Category: amides-buliding-blocks

Synthetic Route of 6325-93-5,Some common heterocyclic compound, 6325-93-5, name is 4-Nitrobenzenesulfonamide, molecular formula is C6H6N2O4S, 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: The catalytic reduction of nitro aromatics was conducted in a 25 mlTelfon-lined stainless steel autoclave with magnetic stirring. In a typicalprocess, 6 mmol nitroarene, and desired amounts of reducing agent andsolvents were introduced in the reactor. The autoclave was transferredinto a water bath at the set temperature with an accuracy of better than0.2 C for ?0.5 h. Then, 10 mg catalyst was added into the reactionmixture and started the reduction at a stirring rate of 450 rpm. After thereaction, the catalyst was rapidly separated by ltration. n-Decane(500 muL) as standard was added into the ltrate and was dried withanhydrous Na 2 SO 4 . The products were analyzed by gas chromato-graphy-mass spectrometry (GC-MS) (Shimadzu GCMS-QP2010 Plus)and GC (Varian CP-3800) with a capillary column (column VF-1 ms,15 m, 0.25 mm, 0.25 mum) and a ame ionization detector (FID).

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

Reference:
Article; Huang, Haigen; Liang, Xiangcheng; Wang, Xueguang; Sheng, Yao; Chen, Chenju; Zou, Xiujing; Lu, Xionggang; Applied Catalysis A: General; vol. 559; (2018); p. 127 – 137;,
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Related Products of 40724-47-8,Some common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, molecular formula is C7H8BrNO2S, 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.

4-Azidomethyl-benzenesulfonamide (INT-2); To a stirred solution of 4-bromomethyl-benzenesulfonamide (4.500 g,17.9917 mmol) (prepared from 4-bromomethyl-benzenesulfonyl chloride upon treatment with ammonia (as described by Yee YK et al. in Journal of Medicinal Chemistry 1990 33 (9) 2437-2451 ) in lambda/,lambda/-dimethylformamide (30 ml), sodium azide is added (1 1 .696 g, 179.917 mmol) and the reaction mixture is heated at 900C for 14 hours under a nitrogen atmosphere. The suspension is filtered, to remove the excess of sodium azide, and the solid residue is washed with ethyl acetate (4 x 50 ml). The mother liquids are concentrated, to afford a crude yellow liquid (3.820 g, 100% mass balance), that is used as such for the next step. IR: 2098.8 cm”1.

The synthetic route of 40724-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROSEARCH A/S; WO2009/112459; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 703-12-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 703-12-8 name is 4-Bromo-N-methylbenzenesulfonamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step b: 4-(lambdar-Methylsulfamoyl)phenylboronic acid; To a solution of 4-bromo-iV-methyl-benzene sulfonamide (24.9 g, 0.1 mol) and B(O1Pr)3 (28.2 g, 0.15 mol) in THF (200 mL) was added n-BuLi (100 mL, 0.25 mol) at -70 0C. The mixture was slowly warmed to 0 0C, then 10% HCl solution was added until pH 3-4. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and evaporated under reduced pressure to give 4-(iV-methylsulfamoyl)phenylboronic acid (22.5 g, 96%), which was used in the next step without further purification. 1H NMR (DMSO-J6, 300 MHz) delta 8.29 (s, 2 H), 7.92 (d, J = 8.1 Hz, 2 H), 7.69 (d, J = 8.4 Hz, 2 H), 2.36 (d, J = 5.1 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-N-methylbenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/56341; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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. Computed Properties of C7H9NO3S

General procedure: Under the argon atmosphere, a Schlenk tube (15 mL) equipped with a magnetic bar was loaded with the sulfonamide 1 (0.5 mmol), sodium arylsulfinates 2 (0.6 mmol, 1.2 equiv.), Pd(MeCN)2Cl2 (6.5 mg, 5 mol%) and AgOAc (166.9 mg, 1.0 mmol) in one portion. Then, the mixture of 1,4-dioxane/DMSO (3.5 mL in a 9:1 ratio) was added to obtain a clear solution and the reaction mixture was allowed to stir at 120 C for 24 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a petroleum ether and ethyl acetate (3/1) as eluent to give the N-aryl sulfonamides 3 in noted yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1129-26-6, its application will become more common.

