Month: August 2021

Application of 98-18-0, 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. 98-18-0, name is 3-Aminobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-aminobenzenesulfonamide (413.3 mg, 2.40 mmol), 2,5- difluoro-4-methyl-benzoic acid (344.3 mg, 2.0 mmol), HATU (684.4 mg, 1.80 mmol) and N- methylmorpholine (439.8 mu, 4.0 mmol) in DMF (2 mL) was stirred at 40 °C for 2 hours. The reaction was poured into IN HCl and extracted with ethyl acetate (3x). The organics were combined, washed with water, brine, dried with Na2S04 and evaporated to dryness to give 2,5-difluoro-4-methyl-N-(3-sulfamoylphenyl)benzamide (610 mg, 94percent) as a solid that was used in the next step without further purification. ESI-MS m/z calc. 326.05, found 327.3 (M+1) +; Retention time: 1.25 minutes (3 minutes run).

The synthetic route of 3-Aminobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); A1;,
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3144-09-0, name is Methylsulfonamide, 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. Quality Control of Methylsulfonamide

A mixture of 4-bromobenzaldehyde (0.250 g, 1.40 mmol), methanesulfonamide (0.154 g, 1.62 mmol), copper iodide (0.0510 g, 0.270 mmol), N,N-dimethylglycine (0.0280 g, 0.270 mmol), and potassium phosphate tribasic (0.716 g, 3.38 mmol) in DMF (5.00 mL) was stirred at reflux for 16 hours. The mixture was diluted with EtOAc (50 mL), washed with water (50 mL), and then saturated aqueous LiCl (5 mL). The combined aqueous layers were then back-extracted with EtOAc (50 mL). The organic layers were combined, washed with brine (50 mL), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure, to provide N-(4-formylphenyl)methanesulfonamide (0.161 g, 58%) as a yellow oil

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 340187-12-4, These common heterocyclic compound, 340187-12-4, name is (9H-Fluoren-9-yl)methyl (2-bromoethyl)carbamate, 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.

A mixture of Example 123 (21 mg, 0.05 mmol), (9H-fluoren-9-yl)methyl2- bromoethylcarbamate (36 mg, 0.1 mmol) and K2CO3 (20 mg, 0.15 mmol) in DMF (1 mL) was stirred stirred at rt overnight. Piperidine (0.5 mL) was added and the mixture was stirred for another hour. The reaction mixture was purified by etaPLC to afford the product as a white solid. 1H-NMR (400 MHz, CD3CN) delta = 7.97 (br s, 2H), 7.04 (d, J = 8.1 Hz, IH), 6.76 (dd, J = 2.8, 8.4 Hz, IH), 6.72 (d, J = 2.4 Hz, IH), 4.75 (t, J = 5.6 Hz, 2H), 4.31 (s, 2H), 4.02 (m, 2H), 3.95 (t, J = 6.4 Hz, 2H), 3.49 (t, J = 5.6 Hz, 2H), 3.45 (t, 7 = 6.0 Hz, 2H), 2.93-2.86 (m, 4H), 2.80 (s, 3H), 1.80-1.76 (m, 4H), 1.53 (m, IH), 1.43- 1.38 (m, 2H), 1.24 (ddd, J = 4.0, 12.4, 24.2 Hz, 2H); MS calcd. for [M+H]+ C2iH34N7O3S: 464.2; found: 464.2.

The synthetic route of 340187-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/97428; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 148017-28-1, A common heterocyclic compound, 148017-28-1, name is tert-Butyl sulfamoylcarbamate, molecular formula is C5H12N2O4S, 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.

b) Preparation of a sulfamide compound To a solution of (2R,4S)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (i.e., a substrate) in tetrahydrofuran (THF), triphenylphosphine (PPh3), N-t-butoxycarbonylsulfamide (BSMD), and azodicarboxylic acid diethyl ester (DEAD) are successively added under ice cooling. The conditions for this reaction are shown in Table 2, Step A-6. The reaction mixture is diluted with toluene, concentrated, diluted with toluene, and the formed crystals are filtered off. The filtrate is concentrated. The residue is purified by silica gel column chromatography to give (2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine. NMR delta(CDCl3) ppm: 1.41(s, 9H), 1.55(s, 9H), 1.19 to 2.0(m, 2H), 2.35(s, 3H), 3.32(dd, J=11.4 Hz, J=8.2 Hz, 1H), 3.6 to 3.9(m, 3H), 3.9 to 4.1(m, 1H), 4.5(m, 1H), 6.15(s, 2H). IR nu (KBr) cm-1: 3420, 3320, 1706, 1686, 1666.

The synthetic route of 148017-28-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi Seiyaku Kabushiki Kaisha; US5317016; (1994); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18469-37-9, name is 4-Bromo-N,N-dimethylbenzamide, 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 18469-37-9, SDS of cas: 18469-37-9

N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0243) To a solution of 4-bromo-N,N-dimethylbenzamide (11.0 g, 48.23 mmol) in dioxane (300 mL) were added 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (14.7 g, 57.89 mmol), Pd(dppf)Cl2 (3.5 g, 4.78 mmol) and potassium acetate (14.2 g, 144.69 mmol) at room temperature. The resulting mixture was stirred for 16 h at 100 C. The reaction mixture was cooled to room temperature and the resulting solid was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 40% gradient) to yield N,N-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as orange solid (10.0 g, 70%). MS: m/z=276.0 [M+H]+.

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

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); 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. 579-10-2, name is N-Methylacetanilide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

A solution of N-methyl-N-phenylacetamide (73.8 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 5 C. and the resulting solution was allowed to warm to rt and was maintained 16 h. The reaction mixture was diluted with iced water (100 mL) and was extracted with dichloromethane (2×50 mL). The combined organic layers were dried (sodium sulfate) and concentrated. The residue was purified by Flash chromatography (10/1 ethyl acetate/petroleum ether) to give 4-(N-methylacetamido)benzene-1-sulfonyl chloride in 11% yield as a white solid. 1H NMR (CDCl3) delta 8.09 (d, 2H), 7.48 (d, 2H), 3.38 (s, 3H), 2.17 (s, 3H).

According to the analysis of related databases, 579-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Memory Pharmaceuticals Corporation; US2010/29629; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16066-84-5, 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. 16066-84-5, name is tert-Butyl methylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00519] Step C: A microwave reaction tube equipped with a stir bar was charged with 6-(((1s,4s)-4-(6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridin-1-yl)cyclohexyl)oxy)-2-methylpyridazin-3(2H)-one (0.029 g, 0.066 mmol), tert-butyl methylcarbamate (0.035 g, 0.26 mmol), dioxane (0.5 mL), dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphane (0.012 g, 0.026 mmol), sodium t-butoxide (0.013 g, 0.13 mmol) and Pd2dba3 (0.012 g, 0.013 mmol) under a nitrogen atmosphere. The tube was sealed and warmed to 100 C overnight, partitioned between water/EtOAc, extracted with EtOAc, dried over sodium sulfate and concentrated. The crude material was taken forward without further purification.

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, tert-Butyl methylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); 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. 114790-39-5, name is Benzyl (2,2-dimethoxyethyl)carbamate, A new synthetic method of this compound is introduced below., Application In Synthesis of Benzyl (2,2-dimethoxyethyl)carbamate

To a solution of benzyl N-(2,2-dimethoxyethyl)carbamate (1700 g, 7.10 mol), KOH (1755 g, 31.28 mol) and benzyltriethylammonium chloride (32.37g, 142.1 mmol) in toluene (7.82 L) was added 3-bromoprop-1-ene (1117.4 g, 9.24 mol) dropwise with stirring at room temperature. The resulting solution was stirred for 24 h at room temperature. Two batches were thus run in parallel. The reaction was then quenched by the addition of 10 L of water. The resulting solution was extracted with 2×7 L of toluene and the organic layers combined. The organic phase was washed with 2×10 L of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to afford benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en- 1 -yl)carbamate as pale yellow oil.

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; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1943-79-9, name is Phenyl methylcarbamate, 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. Recommanded Product: Phenyl methylcarbamate

To a solution of amine 11 (0.8 g, 3.35 mmol) in 20 mL of DMSO,were added N-methylphenylcarbamate (0.76 g, 5.03 mmol) andtriethylamine (0.7 mL, 5.03 mmol). The mixture was stirred andheated at 60 C for 3 h, then hydrolyzed and extracted with CH2Cl2.The organic layer was washed with an aqueous solution of 1 M HCland water, dried over MgSO4, filtered and concentrated underreduced pressure. The obtained product was then purified by flashchromatography using a mixture of cyclohexane/ethyl acetate(8:2). Recrystallization from toluene gave 11f as a white solid (45%yield); Mp 142-144 C; 1H NMR (300 MHz, CDCl3): delta 7.98 (d, 1H,8.7 Hz), 7.62 (dd, 1H, 7.8 Hz and 1.2 Hz), 7.51 (dd, 1H, 7.8 Hz and1.2 Hz), 7.32 (t, 1H, 7.8 Hz), 6.92 (d, 1H, 8.7 Hz), 4.80 (br s, 1H), 4.23(br s, 1H), 4.09 (s, 3H), 3.60 (q, 2H, 6.6 Hz), 3.38 (t, 2H, 6.6 Hz), 2.67(d, 3H, 4.8 Hz); 13C NMR (75 MHz, CDCl3): delta 161.7,159.1,145.0,139.3,136.1, 130.2, 126.3, 125.1, 123.9, 112.7, 53.4, 41.6, 32.0, 27.1; IR (upsilon,cm-1, KBr): 3368 (NH), 3291 (NH), 1653 (C=O); MS (APCI, pos. 30V) m/z: [M+H]+, 260.30. HRMS (ESI+): m/z = calcd. for C14H17N3O2[M+H]+ 260.13935 found: 260.13831.

The synthetic route of 1943-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Landagaray, Elodie; Ettaoussi, Mohamed; Rami, Marouan; Boutin, Jean A.; Caignard, Daniel-Henri; Delagrange, Philippe; Melnyk, Patricia; Berthelot, Pascal; Yous, Said; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 621 – 631;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 3823-19-6, 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. 3823-19-6, name is 2-Bromo-N-(4-(trifluoromethyl)phenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Potassium tert-butoxide (65.2 mg, 0.581 mmol, 1.05 eq) wasadded to a solution of thiols 10a~ b (0.554 mmol, 1.00 eq) in 5mLanhydrous N,N-dimethylformamide. The mixture was stirred atroom temperature before the a-bromoacetamide (0.554 mmol,1.00eq) was added, then the mixture was stirred for another 2 h. Toafford desired thioethers 11a~ e and 11h ~ l, the resulting mixturewas diluted with 50 mL ethyl acetate, washed with water(50 mL 3), dried with anhydrous sodium sulfate, and concentratedin vacuum. The residue was purified with a silica gel chromatographycolumn as white or pale yellow solid of 41e63% yield.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-N-(4-(trifluoromethyl)phenyl)acetamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Han, Sheng; Sang, Yali; Wu, Yan; Tao, Yuan; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen, Fen-Er; European Journal of Medicinal Chemistry; vol. 185; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics