Tag: M.W=200-300

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. 703-12-8, name is 4-Bromo-N-methylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Bromo-N-methylbenzenesulfonamide

4-Bromo-N-methylbenzenesulfonamide (100 mg, 0.40 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (72 mg, 0.48 mmol), potassium fluoride (76 mg, 1.3 mmol), and tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.0 mL) was added. Tri-t-butylphosphine (60 muL, 0.02 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica and rinsed with ethyl acetate. The solvent was concentrated in vacuo to provide the crude product. The crude product was pre-adsorbed onto the Celite reagent and purified via Isco chromatography (the Redisep column, silica, gradient 5-50% ethyl acetate in hexane) to afford 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-methylbenzenesulfonamide (28 mg, 25%). MS (ESI) m/z 275. HPLC purity 100.0% at 210-370 nm, 9.0 min.; the Xterra RP18 column, 3.5mu, 150*4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

The synthetic route of 703-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2008/221201; (2008); A1;,
Amide – Wikipedia,
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Related Products of 6292-59-7, 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 6292-59-7 as follows.

c) A solution of 0.353 g of 4,6-dichloro-5-(2-methoxyphenoxy)-2-(thiophen-2-yl)-pyrimidine in 5 ml of DMSO was heated to 150° C. with 0.376 g of p-tert-butylbenzenesulphonamide for 30 minutes. The solution was concentrated in a high vacuum and the oily residue was poured on to ice, made acid (pH=3) and the suspension was extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel with toluene-ethyl acetate 9:1 and yielded 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(thiophen-2-yl)-pyrimidin-4-yl]-benzenesulphonamide as a white foam.

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US5292740; (1994); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 112434-18-1, 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. 112434-18-1, name is Benzyl (2,4-difluorophenyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

Step 2-Preparation of (2,4-difluoro-3-formyl-phenyl)-carbamic acid benzyl ester (53)Into a round bottom flask was added (2,4-difluoro-phenyl)-carbamic acid benzyl ester (52, 3.83 g, 14.5 mmol) in tetrahydrofuran (148 ml, 1.82 mol). The solution was chilled to 78 C. and n-butyllithium (1.60 M in hexane, 19.1 mL, 30.0 mmol) was added over 30 minutes followed by the addition of, N,N-dimethylformamide (1.12 mL, 14.5 mol). The reaction mixture was allowed to warm to ambient temperature and was stirred overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and crystallized from ether to give compound 53 (3.0 g, 71%).

The chemical industry reduces the impact on the environment during synthesis Benzyl (2,4-difluorophenyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Spevak, Wayne; Cho, Hanna; Ibrahim, Prabha N.; Shi, Shenghua; Mamo, Shumeye; Gillette, Samuel J.; Zhu, Hongyao; US2008/167338; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 83922-51-4, name is N-(3-Bromophenyl)methanesulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C7H8BrNO2S

A solution of N-(3-bromophenyl)methanesulfonamide (0.500 g, 1.999 mmol), sodium hydride (60.00 %, 0.096 g, 2.399 mmol) and methyl 4-(bromomethyl)-3-fluorobenzoate (0.543 g, 2.199 mmol) in N,N-dimethylformide (10 mL) was stirred at the room temperature for 5 hr. Then, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated ammonium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; ethyl acetate / hexane = 0 % to 30 %) to give methyl4-((N-(3-bromophenyl)methylsulfonamido)methyl)-3-fluorobenzoate as yellow solid (0.490 g, 58.9 %).

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; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
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Amide – an overview | ScienceDirect Topics

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. 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 24036-52-0

A degassed suspension of commercially available 6-Bromo-4H- benzo[l ,4]oxazin-3-one (8.39 g), Zn(CN)2 (3.46 g) and Pd(PPh3)4 (2.13 g) in DMF (70 mL) was stirred in a oil bath (80C) overnight. The mixture was cooled to room temperature and then poured into water (500 mL). The precipitate was collected by suction, air dried, washed with pentane, dissolved in CH2Cl2ZMeOH (1 : 1), filtered through an silica pad and concentrated to yield a yellow solid (5.68 g, 89%). [MH]+ = 175.

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; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63667; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H20N2O2

A mixture of 2-(4-fluoropiperidin-l-yl)acetic acid(239 mg, 1.48 mmol), HATU (619 mg, l.63mmol) and DIPEA (524 mg, 4.44 mmol) in DCM (10 mL) and DMF(lOmL) was stirred at room temperature for 0.5 h. Then tert- butyl 4-aminophenethylcarbamate (350 mg, 1.48 mmol) was added and the reaction was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as yellow solid (400 mg, 71.3% yield). ‘H NMR (500 MHz, DMSO- d6) d: 10.38 (s, 1H), 7.50 (d, J= 8.3 Hz, 2H), 7.18 (t, J= 8.5 Hz, 2H), 6.87 (d, J= 5.5 Hz, 1H), (0881) 4.92 (d, J= 52.6 Hz, 1H), 3.95 (dd, J= 34.1, 9.3 Hz, 1H), 3.11 (dd, J= 13.9, 6.5 Hz, 5H), 2.81 (d, .7= 79.7 Hz, 1H), 2.65 (t, J= 7.4 Hz, 2H), 2.20 – 1.99 (m, 4H), 1.91 (s, 1H), 1.36 (s, 10H).

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 94838-59-2.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1151665-15-4, 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. 1151665-15-4, name is tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 3-(2-chloro-7, 8-dihydro- 1, 6-naphthyridin- 6(5H)-yl)-2-methylpropanoate was prepared starting from tert-butyl 2-chloro- 7,8- dihydro- 1,6- naphthyridine- 6(5H) – carboxylate in accordance with scheme 6. Tert-butyl 2-chloro-7,8-dihydro-1,6- naphthyridine-6(5H)-carboxylate (3.22 g; 12 mmol; 1 eq) was dissolved in DCM (100 mL). TFA (13.7 g; 120 mmol; 10 eq) was added under stirring at RT. Themixture was stirred for 20h at RT. 50 mL of a saturated NaHCO3 solution was added followed by the addition of solid NaHCO3 while stirring until the pH of the aqueous phase was 7. After phase separation, the organic phase was dried with MgSO4 and evaporated. The aqueous phase was saturated with NaC1 under stirring foliowed by addition of 200 mL DCM and stirring for 30 mm. After phaseseparation, the organic phase was dried with MgSO4 and evaporated. The yield of the combined product 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine was 2.01 g (11.92 mmol; 99%).

The synthetic route of tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; LANGE, Udo; OCHSE, Michael; VAN DER KAM, Elizabeth; VAN BERGEIJK, Jeroen; TURNER, Sean; OELLIEN, Frank; WALLESER, Patrick; AMBERG, Wilhelm; HORNBERGER, Wilfried; GENESTE, Herve; MEZLER, Mario; HUTCHINS, Charles; (301 pag.)WO2017/36978; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, 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 85006-25-3, Recommanded Product: 85006-25-3

Commercially available Compound 12 (6.7 g, 28.7 mmol), 2-methoxyethanol (2.267 mL, 28.7 mmol) and triphenylphosphine(9 g, 34.5 mmol) were dissolved in tetrahydrofuran (67 mL) under water-cooling bath, and 2.2 mol/L DEADtoluenesolution (15.67 mL, 34.5 mmol) was added dropwise to the solution over 30 minutes. Then, the reaction mixturewas stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silicagel column chromatography (hexane-ethyl acetate) to give Compound 13 (8.15 g, Yield 97.4%).LC/MS (Method 2) RT = 2.20, MS (m/z) = 292

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; Shionogi & Co., Ltd.; YUKIMASA, Akira; NAKAMURA, Kenichiroh; INAGAKI, Masanao; KANO, Kazuya; FUJIU, Motohiro; YAMAGUCHI, Hiroki; HATA, Kayoko; INOUE, Takatsugu; (253 pag.)EP3330256; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 143557-91-9,Some common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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.

3alpha-Cyclopropylmethoxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester A reaction flask was charged with crude 3alpha-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester (5.5 g) in dry DMF (25 mL) under Argon. NaH (60% in oil, 0.968 g, 24.2 mmol) was added in portions and the mixture was stirred at 50 for 1 h. The mixture was cooled to rt and bromomethylcyclopropane (3.252 g, 24.2 mmol) was added followed by stirring at rt for 20 h under Argon. The reaction mixture was quenched with water and the product extracted into EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (3.354 g). 1H NMR (CDCl3) delta 3.98-3.94 (m, 2H), 3.44-3.40 (m, 1H), 3.05 (d, 2H), 1.96-1.88 (m, 2H), 1.79-1.62 (m, 6H), 1.29 (s, 9H), 0.88-0.79 (m, 1H), 0.35-0.30 (m, 2H), 0.04-0.00 (m, 2H); 13C NMR (CDCl3) delta 153.4, 78.9, 73.0, 72.5, 52.7, 34.9, 28.5, 28.1, 10.9, 2.8.

The synthetic route of 143557-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACADIA PHARMACEUTICALS, INC.; Skjaerbaek, Niels; Koch, Kristian Norup; Friberg, Bo Lennart Mikael; Tolf, Bo-Ragnar; (70 pag.)US9522906; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 749927-69-3, 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 749927-69-3 as follows.

A 200 liter reactor was charged with 4-bromo-2-fluoro-N-methylbenzamide (12.0 kg, 51.7 mole)1-Aminocyclobutane carboxylic acid(6.3 kg, 61.7 mole),Potassium carbonate (16.5 kg, 155 mole),2-acetylcyclohexanone (0.12 kg, 1.05 mole),1.2 liters of water, dissolved in 70 liters of DMF, under stirring with stirring CuI (0.2kg, 1.05mol)Heated to 110 degrees, the reaction 24 hours. After the reaction was completed, add water cooling 120 liters,Then add ethyl acetate extraction.The aqueous phase was retained, adjusted to pH = 1 with 1 N hydrochloric acid and the precipitated solid was filtered. Beating with water,Get pure 11.8 kg, product 86%.

According to the analysis of related databases, 749927-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Xipu Pharmaceutical Technology Co., Ltd.; Lianyungang Shengfeng Chemical Co., Ltd.; Qin Yong; Chen Yue; Bian Junjie; Yu Jianhua; Wang Mingfa; Dai Xiaoming; (6 pag.)CN107501237; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics