Month: August 2021

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. 960234-99-5, name is 3-Amino-5-methoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Amino-5-methoxybenzamide

General procedure: 3-aminobenzamide (50 mg, 0.37 mmol) and maleic anhydride (43.2 mg, 0.44 mmol) were dissolved in dry THF (1 ml) and stirred at room temperature for 18 hours. The precipitate was filtered off and dried in vacuo to give 2 (71 mg, 83%).

The synthetic route of 960234-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ekblad, Torun; Lindgren, Anders E.G.; Andersson, C. David; Caraballo, Remi; Thorsell, Ann-Gerd; Karlberg, Tobias; Spjut, Sara; Linusson, Anna; Schueler, Herwig; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 546 – 551;,
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Reference of 1882-71-9,Some common heterocyclic compound, 1882-71-9, name is 2-Amino-5-methoxybenzamide, molecular formula is C8H10N2O2, 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: A mixture of 2-aminobenzamide (1, 4.0 mmol), carboxamide (2, 6.0 mmol), Yb(OTf)3 (0.20 mmol,5.0 molpercent), and mesitylene (5.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 120-165 oC (bath temp.) for 6 h with stirring. Then, the reaction mixture was cooled to room temperature, and analyzed by GLC, GC-MS (EI), and LC-MS (ESI). After evaporation of mesitylene under vacuum,the products (3) were isolated by recrystallization from MeOH/hexane and/or medium pressure column chromatography on silica gel (eluent: EtOAc/hexane = 50/50 ~ EtOAc 100percent. For 3j, eluent:MeOH/CHCl3 = 50/50). 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6. The analytical and spectral data of 3a-e,38 3f,39 3g,40 3h,41 and3j,42 were consistent with those reported previously. The product, 3i, was characterized below.

The synthetic route of 1882-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yoshimura, Tsutomu; Yuanjun, Di; Kimura, Yu; Yamada, Hisatsugu; Toshimitsu, Akio; Kondo, Teruyuki; Heterocycles; vol. 90; 2; (2015); p. 857 – 865;,
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. 78888-18-3, name is tert-Butyl allylcarbamate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl allylcarbamate

Tert-butyl N-(2-oxiranylmethyl)carbamate was synthesized according to the method of Rocheblave (30). 1 g (6 mmol, 1 equiv) of N-t-BOC protected 3 was dissolved in 50 mL dry CH2Cl2. The solution was brought to 0 C. and kept cold upon addition or 2.8 g (12 mmol, 2 equiv) MCPBA. The solution was then brought to room temperature and stirred overnight.About half of the reaction mixture was taken and diluted with additional 80 mL of CH2Cl2. The solution was washed with 10% Na2SO3, followed by washing with saturated NaHCO3 3 times, and finally by washing with water. The organic layer was dried over Na2SO4 and concentrated in vacuo, yielding crude epoxide 4. By 1H NMR, approximately 85% yield was achieved.1H NMR (400 MHz, CDCl3): delta 1.44 (s, 9H), 2.59-2.78 (brm, 2H), 3.04-3.54 (m, 3H), 4.75 (brs, 1H).

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; University of Southern California; US2008/312440; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 78191-00-1, name is N-Methoxy-N-methylacetamide, 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. name: N-Methoxy-N-methylacetamide

4-Prop-2-ynyl-morpholine (22 g, 176 mmol) was dissolved under nitrogen in THF (40 mL) and cooled to-40 C. Then a 2 M solution of isopropyl magnesium chloride in THF (97 mL, 193 mmol) was added while keeping the temperature below-20 C. Stirring at – 40 C to-30 C was continued for 30 min. In a separate flask, N-methoxy-N- methylacetamide (20 g, 193 mmol) was dissolved under nitrogen in THF (40 mL) and cooled to-10 C in ice/MeOH. The Grignard solution prepared above was transferred to the Weinreb amide solution at-10 C via teflon tubing under slightly positive nitrogen pressure in vessel 1. There was no exotherm. Stirring at-10 C to 0 C was continued for 2 h. Ther resulting white suspension was poured on a 1 : 1-mixture of ice and saturated NH4Cl solution (400 mL). Extraction: 2 x AcOEt, 1 x saturated NaCl solution. One obtained a yellow oil (26. 1 g, 89 %). Chromatography on silica gel in heptane/ethyl acetate 1: 2 gave 19.4 g (66 %) of a brown oil which was distilled in the Kugelrohr at 130 C/0. 2 mbar. One obtained 15.8 g (53 %) of a yellow oil.

The synthetic route of N-Methoxy-N-methylacetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/94828; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1000698-88-3, name is tert-Butyl (2-amino-4,5-difluorophenyl)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 1000698-88-3, Quality Control of tert-Butyl (2-amino-4,5-difluorophenyl)carbamate

e) N-Benzyl-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-l-yll-2-cyclopentyl- acetamide; To a solution of 5.0 g (20.47 mmol) (2-amino-4,5-difluoro-phenyl)-carbamic acid tert- butyl ester (Example 73, intermediate g) in 50 ml methanol, 2.21 g (22.57 mmol) cyclopentanecarbaldehyde (commercially available) were added. After stirring for 5 min. at room temperature, 3.2 g (20.5 mmol) p-chlorobenzoic acid and 2.5 ml (20.47 mmol) benzyl isocyanide (commercially available) were added. After stirring for 19 h, 38.38 ml (153.52 mmol) 4 M hydrochloric acid in dioxane were added dropwise over 5 min. After 5 h the solution was poured on 500 ml saturated aqueous sodium bicarbonate solution and the phases were separated. The organic layer was extracted three times with ethyl acetate and the combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n- heptane : ethyl acetate (100 : 0 to 50 : 50). Light yellow foam (97%). MS (Turbo Spray): m/z = 480.1 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-amino-4,5-difluorophenyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BENSON, Gregory Martin; BLEICHER, Konrad; FENG, Song; GRETHER, Uwe; KUHN, Bernd; MARTIN, Rainer E.; PLANCHER, Jean-Marc; RICHTER, Hans; TAYLOR, Sven; WO2010/28981; (2010); A1;,
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Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 518057-72-2, name is 5-Amino-2-fluorobenzamide, 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. category: amides-buliding-blocks

To a solution of 5-amino-2-fluoro-benzamide (0.88 g, 5.7 mmol) and DIEA (3.0 mL, 17 mmol) in THF (20 mL) and dichloromethane (10 mL) at 0 C was added a solution of 6-cyclopropyl-4- [2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-3-carbonyl chloride (2.1 g, 5.4 mmol) in dichloromethane. The reaction mixture was removed from the ice bath and stirred at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was concentrated in vacuo and the resulting solid was purified using silica gel chromatography (0-60% ethyl acetate/hexanes) to provide N-(3 -carbamoyl -4-fluoro-phenyl)-6- cyclopropyl-4-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-3-carboxamide (1.1 g, 40%). ESI-MS m/z calc. 505.13, found 506.2 (M+l)+; retention time (Method B): 1.4 minutes (3 minute run). ‘H NMR (400 MHz, DMSO-d6) delta 10.41 (s, 1H), 8.55 (s, 1H), 7.99 (dd, J = 6.5, 2.8 Hz, 1H), 7.87 – 7.76 (m, 1H), 7.69 (d, J = 14.5 Hz, 2H), 7.45 (d, J = 8.8 Hz, 1H), 7.32 – 7.18 (m, 2H), 7.07 (ddd, J = 8.8, 2.8, 1.3 Hz, 1H), 6.59 (s, 1H), 3.80 (s, 3H), 2.07 (p, J = 6.7 Hz, 1H), 0.99 – 0.87 (m, 4H) ppm.

The synthetic route of 5-Amino-2-fluorobenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); 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 72179-84-1 as follows. Quality Control of (Methylsulfamoyl)amine

Material from Example 73-Step 1 (40 mg, 0.098 mmol) was dissolved in tetrahydrofuran (5 mL) and 1,1?-carbonyldiimidazole (47.5 mg, 0.293 mmol) was added. The mixture was heated to 60 C for 1 hour, then 1,8-diazabicyclo[5.4.0]undec-7-ene (44.6 mg, 0.293 mmol) and Nmethylsulfuric diamide (32.3 mg, 0.293 mmol) were added followed by stirring at room temperature for 12 hours. The mixture was concentrated, and the residue was dissolved in CH3OH (1.3 mL) to which a couple of drops of acetic acid were added to adjust the pH to 6-7. The filtered solution was purified by preparative HPLC (0.1% CF3CO2H/H20/CH3CN) to give the titled compound (28 mg, 0.056 mmol, 57.1% yield). ?H NMR (400 MHz, DMSO-d6) ppm 11.25 (s, 1H), 7.42 -7.36 (m, 1H),7.33 – 7.08 (m, 4H), 7.06 – 6.96 (m, 2H), 6.86 (d, J = 7.6 Hz, 2H), 3.73 (s, 2H), 3.26 – 3.16 (m, 3H),2.46 (s, 2H), 2.32 – 2.20 (m, 2H), 2.09 (t, J = 7.2 Hz, 1H), 1.73 (s, OH), 1.43 (s, 2H), 1.34 (s, 1H), 1.30- 1.21 (m, 1H), 1.18 (s, 1H), 1.13 (s, 1H), 1.07 (s, 1H), 0.93 (s, 1H).

According to the analysis of related databases, 72179-84-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; BLACK, Lawrence, A.; BUNNELLE, William, H.; CHEN, Da; CLAPHAM, Bruce; DEGOEY, David, A.; DENG, Xiangjun; FU, Liqiang; HAZELWOOD, Lisa, A.; KONG, Linglong; LANG, Qingyu; LEE, Chih-Hung; LI, Mingfeng; LUNDGAARD, Greta, L.; PATEL, Meena, V.; TAO, Ruihong; ZHANG, Lin; ZHANG, Qingwei; ZHENG, Qiangang; ZHU, Wei; (289 pag.)WO2017/177004; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

Step 1: 4-bromo-1-chloro-2-fluorobenzene (64 kg) and dry toluene (170 kg) were charged to the 2000 L steel reaction vessel under nitrogen. The reactor was evacuated and backfilled with N2 for three times, and cooled to between -10 and 5° C. under nitrogen atmosphere. To the solution was added dropwise i-PrMgCl.LiCl (280 kg, 1.3M in THF) at between -10 and 10° C. The reaction was stirred for a further 15 to 30 min at between -10 and 10° C. and then warmed to about 20 to 25° C. over 1 h. The reaction mixture was stirred for another 6 h stir to complete the exchange. The resulting solution was cooled to between -50 and -40° C. A solution of 2-chloro-N-methoxy-N-methylacetamide (44.5 kg) in dry toluene (289 kg) was added dropwise to the above solution at while maintaining the temperature between -50 and -30° C. The reaction mixture was warmed to between 20 and 25° C. over 1 h and then stirred for 3 h to complete the reaction. The reaction was quenched by addition of 1N aq. HCl (8081 g) at a temperature between -5 and 15° C. The aqueous layer was separated and organic layer was filtered through a pad of diatomaceous earth. The organic layer was washed with 10percent aq. NaCl solution (320 kg) twice, then concentrated to about 300 L to obtain 1-(4-chloro-3-fluorophenyl)-2-chloroethanone (51.8 kg, 81.9percent yield) as product in toluene.

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; Genentech, Inc.; Lin, Jinguang; Chestakova, Alexandra; Gu, Wei; Iding, Hans; Li, Jing; Linghu, Xin; Meier, Patrik; Sha, Chunbo; Stults, Jeffrey; Wang, Youchu; Zhang, Haiming; Zhang, Jianqian; Zhang, Tao; (56 pag.)US2017/22183; (2017); A1;,
Amide – Wikipedia,
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Application of 6312-87-4, These common heterocyclic compound, 6312-87-4, name is N-(4-Phenoxyphenyl)acetamide, 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: Dimethylformamide (3 mmol) was added to N-phenylacetamides(2a-2g, 1 mmol) in an ice bath, then phosphoryl chloride(15 mmol) was added dropwise to the mixture and was stirredat ice bath for 20 min, then the reaction proceeded at temperature80e90 C for 7e10 h. After completion of the reaction, ice is addedto the mixture and was stirred, then the formed precipitate wasfiltrated and recrystallized in ethanol [31]. Compounds 3a, 3c, 3d, 3f and 6a were reported in the literatures[32e35].2.3.1. 2-Chloro-6-phenoxyquinoline-3-carbaldehyde (3b)Yellow solid; yield: 61%; mp: 110e113 C; 1H NMR (300 MHz-CDCl3) d 7.18e7.20 (d, 2H, J 6 Hz, AreH), 7.26e7.30 (t, 1H, J 6 Hz,AreH), 7.47e7.53 (m, 2H, AreH), 7.75e7.79 (m, 2H, AreH),8.08e8.11 (d, 1H, J 9 Hz, AreH), 8.92 (s, 1H, AreH), 10.37 (s, 1H,CHO).

The synthetic route of 6312-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirzaei, Salimeh; Hadizadeh, Farzin; Eisvand, Farhad; Mosaffa, Fatemeh; Ghodsi, Razieh; Journal of Molecular Structure; vol. 1202; (2020);,
Amide – Wikipedia,
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