Tag: M.W=200-300

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. 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, A new synthetic method of this compound is introduced below., Formula: C10H15NO2S

Example 3Preparation of 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzene sulfonamide potassium salt using Acetone as a solvent and potassium hydroxide as a base; Acetone (45.0 ml), Potassium hydroxide (1.13 gm) and 4-tert-butylbenzenesulphonamide (1.65 gm) were added at 30 C. and stirred for 5 minutes. 4,6-dichloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidine (3.0 gm) was added at 30 C. and the temperature of the reaction mass was raised to reflux. The reaction mass was stirred at reflux for 6.5 hrs. The reaction mass was cooled gradually to room temperature. Acetone was distilled out from the reaction mass under vacuum below 40 C. Water (30.0 ml) was added to the reaction mass at room temperature and the resulting mass was stirred for 3.0 hrs. The precipitated solid was filtered, washed with water (2¡Á3.0 ml) and dried under vacuum at 55-60 C. for 6.0 hrs to obtain 4.04 gms of 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzene sulfonamide potassium salt. (% Yield: 89%)MS of solid: 564.1 (M+H), 548.1, 514.2, 434.1, 370.0, 352.1, 340.0, 324.1, 249.2, 237.1, 197.6, 182.9

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANDOZ AG; US2012/136015; (2012); A1;,
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Synthetic Route of 6292-59-7, These common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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 solution of substituted acetophenone (72.4mmol) 10 in CH3CN (100mL), Br2 (11.57 g, 72.4 mmol) in CH3CN (20 mL) was addeddropwise. The reaction was stirred at room temperature overnight. Solvent wasconcentrated in vacuum and the residue was diluted with ethyl acetate (150 mL)and washed with brine. The organic layer was dried over anhydrous Na2SO4and evaporated. The resulting solid was triturated with cyclohexane (50 mL) andfiltrated to give alpha-bromoacetophenone 11as a white solid. The aqueous solution of NaN3 (4.71 g, 72 mmol) wasadded to the solution of 11 (60mmol) in CH3OH (80 mL) with stirring and cooling. After 4 h, 200 mLwater was added and a large amout of white precipitate was formed. Compound 12 was obtained by filtration. A mixture of 12 (26.3 mmol), hydrochloric acid (7.98 g, 78.8 mmol) and thecatalytic amount of Pd/C was stirred at room temperature under H2 (1atm) overnight. Solvent was separated from Pd/C by filtration through Celite.The solvent was removed and the resulting residue was triturated with ethylacetate (10 mL) and filtrated to give compound 13. A mixture of 14(29.1 mmol), EDCl (7.5 g, 39.67 mmol), HOBT (5.5 g, 39.67 mmol)and N-methylmorpholine (10.5 g, 105.80 mmol) in anhydrous CH2Cl2(50 mL) proceeded with stirring and cooling for 30 min. The reaction was addedby 13 and stirred at roomtemperature for 10 h. The white solid formed was filtrated to give part ofphenylacetamide 15. The filtrate was washed with waterand dried over anhydrous Na2SO4 and evaporated. Theresidue was chromatographed to give another part of 15. Et3N (10.55 g, 104.38 mmol) was added to asuspension of 15 (12.28 mmo) inacetic anhydride (15.65 g, 153.51 mmol) under nitrogen atmosphere at 0 ¡ãC. The mixture was stirred at 75 for 4 h and concentrated in vacuum. Water and CH2Cl2were added to the residue, and the organic layer was separated, washed withbrine, dried over anhydrous Na2SO4 andconcentrated. The resulting residue was triturated with diethyl ether (20 mL)and filtrated to give 16. To asuspension of 16 (21.87 mmol) inanhydrous CH3OH (120 mL), 28percent sodium methoxide in CH3OH(4.76 g, 22.97 mmol) was added slowly under nitrogen atmosphere at 0 ¡ãC. Thereaction was stirred at the same temperature for 1 h and acetic acid (1.48 g,22.97 mmol) was added slowly. The mixture was concentrated in vacuum and theresidue was diluted with CH2Cl2. The organic layer waswashed with water, dried over anhydrous Na2SO4 andconcentrated in vacuum. The resulting solid was triturated with diethyl ether(30 mL) and filtrated to give 17 as a pale yellow solid. NaH (0.13 g,3.25 mmol) was added to the solution of 17(1.28 mmol) in anhydrous DMF (5 mL) at 0 ¡ãC. The reaction was stirred at the sametemperature for 30 min, diluted with ethyl acetate (100 ml) and washed withwater (3 ¡Á 30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated todryness. 18 was obtained by a silicagel column chromatography as a yellow solid. A mixture of 18 (4.96 mmol), K2CO3 (0.69 g, 4.96 mmol),TBAB (0.16 g, 0.5 mmol) and 1,4-dibromobutane (4.28 g, 19.84 mmol) in CH3CN(20 mL) was stirred at 45 ¡ãC. The solvent was removed and the residue was diluted withethyl acetate (100 mL) and washed with water (3¡Á 30 mL). Theorganic layer was dried over anhydrous Na2SO4and concentrated. Intermediate 19was obtained by a silica gel column chromatography. To a solution of 19 (0.37 mmol) in CH3CN (5mL) were added KI (0.11 g, 0.75 mmol), K2CO3 (0.093 g,0.56 mmol) and substituted aromatic sulfonamide (0.56 mmol ). The reaction wasstirred in the refluxing CH3CN overnight. The solvent wasconcentrated and the residue was diluted with ethyl acetate (50 mL) and washed withbrine. The organic layer was dried over anhydrousNa2SO4 and concentrated in vacuum followed by a silicagel column chromatography to yield compounds 20a-m.

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Xinrui; Lu, Peng; Xue, Xiaojian; Qin, Hui; Fan, Chen; Wang, Yubin; Zhang, Qi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 849 – 853;,
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Synthetic Route of 147291-66-5, A common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, molecular formula is C12H18N2O2, 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.

The solution of EDCI (3.14g, 16.38mmol) and DMAP (100mg, 0.82mmol) in 10mL DCM was added dropwise to a mixture of tert-butyl-3-aminobenzyl-carbamate (2.0g, 9.01mmol) and benzoic acid (1.0g, 8.19mmol) in 20mL DCM at 0C under nitrogen atmosphere, and the mixture was warmed to r.t. and stirred overnight. After quenched with water and extracted with DCM, the organic layer was washed with 1M NaOH (20mL), 1M HCl (20mL), and saturated NaHCO3 (10mL), dried over Na2SO4, and concentrated under reduced pressure. The Boc-protected 12a was dissolved in DCM (5mL), trifluoroacetic acid (5mL) was added. The reaction mixture was allowed to stir for 2hat r.t. and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel and further purified by recrystallization (ethyl ether) to obtain the title compound as a white solid (1.2g, yield 64.8%). 1H NMR (600MHz, DMSO-d6) delta: 10.42 (1H, s), 8.34 (3H, s), 8.01-7.96 (3H, m), 7.70 (1H, d, J=8.4Hz), 7.61 (1H, t, J=8.4Hz), 7.54 (2H, t, J=7.8Hz), 7.41 (1H, t, J=7.8Hz), 7.22 (1H, d, J=7.8Hz), 4.04 (2H, s). 13C NMR (150MHz, DMSO-d6) delta: 166.1, 139.9, 135.2, 134.9, 132.1, 129.4, 128.8, 128.1, 124.4, 121.3, 121.0, 42.9.

The synthetic route of 147291-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Yaxue; Wang, Zhongli; Zhang, Jianchen; Zhou, Huchen; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 178 – 184;,
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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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., COA of Formula: C7H7NO4S

Pathway ii: A mixture of 4-(aminosulfonyl)benzoic acid (4)(2 mmol) and N,N,N,N-tetramethyl-O-(1H-benzotriazol-1-yl)uraniumhexafluorophosphate (HBTU) (2 mmol) in DMF(2 mL) was stirred at room temperature for 1 h. Then, a solution of the appropriate amine derivative (2 mmol) in TEA (2 mmol) was added dropwise. The reaction mixture was left overnight and then quenched with water (10 mL) and extracted with EtOAc (3 5 mL).The organic phase was dried with Na2SO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography(DCM/MeOH 96:4), crystallized by treatment with a mixtureof Et2O and EtOH (1:1) to give the desired final compounds 5b, 5c,6a, 7a-f and 8a-d as white crystals. For compounds 5 a-d, 6a, 8a and 8d registered CAS numbers have been already assigned. However,their synthetic procedures, chemical properties and structural characterization are not available in literature.