Reference:
Article; Zhao, Zijian; Lian, Yan; Zhao, Chang; Wang, Bing; Synthetic Communications; vol. 48; 12; (2018); p. 1436 – 1442;,
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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. 2618-96-4, name is Dibenzenesulfonimide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

General procedure: To a solution of N-sulfonylsulfonamide 1 (1.68 mmol) in N,N-disubstituted formamide 3 (3.0 mL) was added TsCl (2; 0.160 g, 0.840 mmol; 0.480 g, 2.52 mmol for products 4d-g) and Et3N (0.29 mL, 2.10 mmol). The mixture was stirred at r.t. (or heated to 100 C in the cases of 4d-g,k). After the starting material was consumed as indicated by TLC, the reaction mixture was poured into H2O and extracted with CH2Cl2. The combined organic phases were washed with H2O, dried (anhydrous MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified, if necessary, by silica gel flash column chromatography (hexane/EtOAc) to give the desired product as a white solid (Table 2).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2618-96-4.

Reference:
Article; Jeong, Yuri; Ban, Jaeyoung; Lim, Minkyung; Rhee, Hakjune; Synthesis; vol. 50; 9; (2018); p. 1867 – 1874;,
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. 1015-89-0, name is Phenanthridin-6(5H)-one, A new synthetic method of this compound is introduced below., SDS of cas: 1015-89-0

The 5,6-dihydro-phenanthridine (Ik) was prepared using the following procedure: Into a 500 mL round bottom flask equipped with a magnetic stir bar and a reflux condensor was placed 6(5H)-Phenanthridinone (1000 mg, 5123 mumol), THF (250 mL) (fine suspension). The flask is sparged with nitrogen, 2M BH3-dimethylsulfide complex in THF (10 mL) is added. This is allowed to stir at reflux for 24 hours. TLC shows reaction still incomplete (1/1, ethyl acetate/heptane). Solvents removed under reduced pressure. Water (50 mL) and ethyl acetate (100 mL) added. The aqueous layer is separated with ethyl acetate (3 x 100 mL). The organic layers are combined, dried(sodium sulfate), solids removed by filtration, and the solvents removed under reduced pressure. This is purified by silica column chromatography using heptane to 50percent ethylacetate in heptane. The best fractions are pooled and the solvents are removed under reduced pressure to afford an off-white solid (270 mg, Yield: 29percent). LC-MS shows mass 182 (M+H)+.

The synthetic route of 1015-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2008/96001; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1259224-00-4, name is tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate, 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 1259224-00-4, Safety of tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate

To the solution of 2,4-Dichloro-6-methyl-5-nitro-pyrimidine (2.08 g, lO.OOmmol) in THF (50 mL) at -78 C was slowly added the solution of [l-(4-Amino-phenyl)- cyclobutyl]-carbamic acid tert-butyl ester (2.62 g, 10.00 mmol) in THF (20 mL). The reaction mixture was stirred at ambient temperature for 30 min.. Then it was concentrated to remove the solvent. The obtained residue was dissolved in ethyl acetate (250 mL) and washed by saturated. NaHC03 solution, followed by brine. The separated organic layer was dried over sodium sulfate, filtered and concentrated to give { l-[4-(2-Chloro-6-methyl-5-nitro-pyrimidin-4-ylamino)-phenyl]- cyclobutyl}-carbamic acid tert-butyl ester. (4.3 g, 98%yield). MS (ESI+) e/z: 370.9 / 372.9 [M+l]+.

