CH2CI2 (250 ml) in an ice-water bath was added(Boc)2O (22.9 g, 105 mmol) slowly. The mixture was stirred in the ice-water bath for 1h and at RT for 4.5 h. The mixture was diluted with CH2CI2 (250 ml), washed withwater (200 ml), 5% citric acid (200 ml), 1N HCI (200 ml), saturated sodiumbicarbonate (20 ml) and brine. The organic layer was dried (MgSCU) andconcentrated to give the product (18.0 g, 90%). MS m/e 201 (M+H)+

5625-67-2 Piperazin-2-one 231360, apiperazines compound, is more and more widely used in various fields.

Reference£º
Patent; SCHERING CORPORATION; WO2006/14762; (2006); A1;,
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