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; Buemi, Maria Rosa; Di Fiore, Anna; De Luca, Laura; Angeli, Andrea; Mancuso, Francesca; Ferro, Stefania; Monti, Simona Maria; Buonanno, Martina; Russo, Emilio; De Sarro, Giovanbattista; De Simone, Giuseppina; Supuran, Claudiu T.; Gitto, Rosaria; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 443 – 452;,
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Synthetic Route of 68621-88-5, These common heterocyclic compound, 68621-88-5, name is tert-Butyl (3-aminophenyl)carbamate, 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.

(3-Aminophenyl)carbamic acid tert-butyl ester (1.0 g) was dissolved in ethyl acetate (30ml) and treated with aqueous formaldehyde (37% wt, 443 mul) and palladium on carbon (10%, 350 mg). The reaction mixture was hydrogen- ated under a balloon of hydrogen overnight at atmospheric pressure. The cata- lyst was removed by filtration through Celite under nitrogen and the volatiles were removed by evaporation. The residue was purified by chromatography using the Biotage system on a 10 g silica cartridge eluting with a mixture of ethyl acetate and cyclohexane (1 :19 increasing to 1 :1) to give (3-methylamino- phenyl)carbamic acid tert-butyl ester (500 mg). LCMS (Method A) Rt 2.45 (M+H+) 2231H NMR (300MHz) (CDCI3) delta 7.2 (t, 1 H) 6.8 (br s, 1H) 6.5 (dd, 1 H) 6.4 (br s, 1 H), 6.3 (dd, 1 H) 3.7 (br s, 1 H) 2.8 (s, 3H) 1.5 (s, 9H)

Statistics shows that tert-Butyl (3-aminophenyl)carbamate is playing an increasingly important role. we look forward to future research findings about 68621-88-5.

Reference:
Patent; BIOTIE THERAPIES CORP.; KORHONEN, Jani; MARJAMAeKI, Anne; NISSINEN, Liisa; PIHLAVISTO, Marjo; WO2010/146236; (2010); A1;,
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1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 1103234-56-5

Step A: Diphenylphosphonic azide (9.082 mL, 0.04214 mol) was added to stirred solution of 2,6-difluoro-3-(propylsulfonamido)benzoic acid (10.234 g, 0.036647 mol) and triethylamine (11.75 mL, 0.08429 mol) in tetrahydrofuran (100 mL, 1 mol) and the reaction mixture was stirred at room temperature for 3 hours and then heated to reflux for an additional hour. lH-pyrazole (2.5 g, 0.037 mol) was added to the reaction mixture, followed by heating to reflux for 1 additional hour. After cooling to room temperature and removal of the solvent under reduced pressure, an orange-colored oil was obtained. This crude material was purified by silica gel chromatography; eluent: 0-50% ethyl acetate: heptane. The obtained material was recrystalized from 150 mL of a solution of ethyl acetate / heptane (1:3, v/v) to give N-(2,6- difluoro-3-(propylsulfonamido)phenyl)-lH-pyrazole-l-carboxamide with 90% purity (4.4 g, 87%). 1H NMR (500 MHz, DMSO-d6) delta 10.33 (s, IH), 9.70 (s, IH), 8.41 (d, J=2.6, IH), 7.92 (d, J=Ll, IH), 7.42 (td, J=8.9, 5.8, IH), 7.22 (t, J=9.2, IH), 6.62 (dd, J=2.7, 1.6, IH), 3.13 – 3.03 (m, 2H), 1.80 – 1.70 (m, 2H), 1.04 – 0.93 (m, 3H). LC/MS: m/z 345.2 [M+l].

The synthetic route of 1103234-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; PULK, Rebecca; RUDOLPH, Joachim; WEN, Zhaoyang; WO2011/25965; (2011); A1;,
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Related Products of 28460-30-2,Some common heterocyclic compound, 28460-30-2, name is 2,4,6-Trichlorobenzenesulfonamide, molecular formula is C6H4Cl3NO2S, 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 solution of 500 mg of 6-(4-amino-phenyl)-1H-pyrazolo[3,4-b]pyrazin-3-ylamine hydrochloride and 397 mg of 2-fluoro-5-methyl-benzenesulfonyl chloride in 4 ml DCM, 0.16 ml pyridine were added and the reaction mixture was stirred for 16 h at RT. Then, the solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/EtOAc. The fractions containing the product were combined and the solvent evaporated under reduced pressure. The title compound was prepared by adapting the procedures described in example 19, employing 2,4,6-trichlorobenzenesulfonamide instead of 2-fluoro-5-methyl-benzenesulfonyl chloride. MS (ES+): m/e = 470.1 (M+H), chloro pattern.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6-Trichlorobenzenesulfonamide, its application will become more common.

Reference:
Patent; SANOFI; Nazare, Marc; Halland, Nis; Schmidt, Friedemann; Weiss, Thilo; Hofmeister, Armin; EP2570415; (2013); A1;,
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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. 114790-39-5, name is Benzyl (2,2-dimethoxyethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Benzyl (2,2-dimethoxyethyl)carbamate

BenzvK ( 6-chloro-2-( 3-chlorobenzoyl)-2, 3, 4,9-tetrahvdro-lH-pyridoi 3, 4-b lindol- l-yl)methyl) carbamate trifluoroacetic acid: To a mixture of benzyl (2,2-dimethoxyethyl)- carbamate (1.71 g, 7.15 mmol) in 2-butanol (30 mL) was added 2-(5-chloro-lH-indol-3-yl)ethan- l-amine (l.53g, 7.86 mmol), TFA (0.74 g) and LEO (1 mL) The mixture was stirred at 100 C for 16 hrs. Then the reaction was cooled to room temperature. The precipitates were collected via filtration to afford benzyl((6-chloro-2-(3-chlorobenzoyl)-2,3,4,9-tetrahydro-lH-pyrido[3,4- b]indol-l-yl)methyl)carbamate trifluoroacetic acid (3.5g, yield: 98.9%) as a white solid. LCMS: [M+H]+= 370.1.

The synthetic route of 114790-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RECREO PHARMACEUTICALS LLC; ZHANG, Jing; WANG, Xiang; PODOLL, Jessica, D.; (207 pag.)WO2020/37155; (2020); A1;,
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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. 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

3,8-diazabicyclo [3.2.1] octane-3-carboxylic acid tert-butyl ester (318 mg, 1.5 mmol)And 2-chloro-5- (chloromethyl) erythropine (243 mg, 1.5 mmol) were dissolved in acetonitrile (50 mL)Potassium carbonate (414 mg, 3.0 mmol) was added and reacted at 70 C for 16 hours.After cooling to room temperature, ethyl acetate (10 mL) and water (50 mL) were added,The aqueous phase was extracted with ethyl acetate (150 mL X3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (480 mg, 95% yield) as a pale yellow oil.

The synthetic route of 201162-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu, Yongqian; (45 pag.)CN104910137; (2017); B;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H10N2O3S

2 mmol compound 1a or 1b and 0.194 g (2 mmol) potassiumthiocyanate in about 25 mL acetone were refluxed for 30 min. Theresulting solid (KCl) was removed by filtration. Then to this solutioncorresponding sulfonamides (2 mmol) in about 10 mL acetone wasadded dropwise, the mixture was stirred under reflux for 2 h. The resulting solution was evaporated under reduced pressure. Then,the residue was treated with the water to give crude product as awhite solid. The resulting crude product was stirred with diethyletherat room temperature for 1 h and then filtered. After theseexperimental procedures, the white colored substance was obtainedas pure.

According to the analysis of related databases, 144-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koca, ?rfan; Yi?itcan, Serhat; Guemue?, Mehmet; Goekce, Halil; Sert, Yusuf; Journal of Molecular Structure; vol. 1204; (2020);,
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