Tag: M.W=200-300

Synthetic Route of 33545-97-0, A common heterocyclic compound, 33545-97-0, name is N,N’-Di-Boc-1,4-butanediamine, molecular formula is C14H28N2O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Commercially available putrescine 1 is (bis)-N-Boc protected to produce compound 2 (85.2% yield). Compound 2 is used to alkylate qty. 2 equivalents of propargyl bromide in the presence of sodium hydride producing compound 3 (59.5% yield). Yields in that transformation are further enhanced by using a mixture of dimethylformamide (“DMF”) and tetrahydrofuran (“THF”) in a ratio of 1:5. The propargyl groups in compound 3 are converted to the corresponding allenes in the presence of CuBr, formaldehyde, and diisopropylamine to yield intermediate compound 4 (38.7% yield). Compound 4 is de-protected in the presence of HCl to yield the desired target molecule MDL 72,527 (white solid, 65.8% yield). [00097] HPLC method of quantitation of MDL, natural polyamines and their acetyl derivatives in cell extracts as well as in human and animal serum is standardized. Therefore, the pharmacokinetics and pharmocodynamics of MDL 72,527 may be determined.

The synthetic route of 33545-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; WO2007/130589; (2007); A2;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 35303-76-5, HPLC of Formula: C8H12N2O2S

General procedure: Starting dichlorotriazinyl benzenesulfonamide (1 mmol; 0.320 g of4- [(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzene-1-sulfonamide, 0.334 g of4-{[(4,6-dichloro-1,3,5-triazin-2-yl)amino]methyl}benzene-1-sulfonamide or 0.348 g of4-{2-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-ethyl}benzene-1-sulfonamide)) was dissolved in20 mL of DMF. Then 1 mmol (0.138 g) of solid anhydrous potassium carbonate was added in smallportions and the mixture was stirred for 10 min. Then 1 mmol of the appropriate nucleophile wasadded portion wise. Finally, 2.5% mol. of supported Cu(I) ions (312 mg of catalyst) was addedinto the reaction mixture. Reaction was stirred at 35 C until the maximum conversion of startingmaterial is achieved (monitored by TLC). After completion of the first reaction step, 1 mmol of thesecond nucleophile and 1 mmol (0.138 g) of anhydrous potassium carbonate were added into thereaction mixture. The reaction mixture was then stirred at 100 C until the maximum conversion of anucleophile was determined (monitored by TLC). After completion of a reaction, the catalyst andsalt were filtered o. Crushed ice was then added into the solution and the formed precipitate wascollected by filtration. The crude product was dissolved in acetone and precipitated by the addition ofisopropyl alcohol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Aminoethyl)benzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Article; Havrankova, Eva; Csoellei, Jozef; Pazdera, Pavel; Molecules; vol. 24; 19; (2019);,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Example 257B 5-(1-Phenyl-1H-pyrazol-4-yl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid tert-butyl Ester To the product of Example 6C (0.5 g, 2.4 mmol) in 15 mL toluene in a pressure tube was added the product of Example 257A (0.68 g, 3.06 mmol), tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, Strem, 43 mg, 0.047 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, Strem, 59 mg, 0.094 mmol), and tert-BuONa (0.362 g, 3.8 mmol). This mixture was warmed to 85 C. and stirred for 18 h. At this point, the reaction was incomplete, so additional Pd2(dba)3 (43 mg, 0.047 mmol) and BINAP (59 mg, 0.094 mmol) were added and the mixture stirred for an additional 24 h. The reaction was cooled to ambient temperature, filtered through Celite diatomaceous earth, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 50% hexanes-EtOAc) to give the title compound (40 mg, 0.113 mmol, 5% yield). MS (DCl/NH3) m/z 355 (M+H)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; Mortell, Kathleen H.; Nersesian, Diana L.; Schrimpf, Michael R.; US2005/101602; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 201162-53-0, Recommanded Product: 201162-53-0

Tertbutyl 3,8-diazabicyclo[3 .2.ljoctane-3-carboxylate (250 mg, 1.18 mmol), 5-bromopicolinic acid (0.309g, 1.53 mmol), sodium 2-methylpropan-2-olate (0.283 g, 2.94 mmol), methanesulfonato(2-dicyclohexylphosphino-2?,6?-di-i-propoxy- 1,1 ?-biphenyl)(2-amino- 1,1biphenyl-2-yl)palladium(II) (0.04 9 g, 0.05 9 mmol) and 1 ,4-dioxane (4 mL) were charged in a vial. The headspace was flushed with nitrogen and the reaction mixture was degassed using 4 cycles of vacuum and nitrogen refilling. The reaction was heated at 110 C for 36 h then cooled to room temperature. Silica gel was added and the solvent was removed under vacuum. The desired product was purified by silica gel chromatography (eluting with hexane/ ethyl acetatemethanol). LCMS M/Z (M+H) 334.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Boc-3,8-Diazabicyclo[3.2.1]octane, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 456-64-4, Formula: C7H6F3NO2S

EXAMPLE 50 3-Methyl-2-[5-(trifluoromethanesulfonamido)pentan-1-ylthio]-1,4,7b-triazacyclopent[cd]indene To a solution of 500 mg (1.82 mmol) of 3-methyl-2-[5-(amino)pentan-1-ylthio]-1,4,7b-triazacyclopent[cd]indene in 30 ml of acetonitrile were added 0.51 ml (3.66 mmol) of triethylamine and 1.302 g (3.66 mmol) of N-phenyltrifluoromethanesulfonamide. The mixture was stirred for two hours at room temperature. The solvent was distilled off. To the residue was added methylene chloride, which was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to afford 608 mg (82.1%, a pale yellow solid) of the desired compound. NMR(200 MHz,CDCl3)delta: 1.55-1.85(4H,m), 1.97(2H,m), 2.90(3H,s), 3.39(2H,m), 3.50(2H,t,J=7.0 Hz), 7.69(1H,d,J=7.8 Hz), 7.73(1H,d,J=8.0 Hz), 7.95(1H,dd,J=8.0, 7.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1,1-Trifluoro-N-phenylmethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5958942; (1999); A;,
Amide – Wikipedia,
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Electric Literature of 40724-47-8, A common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, molecular formula is C7H8BrNO2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a mixture of correspondingbromide (1.1 equiv) in 4 mL DMSO was added NaN3 (24 mg, 0.37 mmol).The mixture was stirred at room temperature for 1 h, and the 4mL H2O, sodium ascorbate (29 mg, 0.15 mmol),intermediate 5 (100mg, 0.37 mmol)and CuI (14 mg, 0.07 mmol). The reaction mixture was stirred at roomtemperature overnight, and extracted with ethyl acetate. The extract was driedover anhydrous MgSO4, and concentrated under reduced pressure. Theresidue was purified by silica gel column chromatography with dichloromethane/methanol (10:1) to affordthe desired products 1 and 6-32, respectively.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Li, Jia-Cheng; Zhang, Juan; Rodrigues, Mosar Correa; Ding, De-Jun; Longo, Joao Paulo Figueiro; Azevedo, Ricardo Bentes; Muehlmann, Luis Alexandre; Jiang, Cheng-Shi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 3881 – 3885;,
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Related Products of 1346674-23-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1346674-23-4, name is 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0298] Example 10B (0458) [0299] Compound 170 was prepared from compounds 160 and 100 as follows: (0459) (0460) [0300] Potassium carbonate (20.3 g, 1.5 eq., 147 mmol), compound 100 (19 g, 1.1 eq., 108 mmol), compound 160 (20 g, 1 eq., 97.9 mmol), DPPF ligand (2.2 g, 0.04 eq., 3.9 mmol), and Pd(OAc)2 catalyst (0.44 g, 0.02 eq., 2 mmol) were charged to a reactor. THF (200 mL, 10 mL/g) was charged to the reactor with agitation. The reactor was evacuated and filled with N2 three times and the contents were then heated to 68C with reflux. The reactor was sampled at 22 hours and the compound 160 content was 0.9 area% by HPLC. The reactor contents were cooled to 65C and water (200 mL, 10 mL/g) was charged to the reactor over 4 hours and the reactors contents were then held at 20C for a minimum of 3 hours. The reactor contents were filtered and compound 170 was collected as a solid. The solid compound 170 was rinsed with THF/water (1 : 1 mixture, 200 mL, 10 mL/g). The washed solids were dried under vacuum with N2 purge at 22 C for a minimum of 3 hours. A yield of 84% was obtained with 99 area% by HPLC (245 nm), 79 ppm Pd and 0.2% residue on ignition (“ROI”). Of the impurities, 0.51 A% regioisomer and 0.33%> bis-coupling product were found: (0461) (0462) Regioisomer Bis-Coupling Impurity (0463) [0301] The method was repeated on a 40 g scale (based on compound 160). The coupling reaction was performed using compound 100 (1.1 eq.), Pd(OAc)2 (0.02 eq.), dppf in THF (0.04 eq., 10 mL/g) at 68 C for 28 h to reach 98.4% conversion. Water was added (350 mL) to the reaction mixture over 3 h and aged at 65 C for 10 h, cooled to 20 C in 1.5 h and aged for 16 h. After filtration and drying, a beige solid compound 170 was obtained (57.2 g, 85%, 98.6A%, 0.55A% regioisomer, 0.48A% bis-coupling impurity, 87 ppm Pd and 0.3% ROI). (0464) [0302] The method was repeated on a 609 g scale (based on compound 160). (0465) Potassium carbonate (0.6114 kg, 1.5 eq., 4.34 mol), compound 100 (0.7769 kg, 1.5 eq., 4.41 mol), compound 160 (0.6099 kg, 1 eq., 2.99 mol), DPPF ligand (0.0662 kg, 0.04 eq., 0.119 mmol), and Pd(OAc)2 catalyst (0.0137 kg, 0.02 eq., 0.061 mmol) were charged to an isolator. A reactor was evacuated and filled with N2 three times and charged with the contents of the isolator. THF (10.35 kg, 20 L/kg) was charged to the reactor with agitation. The reactor contents were heated to 68C with reflux. The reactor was sampled at 40 hours and the compound 160 content was 0.3 area% by HPLC. The reactor contents were cooled to 65C and water (6.01 kg, 10 L/kg) was charged to the reactor over 3 hours and the reactor contents were then held at 20C for a minimum of 3 hours. The reactor contents were filtered and compound 170 was collected as a solid. The solid compound 170 was rinsed with THF/water (1 : 1 mixture, 6 L, 10 mL/g). The washed solids were dried under vacuum with N2 purge at 22C for a minimum of 10 hours. A 84% yield (0.8576 kg) was obtained with 99.2 A% by HPLC (245 nm), 24 ppm Pd and less than 0.1% ROI.

The synthetic route of 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BEAUDRY, Danial; CRAVILLION, Theresa; GOSSELIN, Francis; LIM, Ngiap-Kie; MALHOTRA, Sushant; TIAN, Qingping; ZHANG, Haiming; GMEHLING, Alexander; FETTES, Alec; BACHMANN, Stephan; (130 pag.)WO2018/109050; (2018); A1;,
Amide – Wikipedia,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 79722-21-7, name is tert-Butyl benzyloxycarbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl benzyloxycarbamate

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

The synthetic route of 79722-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
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Related Products of 207405-68-3,Some common heterocyclic compound, 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H22N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Azabicyclic amine (7a-c, 1.2 mmol) and Hunig?s base (4.0 mmol) were added to a solution of compound (4or 5, 1.0 mmol) in n-BuOH (2 ml) and the resulting mixture was stirred at reflux for 1 day. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was purified by column chromatography (CHCl3/MeOH 200:1) to obtain product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, its application will become more common.

Reference:
Article; Pham, Tuan-Anh N.; Yang, Zunhua; Fang, Yuanying; Luo, Jun; Lee, Jongkook; Park, Haeil; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1349 – 1356;,
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Electric Literature of 1314538-55-0,Some common heterocyclic compound, 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, molecular formula is C6H12BF3KNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

102201 Into a reaction vessel was placed, compound 14-4, prepared in accordance with Example13, (52 mg, 0.1 mmol), commercial Potassium N-Boc-amino-methyltrifluoroborate (47 mg, 0.2 mmol), Cs2CO3 (97 mg, 0.3 mmol), Pd(dppf)C12 CH2C12 Adduct (8.1 mg, 9.93 jimol) dissolved in degassed water (0.5 ml) and 1 ,4-dioxane (5 ml). The mixture was heated to 90 C overnight, cooled to room temperature (rt) and diluted with EA, then washed with water brine and dried over Na2504. After filtration and concentration, the crude residue was taken up with DCM (5 mL), then TFA (1 mL) was added. The mixture was stirred at rt for 1 hour and concentrated. The concentrate was purified by reverse phase chromatography (5-75% MeCN in water w/ 0.1% TFA, C 18 column) to yield 19-1 as the TFA salt. ?H NMR oe (ppm)(DMSO-d6): 7.89 (1 H, d, J = 5.79 Hz), 7.71-7.77 (2 H, m), 7.46 (1 H, t, J = 7.75 Hz), 7.37 (1 H, d, J = 7.65 Hz), 7.09 (1 H, d, J = 10.04 Hz), 6.92 (1 H, dd, J = 7.92, 1.98 Hz), 6.58 (1 H, dd, J = 8.02, 2.48 Hz), 5.88-5.93 (1 H, m), 4.24- 4.33 (2 H, m), 2.45 (3 H, s), 1.93 (3 H, d, J = 7.08 Hz). HRMS C22H20F2N4045 [M+H] calc:475.1246, obs: 475.1242

The synthetic route of 1314538-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PERO, Joseph, E.; LEHMAN, Hannah, D. G. F.; KELLY, Michael, J., III; ZHAO, Lianyun; ROSSI, Michael, A.; LI, Dansu; GILBERT, Kevin, F.; WOLKENBERG, Scott; MULHEARN, James; LAYTON, Mark, E.; DE LEON, Pablo; WO2014/66490; (2014); A1;,
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