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; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6325-93-5, name is 4-Nitrobenzenesulfonamide, 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 6325-93-5, COA of Formula: C6H6N2O4S

Step 1 – Tert-butyl N-(4-nitrophenyl)sulfonylcarbamate (0596) [00375] To a solution of 4-nitrobenzenesulfonamide (5.00 g, 24.7 mmol) in anhydrous dichloromethane (40 mL) was added triethylamine (5.00 g, 49.4 mmol) and catalytic amount of N,N-dimethylpyridin-4-amine. The mixture was cooled to 0 C and di-tert-butyl dicarbonate (5.67 g, 25.9 mmol) was added over 10 min. Then the mixture was warmed to 18 C and stirred for 50 min. On completion, the reaction mixture was quenched with ice water (40 mL). Afterwards, the organic phase was separated, washed with brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 3:1 to 1:1) to give the title compound.1H NMR (400MHz, CDCl3) delta = 8.44 – 8.40 (m, 2H), 8.28 – 8.24 (m, 2H), 1.43 (s, 9H).

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; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; SAIAH, Eddine; (264 pag.)WO2017/156181; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 116861-31-5, 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 116861-31-5 as follows.

Synthesis of compound 22: the aforementioned compound 20 (0.120 g, 0.00049 mol, 1 eq) was solubilised in DMF (3 ml). To the solution was added the aforementioned compound 21 (0.104 g, 0.00054 mol, 1.1 eq) solubilised in DMF (2 ml). The reaction mixture was stirred under reflux for 6 hours. The structure of the product was evaluated by TLC CH2Cl2 9/MeOH 1/NH4OHaq 33% 0.03. The solvent was evaporated, and the oily residue was purified by flash chromatography using a mixture of CH2Cl2 9/MeOH 1/NH4OHaq 33% 0.03 as the eluent phase. 0.084 mg of a yellow oil were obtained. Yield 42.71%. 1H NMR (400 MHz, CDCl3) delta 0.87 (d, 6H, J=6.8 Hz), 1.43 (s, 18H), 1.57-1.61 (m, 7H), 1.98-2.01 (m, 2H), 2.31-2.35 (m, 2H), 2.38-2.42 (m, 2H), 3.10-3.12 (m, 2H), 3.16-3.18 (m, 2H), 4.72 (brs, 1H, exch D2O), 5.69 (brs, 1H, D2O exch.).

According to the analysis of related databases, 116861-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Giuliani, Giammaria; Paus, Ralf; Benedusi, Anna; Marzani, Barbara; Baroni, Sergio; US2015/202132; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 112101-81-2,Some common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, 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.

Into a 4-necked 500ml round bottom flask, equipped with Dean-stark apparatus 150.0ml of toluene, 24.4gms of (R)-5-(2-aminopropyl)-2-methoxy benzene sulfonamide of the formula-IV and 12.4gms (0.1mole) of 4-fluorobenzaldehyde are charged. The reaction is effected azeotropically and the water 1.8ml (0.1mole) is separated. Then the toluene is distilled off completely under vacuum at temp max 80C. Cooled 25-35C and released the vacuum under nitrogen atmosphere – 25.0gm of thick oily compound of 2-methoxy-5-(2R)-2-{[(1-E/Z-4-fluorophenylpmethylene)amino] propyl} benzenesulfonamide of formula-IIId is obtained. Recrystallized sample (from IPA) has the following characteristics MR : 140-148C 1H NMR : (200MHz, CDCl3+DMSO-d6) delta 1.01-1.04 (d, 3H), 2.80-2.88 (t, 2H), 3.14 – 3.18 (m, 1H), 3.88 (s, 3H), 6.0, (broad, 2H), 7.12-7.57 (aromatic, 7H), 8.20 (s, imine, 1H) IR : (KBr), 3385, 3315, 2948, 1643, 1606, 1576, 1495, 1404, 1334, 1249, 1154, 1074, 1114, 518, 471cm-1

The synthetic route of 112101-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; WO2004/16582; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics