Tag: M.W:300-400

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1001180-21-7,(R)-tert-Butyl 4-(5-methyl-7-oxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

A flask was equipped with a thermocouple, mechanic stirrer, a nitrogen inlet and drying tube. To the flask was added (R)-tert-buty 4-(5-methyl-7-oxo-6,7-dihydro-5H- cyclopenta[i ]pyrimidin-4-yl)piperazine-l -carboxylate (46.0 g, 139 mmol) followed by dichloromethane (1.10 L) and RuCl(TsDACH) catalyst (1.50 g, 2.80 mmol) with nitrogen degassing (gas dispersion tube) and agitation at room temperature. To the mixture was added triethylamine (23.0 mL, 167 mmol) with degassing. Formic acid (7.40 mL, 195 mmol) was slowly added to the mixture at a rate of about 1 mL/min. Good agitation with stirring was maintained until complete consumption of starting material (about 8-12 hr) as determined by HPLC analysis. The reaction was quenched with saturated sodium bicarbonate (2.00 vol., 100 mL), the layers were separated and the aqueous layer was discarded. The organic layer was washed with saturated sodium bicarbonate, saturated ammonium chloride and brine (2.00 vol., 100 mL each). The organics were dried over sodium sulfate, filtered and solvent exchanged into methanol. The methanolic solution (5.00 vol.) of crude product was charged with 50 wt % SiliaBond Thiol (Silicycle, Inc.) and 20 wt% Charcoal. The mixture was heated to about 50 C and maintained at that temperature with good stirring overnight. The mixture was cooled to room temperature, filtered over a pad of Celite and then polish filtered through a 0.45 micron filter. The mixture was distilled to a minimum working volume and concentrated under reduced pressure to afford the product (44.0 g, 95 % yield), as a 96:4 mixture of trans/cis diastereomers) as solid. Trace amount of Ru metal was measured by ICP-EOS and found that the product contained less than about 20 ppm Ru. The product was purified by preparative HPLC under the following conditionsor crystallization from ethyl acetate/heptane to yield 98.4 % pure product, 97.7 % de with about 100% ee., 1001180-21-7

The synthetic route of 1001180-21-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; LANE, Jonathan W.; REMARCHUK, Travis; SHAKYA, Sagar; SPENCER, Keith L.; STENGEL, Peter J.; WO2013/173736; (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.112257-12-2,tert-Butyl 4-(2-bromoacetyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

4-(2-bromoacetyl)piperazine-1-carboxylate (9.77 mmol, 1 eq.) in methanol (26 ml) at 0C. The reaction vial was sealed and the mixture stirred vigorously overnight at room temperature. The solvent was subsequently evaporated, the residue dissolved in hydrogen chloride (aqueous soln., 0.1 N, 100 ml) and extracted with ethyl acetate (3 x 100 ml). The pH of the recovered aqueous layer was adjusted to 10 by addition of sodium hydroxide (aqueous soln., 1 N), then the organics extracted with ethyl acetate (3 x 100 ml). The combined organic layers were dried over magnesium sulfate, filtered and the solvent evaporated under vacuum to give a light yellow crude product. Further trituration in diethyl ether conducted to the desired amine as a white solid used for the next step without additional purification. C11 H21N3O3; yield 58%; white solid; m.p. 159-160 C; M = 243.30 g/mol; IR (ATR): v = 2974 (w), 1675 (s), 1627 (s), 1417 (m), 1360 (m), 1235 (m), 1172 (m), 1123 (m), 990 (m), 759 (m) cm – ; H NMR (250 MHz, CDCI 3) delta 3.71-3.41 (m, 10H), 1.46 (s, 9H); C NMR (63 MHz, CDCI 3) delta 169.5 (C q), 154.6 (C q), 80.5 (C q), 50.4 (CH 2), 44.6 (2CH 2), 41.7 (2CH 2); HRMS: calcd. for CHH21 3O3 244.1661 , found. 244.1657;, 112257-12-2

The synthetic route of 112257-12-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ASTON UNIVERSITY; GRIFFIN, Martin; RATHBONE, Daniel; BADARAU, Leonas Eduard; WO2014/57266; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

113028-17-4, Ethyl 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,113028-17-4

Example 10: Preparation of prulifloxacin hydrochloride; Method A: To the mixture of dimethylformamide (1.5 It) and 6-fluoro-l-methyl-4-oxo-7-(l- piperazinyl)-lH,4H-[l,3]thiazeto[3,2-a]quinoline-3-carboxylic acid (0.3kg), 4-bromomethyl-5- methyl- 1, 3 -dioxolen-2-one, obtained above was added and cooled to 0-50C. Triethylamine (0.87kg) in dimethylformamide (0.3 It) was added slowly in 1-2 hours. After completion of the reaction (monitored by TLC), dichloromethane (3.0 It) and water (1.5 It) were added to the reaction mixture. The layers were separated and aqueous layer was extracted twice with dichloromethane (1.5 It). All organic layers were combined, dried over sodium sulfate followed by distillation. Methanolic hydrochloride (20-25 % w/w, 0.24 It) was added to organic layer at 0- 5C and stirred. The solid, thus precipitated out was filtered, washed with dichloromethane and dried to obtain 0.36kg of the title compound having purity 92.73 % by HPLC. Example 11: Purification of prulifloxacin hydrochlorideDimethylformamide (1.34 It) was added to prulifloxacin hydrochloride (67g) and reaction mass was heated to 110-112C for 1 hour. The reaction mixture was cooled to 25-300C and stirred for 2 hours, filtered, washed with N,iV-dimethylforamide. The product was slurry washed with isopropanol (0.670 It) and dried to obtain 48.8g of title compound having purity 99.30 % by HPLC.

113028-17-4 Ethyl 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate 10249018, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; IND-SWIFT LABORATORIES LIMITED; WO2009/93268; (2009); 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.112257-12-2,tert-Butyl 4-(2-bromoacetyl)piperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

4-(2-Oxo-2-piperazin-1-ylethyl)morpholine (42-2) Morpholine (0.22 g, 2.59 mmol), 42-1 (0.61 g, 1.99 mmol) and DIEA (0.33 g, 2.59 mmol) were dissolved in DMF (2 mL) and stirred for 18 hours at room temperature. The DMF was then removed under reduced pressure and the residue partitioned between water and methylene chloride. The methylene chloride was drawn off, dried and evaporated to a solid to afford 42-2. This recovered product was treated with neat trifluoroacetic acid and the excess trifluoroacetic acid evaporated off. The resulting residue was partitioned between methylene chloride and aqueous Na2CO3. The free base did not extract from the aqueous so the aqueous was evaporated to dryness, washed the methanol, and the solids filtered off to afford 42-2. 1H-NMR(CD3O): 3.69(t, 4H); 3.59 (t, 2H); 3.54(t, 2H); 3.22(s, 2H); 2.83(t, 2H); 2.77(t, 2H); 2.49(t, 4H).

112257-12-2, 112257-12-2 tert-Butyl 4-(2-bromoacetyl)piperazine-1-carboxylate 15829155, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; Bilodeau, Mark T.; Hartman, George D.; Hoffman JR., Jacob M.; Sisko, John T.; Manley, Peter J.; Smith, Anthony M.; Tucker, Thomas J.; Lumma JR., William C.; Rodman, Leonard; US2002/137755; (2002); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

509073-62-5, tert-Butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of compound 8 (6.0 g, 20 mmol) in H2O (8 mL) andEtOH (24 mL) was added Fe (4.5 g, 80 mmol) and NH4Cl (1.5 g,28 mmol). The mixture was heated under reflux for 2 h. The solidwas filtered off and the liquid was concentrated under vacuum toafford the crude product. The crude product was purified by columnchromatography to provide compound 9 as yellow solid (5.7 g,yield: 93%). Mp: 155-156 C. 1H NMR (400 MHz, CDCl3) delta 7.25 (d,J = 8.4 Hz, 2H), 6.65 (d, J = 8.4 Hz, 2H), 3.94 (s, 2H), 3.59 (s, 4H), 3.44(s, 4H), 1.47 (s, 9H). 13C NMR (100 MHz, CDCl3) delta171.02, 154.54,148.36, 129.26, 124.44, 114.10, 80.15, 44.01, 43.30, 28.29.

509073-62-5, 509073-62-5 tert-Butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate 2764459, apiperazines compound, is more and more widely used in various fields.

Reference：
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

182618-86-6, 1-Boc-4-(4-Nitrophenyl)piperazine is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 17b 4-(4-Amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 4-(4-Amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester was prepared from 4-(4-Nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester, (as prepared in Reference Example 17a) as prepared in Reference Example 13b., 182618-86-6

The synthetic route of 182618-86-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Pierson, Edward; Sohn, Daniel; Haeberlein, Markus; Davenport, Timothy; Chapdelaine, Marc; Horchler, Carey; McCauley, John P.; US2003/13708; (2003); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

288251-87-6, tert-Butyl 4-(2-cyano-4-nitrophenyl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(2-Cyano-4-nitro-phenyl)-piperazine-l -carboxylic acid tert-butyl ester (587 mg, 1.77 mmol) was dissolved in methanol (50 mL) and to this solution was added ammonium chloride (945 mg, 17.66 mmol) and zinc (1155 mg, 17.66 mmol). The mixture was magnetically stirred for 3 hr and the mixture was filtered through a pad of celite. The solids were rinsed with methanol and the combined filtrate was concentrated to a yellow solid. This crude intermediate was dissolved in ethyl acetate (400 mL) and the resulting solution was washed with water (400 mL) and brine (200 mL). The organic layer was collected, dried over sodium sulfate, and concentrated to give 4-(4-amino-2-cyano- phenyl)-piperazine-l-carboxylic acid tert-butyl ester that was used in the next step without further purification., 288251-87-6

The synthetic route of 288251-87-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/141976; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

1001180-21-7, (R)-tert-Butyl 4-(5-methyl-7-oxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 40; 2-(4-chlorophenyl)-l-(‘4-((5R)-7-hydroxy-5,7-diniethyl-6,7-dihvdro-5H-cvclopenta[dlpyrimidin-4- vDpiperazin- 1 -ylV S-fisopropylamino’propan- 1 -one; Step 1 :; A solution of (R)-tert-butyl 4-(5-methyl-7-oxo-6,7-dihydro-5H- cyclopenta[d]pyrimidin-4-yl)piperazine-l-carboxylate (40 nig, 0.120 mmol) in THF (4 niL) was added to a 1.5M solution of methyllithium in diethyl ether (0.088 mL, 0.132 mmol) at -780C. The resulting mixture was stirred at -78C for 1 hour and quenched by saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (2 X). The organic layer was dried (MgSO^ and concentrated. The residue was purified by a silica catridge (5.0 g) eluted by EtOAc to give tert-butyl 4-((5R)-7-hydroxy-5,7-dimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine- 1-carboxylate as an off-white solid (29 mg, 69%). LCMS (APCI+) [M-Boc+H]+ 349.1; Rt: 2.49 min.

1001180-21-7, The synthetic route of 1001180-21-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; MITCHELL, Ian, S.; BLAKE, James, F.; XU, Rui; KALLAN, Nicholas, C.; XIAO, Dengming; SPENCER, Keith, Lee; BENCSIK, Josef, R.; LIANG, Jun; SAFINA, Brian; ZHANG, Birong; CHABOT, Christine; DO, Steven; WO2008/6040; (2008); 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.181955-79-3,1,4-Di-Boc-piperazine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Intermediate 141 : (+/-)-1 ,4-bis(1 ,1-dimethylethyl) 2-methyl 1 ,2,4-piperazinetricarboxylate; In a 500 ml. round-bottomed flask, 22.6 g of intermediate 140 (68.4 mmole) were dissolved in 160 ml. of DCM and 40 ml. of methanol to give a colorless solution. 58 ml. of Trimethylsilyl diazomethane (1 16 mmole) were added dropwise keeping the internal temperature below +2 0C. The solution was allowed to reach RT and was stirred at RT for 2 h. The mixture was carefully evaporated under reduced pressure (Tbath = 35C) and the solid residue was triturated with 100 ml. of pentane, filtered and dried in vacuo to obtain 21 g of desired product as a white solid. The mother liquor was concentrated in vacuo to give 2.5 g of the title compound. UPLC-MS [Acquity UPLC BEH C18, 50×21 mm, 1.7 mum, Mobile phases: A: H2O +0.1% HCOOH/B: MeCN+0.06% HCOOH. Gradient: t=0 min: 97%A, 3% B, t= O.i min 94%A, 6%B t=0.6min 30%A, 70%B t=1.10min 1%A, 99%B t=1.45 min 97%A, 3%B t=1.50min 97%A ,3%B flow rate: 1 ml/min, UV range wavelength 210-350nm]: R1 = 0.80 min, m/z (ES): 344 [M+H]+, 367 [M+Na]+., 181955-79-3

As the paragraph descriping shows that 181955-79-3 is playing an increasingly important role.

Reference：
Patent; GLAXO GROUP LIMITED; WO2008/148853; (2008); 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.181955-79-3,1,4-Di-Boc-piperazine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Intermediate 141 : (+/-)-1 ,4-bis(1 ,1-dimethylethyl) 2-methyl 1 ,2,4-piperazinetricarboxylate; In a 500 ml. round-bottomed flask, 22.6 g of intermediate 140 (68.4 mmole) were dissolved in 160 ml. of DCM and 40 ml. of methanol to give a colorless solution. 58 ml. of Trimethylsilyl diazomethane (1 16 mmole) were added dropwise keeping the internal temperature below +2 0C. The solution was allowed to reach RT and was stirred at RT for 2 h. The mixture was carefully evaporated under reduced pressure (Tbath = 35C) and the solid residue was triturated with 100 ml. of pentane, filtered and dried in vacuo to obtain 21 g of desired product as a white solid. The mother liquor was concentrated in vacuo to give 2.5 g of the title compound. UPLC-MS [Acquity UPLC BEH C18, 50×21 mm, 1.7 mum, Mobile phases: A: H2O +0.1% HCOOH/B: MeCN+0.06% HCOOH. Gradient: t=0 min: 97%A, 3% B, t= O.i min 94%A, 6%B t=0.6min 30%A, 70%B t=1.10min 1%A, 99%B t=1.45 min 97%A, 3%B t=1.50min 97%A ,3%B flow rate: 1 ml/min, UV range wavelength 210-350nm]: R1 = 0.80 min, m/z (ES): 344 [M+H]+, 367 [M+Na]+., 181955-79-3

As the paragraph descriping shows that 181955-79-3 is playing an increasingly important role.

Reference：
Patent; GLAXO GROUP LIMITED; WO2008/148853; (2008); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics