Tag: M.W=100-200

Application of 40545-33-3, These common heterocyclic compound, 40545-33-3, name is 2-Amino-5-methylbenzamide, 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 cold (0-5 C) stirred suspension of aminobenzamides 10a-c (0.016 mol) in pyridine (13 ml), 0.016 mol of the appropriate 3-phenylacryloyl chloride 11c-k was added over 30 min. After addition was complete, the solution was stirred for 24 h and then poured onto crushed ice. The precipitate was removed by filtration, washed with water, and crystallized from ethanol.

Statistics shows that 2-Amino-5-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 40545-33-3.

Reference:
Article; Raffa, Demetrio; Maggio, Benedetta; Plescia, Fabiana; Cascioferro, Stella; Plescia, Salvatore; Raimondi, Maria Valeria; Daidone, Giuseppe; Tolomeo, Manlio; Grimaudo, Stefania; Di Cristina, Antonietta; Pipitone, Rosaria Maria; Bai, Ruoli; Hamel, Ernest; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2786 – 2796;,
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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

(0243) To a stirred suspension of LiAlH4 (3.74 g, 0.09852 mol) in 200 ml anhydrous THF in a two neck RBF (1 L), was added a solution of 514 (10 g, 0.04926 mol) in 70 mL of THF slowly at 0 C. under nitrogen atmosphere. After complete addition, reaction mixture was warmed to room temperature and then heated to reflux for 4 h. Progress of the reaction was monitored by TLC. After completion of reaction (by TLC) the mixture was cooled to 0 C. and quenched with careful addition of saturated Na2SO4 solution. Reaction mixture was stirred for 4 h at room temperature and filtered off. Residue was washed well with THF. The filtrate and washings were mixed and diluted with 400 mL dioxane and 26 mL conc. HCl and stirred for 20 minutes at room temperature. The volatilities were stripped off under vacuum to furnish the hydrochloride salt of 515 as a white solid. Yield: 7.12 g 1H-NMR (DMSO, 400 MHz): delta=9.34 (broad, 2H), 5.68 (s, 2H), 3.74 (m, 1H), 2.66-2.60 (m, 2H), 2.50-2.45 (m, 5H). (0244) Synthesis of 516:

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; Alnylam Pharmaceuticals, Inc.; Novobrantseva, Tatiana; Bettencourt, Brian; Milstein, Stuart; Borodovsky, Anna; US9127275; (2015); B2;,
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. 1237535-78-2, name is 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one

To the mixture of the product of Step G (66.3 g, 0.3 mol) and 5-fluoro-3,4-dihydro- 1,8- naphthyridin-2(lH)-one (50 g, 0.3 mol) in DMF (850 mL) was added Potassium tert-butoxide (35.4 g, 0.32 mol) and the mixture was stirred at 120 C under nitrogen for 2hrs. The reaction was cooled to room temperature and filtered through a celite pad and the filtrate was removed half of the solvent. The residue was added into stirred 2L water in drops. A solid was precipitated out of the solution. The solid was filtered, washed with water and dried in air. The dried title compound (108.2 g, 98%) as a gray solid was used into next step directly. XH NMR (400 MHz, DMSO-^6) delta 10.43 (s, 1H), 7.92 (d, J= 5.8 Hz, 1H), 7.30 (d, J= 2.4 Hz, 1H), 6.98 (d, J= 8.8 Hz, 1H), 6.94 (dd, J= 8.8, 2.4 Hz, 1H), 6.21 (d, J= 5.8 Hz, 1H), 5.26 (dd, J= 5.4, 1.0 Hz, 1H), 4.08 (q, J= 7.0 Hz, 2H), 3.34 (dd, J= 5.4, 3.2 Hz, 1H), 2.89 (t, J= 7.8 Hz, 2H), 2.51 (t, J= 7.8 Hz, 2H), 1.34 (dd, J= 3.2, 1.0 Hz, 1H), 1.18 (t, J= 7.0 Hz, 3H) ppm. MS: M/e 367 (M+l)+.

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 1237535-78-2.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; ZHANG, Guoliang; WO2014/206344; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1118-69-0, name is N-Isopropylacetamide, 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 1118-69-0, Formula: C5H11NO

Preparation example 5: Preparation of (Z)-N’-(4-bromo-2,6-difluorophenyl)-N-isopropyl acetamidine 4-bromo-2,6-difluroaniline (7.87 g, 37.9 mmol)), N-isopropylacetamide (7.65 g, 75.7 mmol) and triethylamine (5.7 g, 56.9 mmol) were dissolved in toluene (150 mL), and phosphorus oxychloride (5.8 g, 37.9 mmol) was added slowly. After the addition, the mixture was heated to reflux for 3 h. Then, the reaction mixture was cooled to room temperature, the solvent was removed by reduced pressure distillation, and dichloromethane (200 mL) was added. The resultant mixture was washed with saturated sodium hydrogen carbonate solution (2×100 mL) twice, dried by anhydrous sodium sulfate, filtrated under suction, and distilled under reduced pressure, to get the solid title compound (7.3 g, yield: 66.2%).

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; Xuanzhu Pharma Co., Ltd.; WU, Frank; CHEN, Bo; (105 pag.)EP3091008; (2016); 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. 7700-07-4, name is N,N-Dimethylethenesulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C4H9NO2S

To a solution of Example 1.18.18 (69.8 mg) in N,N-dimethylformamide (6 mL) was added N,N-dimethylethenesulfonamide (118 mg), N,N-diisopropylethylamine (0.2 mL) and H20 (0.2 mL). The mixture was stirred at room temperature 4 days. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water and brine, and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was dissolved in dichloromethane and trifluoroacetic acid (10 mL, 1 :1), and the resulting solution was stirred overnight. The solvents were removed under reduced pressure. The residue was diluted with N,N-dimethylformamide (2 mL), filtered and purified by reverse-phase HPLC on a Gilson system (CI 8 column), eluting with 20-80% acetonitrile in water containing 0.1% trifluoroacetic acid, to give the title compound. NMR (400 MHz, dimethyl sulfoxide-^) delta ppm 12.82 (s, 1H), 8.53 (s, 2H), 8.00 (dd, 1H), 7.76 (d, 1H), 7.59 (dd, 1H), 7.53 – 7.37 (m, 4H), 7.37 – 7.28 (m, 2H), 7.26 (s, 1H), 6.92 (d, 1H), 4.92 (s, 2H), 3.80 (s, 2H), 3.54 (t, 2H), 3.44 – 3.34 (m, 2H), 3.30 (s, 2H), 3.11 (s, 2H), 2.98 (t, 2H), 2.77 (s, 6H), 2.07 (s, 3H), 1.39 (s, 2H), 1.27 (q, 4H), 1.11 (s, 4H), 1.06 – 0.93 (m, 2H), 0.83 (s, 7H). MS (ESI) m/e 881.2 (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; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H18N2O2

Reference Example 61Synthesis of tert-butyl methyl-[2-(2-nitrobenzenesulfonylamino) ethyl]carbamate2-Nitrobenzenesulfonyl chloride (4.9 g, 22 mmol) was added to a dichloromethane solution (100 ml) of tert-butyl (2-aminoethyl)methyl carbamate (3.5 g, 20mmol) and triethylamine (3.3ml, 24 mmol) at 0C, and stirred at room temperature overnight. Waterwas added to the reaction mixture, and extraction with dichloromethanewas performed. The organic layer was dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The residue waspurified by silica gel column chromatography (n-hexane:ethylacetate=3:2-?2:3) . The purified product was concentrated underreduced pressure to thereby obtain 5.06 g (yield: 70%) of tert-butylmethyl-[2-(2-nitrobenzenesulfonylamino)ethyl]carbamate as a yellowoil.1H-NMR (CDC13) 5ppm:1.45 (9H, s), 2.84 (3H, s), 3.26 – 3.41 (4H, m), 7.68-7.79 (2H, m),7.79-7.90 (1H, m), 8.09-8.19 (1H, m) .

According to the analysis of related databases, 121492-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2009/104819; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 1520-70-3,Some common heterocyclic compound, 1520-70-3, name is Ethanesulfonamide, molecular formula is C2H7NO2S, 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.

To a stirred solution of free acid (50 mg, 0.11 mmol) from Example 226 in 1 ML of methylene chloride was added ethyl sulfonamide (18 mg, 0.17 mmol), EDAC (25 mg, 0.13 mmol), and DAMP (2.7 mg, 0.022 mmol) sequentially.The mixture was stirred at ambient temperature for 16 h.The solvent was then removed on a rotavap under reduced pressure and the residue was purified on an Alltech sep-pak, eluding with 1percent MeOH in EtOAc to give 30 mg (50percent yield) of the title compound as a light yellow solid. 1H NMR (CDCl3, 300 MHz) delta 1.18 (d, J=6.3 Hz, 6H), 1.34 (t, J=7.5 Hz, 3H), 1.61-1.74 (m, 2H), 1.84-2.04 (m, 1H), 2.13-2.35 (m, 1H), 2.60-2.75 (m, 2H), 3.44 (p, J=7.5 Hz, 2H), 3.53-3.66 (m, 1H), 3.66-3.85 (m, 2H), 4.00-4.18 (m, 1H), 6.71 (d, J=8.7 Hz, 1H), 6.88 (d, J=15.6 Hz, 1H), 7.31 (dd, J=2.4, 8.4 Hz, 1H), 7.41 (d, J=1.8, 8.4 Hz, 1H), 7.51 (d, J=1.8 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.67 (d, J=15.6 Hz, 1H), 8.43 (s, 1H). MS (ESI+) (M+H)+ at m/z 546.

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

Reference:
Patent; Abbott Laboratories; US2004/116518; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 711007-44-2, These common heterocyclic compound, 711007-44-2, name is 2,3-Diaminobenzamide, 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.

Cbz-glycine (2.92 g, 13.89 mmol) and 120 mL of acetonitrile were added to a 250 mL reaction flask, stirred and dissolved, and CDI (2.57 g, 15.85 mmol) was slowly added, and reacted at 45 C for 1.5 hours. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), Intermediate VII (2 g, 13.23 mmol) was added and reacted at 45 C for 4 hours. TLC (dichloromethane: methanol = 10:1) monitoringAfter the raw materials are reacted, a large amount of white solid is produced, suction filtered, and dried. It was added to a 100 mL reaction flask, 50 mL of glacial acetic acid was added, and the reaction was refluxed at 120 C. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), the glacial acetic acid was concentrated under reduced pressure and dissolved in 100 mL of water.Extracted with ethyl acetate (100 mL ¡Á 2), and the organic layer was combined.Wash with saturated sodium chloride (150 mL) and dry over anhydrous sodium sulfate. Filtered off with suction, the filtrate was concentrated to give the crude product (VIII) 4.18g, yield 97.4%.

Statistics shows that 2,3-Diaminobenzamide is playing an increasingly important role. we look forward to future research findings about 711007-44-2.

Reference:
Patent; China Pharmaceutical University; Xu Yungen; Zhu Qihua; Ge Yiran; Li Hui; Zhang Guangxia; Wang Junwei; (21 pag.)CN109748923; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

156731-40-7, name is 1-(Boc-amino)-3-butene, 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. COA of Formula: C9H17NO2

Sodium hydride (583 mg of 60% dispersion in mineral oil, 14.6 mmol) was washed twice with 16 mL portions of hexane and suspended in 16 mL anhydrous THF. Reaction mixture was cooled to 0C and tert-butyl but-3-enylcarbamate (830 mg, 4.85 mmol) was added dropwise. Reaction mixture was warmed up to room temperature and stirred under argon for 30 min. Reaction mixture was cooled to 0C and freshly distilled ethyl iodide (0.78 mL, 9.7 mmol) was added dropwise. Reaction mixture was allowed to warm up to room temperature overnight, and it was then cooled to 0C and quenched with saturated ammonium chloride solution. The layers were separated and aqueous layer was extracted with Et2O. Organics were combined and washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. Crude reaction mixture was purified by flash column chromatography (hexanes:EtOAc 4:1) to give 900 mg (93%) of the title compound as a colorless oil. IR (neat) 3078, 2976, 2932, 2871, 1685 cm-1; 1H NMR (300 MHz, CDCl3): delta [ppm] 1.04-1.09 (t, 3H, J=7.1 Hz), 1.42 (s, 9H), 2.20-2.27 (m, 2H), 3.19 (br m, 4H), 4.95-5.06 (m, 2H), 5.67-5.81 (m, 1H); 13C NMR (75 MHz, CDCl3): delta [ppm] 11.58, 26.45, 31.25, 39.90, 44.32, 77.01, 114.33, 133.62, 153.36; m/z (relative intensity) 199(1), 158(5), 102(8), 57(100), 41(70), 29(52). Anal.Calcd. for C11H21NO2: C, 66.29; H, 10.62; O, 16.06. Found: C, 66.07; H, 10.66; O, 15.95.

The synthetic route of 156731-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; McMills, Mark C.; Humes, Ross J.; Pavlyuk, Oksana M.; Tetrahedron Letters; vol. 53; 7; (2012); p. 849 – 851;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6919-61-5, name is N-Methoxy-N-methylbenzamide, 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 6919-61-5, name: N-Methoxy-N-methylbenzamide

N-Methoxy-N-methyl benzamide 20 (0.1 g, 0.60 mmol) was dissolved in anhydrous diethyl ether (2.01 ml). The solution was cooled to 0 C. To this, vinyl magnesium bromide solution (0.91 ml, 1.0 M in THF) was added dropwise over 30 min at 0 C. After the completion of addition, the reaction mixture was stirred for a further 60 min at 0 C and for 30 min at room temperature. It was then quenched with 1M HCl at 0 C. The reaction mixture was diluted with diethyl ether. The organic layer was washed with brine, dried over Na2SO4,concentrated in vacuo, purified on silica gel (3:1 hexanes/EtOAc) to afford 0.04 g of 7 (55%) as a colorless oil. 1H NMR (400 MHz, CDCl3) ae 7.95 (d, J = 8.3 Hz, 2H), 7.60-7.55 (m, J = 7.4 Hz,1H), 7.49 (t, J = 8.0 Hz, 2H), 7.15 (dd, J = 10.5 Hz, 6.6 Hz, 1H), 6.40 (d, J = 17.1 Hz, 1H), 5.90(d, J = 10.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) ae 191.2, 137.5, 133.1, 132.6, 130.2, 128.8,128.7. HRMS C9H9O [M+H]+ Expected: 133.0648, Found: 133.0646.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Korwar, Sudha; Nguyen, Thuy; Ellis, Keith C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 271 – 274;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics