Category: 402-46-0

These common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, 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. Quality Control of 4-Fluorobenzenesulfonamide

Example 44; 4-{2-[4-(4-Sulfamoylphcnyl)pipcrazin-l-yl]cthyl}pipcridinc-l-carboxylic acid tert-butyl ester hydrochloride; EPO A mixture of 4-fluorobenzenesulfonamide (1.00 g, 5.71 mmol) and piperazine (2.46 g, 28.54 mmol) in water (12 mL) was heated at 1000C for 2Oh. The resulting precipitate was collected filtration and washed with water and toluene to give 4-piperazin-l- ylbenzenesulfonamide: RT = 0.49 min; m/z (ES+) = 242.13 [M+H]+. A solution of 4-piperazin- 1-ylbenzenesulfonamide (0.46 g, 1.89 mmol) and 4-(2-oxoethyl)piperidine-l-carboxylic acid tert-butyl ester (0.43 g, 1.89 mmol) in DCM (50 mL) and THF (7 mL) with molecular sieves (0.90 g) was stirred under argon at rt for Ih. Sodium acetoxyborohydride (0.52 g, 2.46 mmol) was added and the reaction mixture was stirred for a further 2.5h. The reaction mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4) and the solvent was removed under vacuum. The resulting solid was purified by recrystallisation (EtOAc) then dissolved in THF and 1 M HCl in dioxane (0.95 equivalents), the solvent was removed under vacuum and the resulting solid was washed with Et2O to afford the title compound: RT = 2.51 min; m/z (ES+) = 453.33 [M+H]+.

The synthetic route of 4-Fluorobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROSIDION LIMITED; WO2007/3964; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, name is 4-Fluorobenzenesulfonamide, 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. Formula: C6H6FNO2S

Synthesis Example 6 Synthesis of N-(4-fluorophenylsulfonyl)-2-chloro-6-methoxyisonicotinamide (Compound No. 38) 1.75 g (0.01 mol) of 4-fluorobenzenesulfonamide were dissolved in 30 ml of pyridine, and added dropwise by 2.06 g (0.01 mol) of 2-chloro-6-methoxyisonicotinoyl chloride at 0 C. to 5 C., followed by agitation for 2 hrs. at room temperature. After acidified by adding aqueous hydrochloric acid, the precipitate was extracted by ethyl acetate. The organic layer obtained was dried and them concentrated to precipitate crude crystals, which were recrystallized by n-hexane/ethylacetate to 2.1 g (yield: 61.0%) of N-(4-fluorophenylsulfonyl)-2-chloro-6-methoxy isonicotinamide as white crystal.

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Kayaku Kabushiki Kaisha; US4690934; (1987); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, 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. Safety of 4-Fluorobenzenesulfonamide

EXAMPLE 11; Preparation of racemic (2’S, 3S, 4’R)-6-chloro-4′-{5-chloro-2-[1-(4-fluoro-benzenesulfonylaminocarbonyl)-cyclobutoxy]-phenyl}-2′-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione; A solution of racemic (2’S, 3S, 4’R)-6-chloro-4′-[5-chloro-2-(1-hydroxycarbonyl-cyclobutoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (50 mg, 0.086 mmol) and CDI (28 mg, 0.17 mmol) in DMF (0.5 mL) was heated at 60 C. for 30 min, and then cooled to root temperature. To this solution was added a mixture of 4-fluoro-benzenesulfonamide (175 mg, 1 mmol) and NaH (40 mg, 60%, 1 mmol) in DMF (1 mL). The resulting mixture was stirred at room temperature for 10 min, purified by prep-HPLC to give the title compound as a white solid (20 mg).

The synthetic route of 4-Fluorobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 402-46-0 as follows. name: 4-Fluorobenzenesulfonamide

General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 ¡Á 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Yin; Qiu, Ke-Ming; Lu, Xiang; Liu, Kai; Fu, Jie; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4730 – 4738;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 402-46-0, A common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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.

Example 13; 4-Fluoro-{N-4-[N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino]- benzoyl} benzenesulfonamide; A mixture of 4- [N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino] benzoic acid (50 mg, 0.14 mmol), 4-fluorobenzenesulfonamide (49 mg, 0. 28 mmol), 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (54 mg, 0.28 mmol), and dimethylaminopyridine (35 mg, 0.28 mmol) was taken up in dichloromethane (1 mL) and stirred for 18h. The mixture was partitioned between EtOAc (50 mL) and 20% aqueous NH40Ac. The EtOAc was separated, washed with brine, dried (MgS04) and concentrated. The residue was purified by column chromatography (silica gel) eluting with 100% EtOAc to give 38 mg of 4-fluoro-f N 4- [N (3-fluoro-4- methoxyphenyl)-pyridin-3-ylmethylamino]-benzoyl} benzenesulfonamide as a white solid. IH NMR (300 MHz, CDC13) 6 8.5-8. 4 (m, 2H), 8. 11 (m, 2H), 7.7-7. 5 (m, 3H), 7.25 (m, 1H), 7.16 (m, 2H), 7.0-6. 8 (m, 3H), 6.63 (d, J=9.0, 2H), 4.92 (s, 2H), 3.89 (s, 3H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/61458; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, name is 4-Fluorobenzenesulfonamide, 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. HPLC of Formula: C6H6FNO2S

To a solution of 4-fluorobenzenesulfonamide (1 .02 g, 5.71 mmol) in H20 (10 mL) was added piperazine (2.46 g, 28.55 mmol). The reaction mixture was stirred at 100 00 overnight. The mixture was cooled to room temperature and filtered. The filtration cake was washed with H20 (20 mL), toluene(30 mL) and ether (30 mL) to give 26.1 (401 mg, 29% yield). MS (ESI) m/z = 242.0 [M¡ÂH]. 1H NMR (400 M, DMSO-c), oe 7.60 (d, J = 8.8 Hz, 2H), 7.05 (m, 2H), 7.00 (d, J = 8.8 Hz, 2H), 3.17 (m, 4H), 2.80 (m, 4H), 2.33 (m, 1H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNITY BIOTECHNOLOGY, INC.; BACKES, Bradley; W. VON GELDERN, Thomas; CHEN, Bing; (121 pag.)WO2017/101851; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, Adding a certain compound to certain chemical reactions, such as: 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 402-46-0.

General procedure: A solution of compound 9, 12a-12g or 16a-16g (1.0eq),substituted sulfonyl chloride (1.1eq) or substituted acyl chloride(1.1eq) and TEA(1.5eq) were added into DMF(5 ml. And then themixture was stirred at room temperature for 6 h. Upon completion,ethyl acetate (20 ml) and H2O (5 ml) were added. The aqueous layerwas extracted with ethyl acetate for several times, the combinedorganic layers were washed with H2O for several times, and thenwashed with brine, dried over MgSO4 and evaporated to give theproducts. The crude residue was purified by silica gel columnchromatography eluted with a mixture of petroleum ether andethyl acetate (2:1) to obtain target compound.

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jian-Song; Gao, Qiu-Lei; Wu, Bo-Wen; Li, Dong; Shi, Lei; Zhu, Ting; Lou, Jian-Feng; Jin, Cheng-Yun; Zhang, Yan-Bing; Zhang, Sai-Yang; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, 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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below.

Step 1. A mixture of 4-fluorobenzenesulfonamide (1 equiv.), tert-butyl N-(azetidin- 3-yl)carbamate (1.3 equiv.), and diisopropylethylamine (1.3 equiv.) was stirred in acetonitrile at 150 C for 1 h in a sealed vial. The reaction mixture was then concentrated and purified by silica gel chromatography using MeOH (0 – 9%) in DCM.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 402-46-0 as follows. 402-46-0

A round bottom flask was charged with 4-fluorobenzenesulfonamide (945 mg, 5.4 mmol), L-proline-t-butyl ester HCl (1.24 g, 6 mmol), and cesium carbonate (4.2 g, 12 mmol) and suspended in 10 ml anhydrous DMSO. The mixture was placed in a preheated oil bath and equipped with a condenser, and heated under nitrogen at 168 oC overnight. HPLC analysis of the mixture indicated complete conversion of the benzenesulfonamide starting material. The mixture was transferred to an Erlenmeyer flask, the reaction pot was diluted with 2 ml of concentrated HCl, and added to the mixture in the Erlenmeyer flask and allowed to stir. The aqueous was then extracted with ethyl acetate (3 x 50 ml), and the combined extracts were washed with water (3 x 15 ml). The volatiles were then removed under vacuum, and 1.24 g of crude material was obtained. The desired intermediate was isolated using MPLC, utilizing a 0 to 60% gradient of acetone in DCM, affording 0.56 g (41%):1H NMR (300 MHz, DMSO-d6)d ppm 7.58 (d, J= 9.0 Hz, 2H), 6.98 (s, 2H), 6.54 (d, J= 9.0 Hz, 2H), 4.28 (d, J= 8.4 Hz, 1H), 2.35-2.22 (m, 2H), 2.04-1.96 (m, 2H).

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ahmed, Gulzar; Elger, Walter; Meece, Frederick; Nair, Hareesh B.; Schneider, Birgitt; Wyrwa, Ralf; Nickisch, Klaus; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5569 – 5575;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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. 402-46-0

Example 10 27. N-(4-fluorobenzene)sulfonyl-alpha-dehydrovaline.; 3-methyl-2-oxobutyic acid, sodium salt (5.0 g, 36.2 mmol) was slurried in MTBE (25 mL) and cooled to 0 C, then HCI (12.1 N, 3.1 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (25 mL). The combined organics were stripped to give a light-yellow oil. This oil was dissolved in toluene (35 mL) and diethyleneglycol diethyl ether (5 mL) and p-toluenesulfonamide (5.1 g, 29.0 mmol) then methanesulfonic acid (0.19 mL, 2.9 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to 5 C. The resulting solid was filtered, and dried to give 5.4 g of crude material, which was recrystallized from MeOH/ water (16 mL/ 38 mL) to give 4.90 g of pure white solid (62% isolated yield). mp 172-173 C. IH-NMR (400 MHz, CD30D) d 7.83-7.86 (m, 2H), 7.22-7.27 (m, 2H), 2.12 (s, 3H), 1.87 (s, 3H); ?3C NMR (100 MHz, CD30D) 166.6,166.3, 163.7, 151.6, 136.7 (2 peaks), 129.9,129.8, 120.8, 115.5, 115.3, 22.0, 20.4 ppm. HRMS calcd for C11H11FNO4S (M-H) : 272.0393, Found: 272.0398.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 402-46-0, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2005/118529; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics