Tag: M.W=200-300

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. 16313-66-9, name is 2-Amino-5-bromobenzamide, A new synthetic method of this compound is introduced below., Safety of 2-Amino-5-bromobenzamide

General procedure: To a solution of 2-aminobenzamide 1 (0.24 mmol, 1 equiv) and 2-alkynylbenzaldehyde 2 (0.24 mmol, 1 equiv) in DMSO (4 mL) was added AgNO3 (8 mg, 20 mol%). The resulting mixture was then heated at 120 C for 4 h. After completion of the reaction, the mixture was extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4), and evaporated. The crude product was purified by chromatography (silica gel, acetone/hexane 20:80) to afford the product.

The synthetic route of 16313-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sonawane, Amol D.; Shaikh, Yunnus B.; Garud, Dinesh R.; Koketsu, Mamoru; Synthesis; vol. 51; 2; (2019); p. 500 – 507;,
Amide – Wikipedia,
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Related Products of 109903-35-7, 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. 109903-35-7 name is 4-Amino-N-methylbenzenemethanesulfonamide, 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.

Example 23: 1-(4-{[5-acetyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)- ylidene]amino}phenyl)-lambda/-methylmethanesulfonamide hydrochloride; A mixture of 4-amino-N-methyl-alpha-toluenesulphonamide (200mg, I .Ommol), ethyl isothiocycanate (104mg, 1.20mmol, 0.1 ml) and triethylamine (0.2ml) in ethanol (5ml) was stirred at reflux for 2 hours. The solvent was then removed by rotary evaporation, the resulting material was then suspended in toluene (5ml) and treated with 3-chloro-2,4- pentanedione (0.14g, 1.05mmol, 0.13ml) and the whole mix stirred at 9O0C (oil bath temperature) for 3 hours, and allowed to cool. The reaction mix was filtered and the filtrate evaporated under reduced pressure to give a yellow oil, which was purified by MDAP (mass directed auto-preparation). The relevant fractions were combined and the solvent removed by rotary evaporation to give a brown oil, which was dissolved in dichloromethane (1 ml) and treated with 1 M ethereal HCI (1 ml). The solvent was removed by air drying. The product was triturated in ether, the liquid was decanted off and the residual material was vacuum oven dried to give the title compound as a beige coloured solid (98mg, 24%).LC/MS (ES): Found 368 (ES+), retention time 2.35mins. Ci6H2IN3O3S2 requires 367. 1 H-NMR (400MHz, MeOD-d4): delta 1.49 (3H, t, J=7Hz), 2.52 (3H, s), 2.71 (3H, s), 2.76 (3H, s), 4.31 (2H, m), 4.42 (2H, s), 7.55 (2H, m), 7.66 (2H, d, J=8Hz).

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53448; (2009); 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. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H14FNO2

To a solution of 4-fluorophenylcarbamic acid te/t-butyl ester (1.3 g, 6.2 mmol) in anhydrous tetrahydrofuran (15 mL) was added sodium hydride (60% dispersion in mineral oil, 261 mg, 6.8 mmol). After the initial gas evolution had ceased, the reaction was allowed to stir for 15 minutes. Tetra-n-butylammonium iodide (227 mg, 0.6 mmol) was then added followed by addition of the 2-chloro-5-chloromethyl thiazole prepared above. The mixture was heated to reflux for 1 hour. After cooling, the reaction was carefully neutralized with cold saturated sodium bicarbonate (10 mL) and extracted with ethyl acetate (2 x 20 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a dark oil. Flash chromatography (silica gel; 5%- 10% ethyl acetate in hexanes) provided 2-chloro-thiazol-5-ylmethyl-4- fluorophenylcarbamic acid te/t-butyl ester (1.5 g, 4.4 mmol) as a yellow oil.

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 60144-53-8.

Reference:
Patent; WYETH; WO2008/73929; (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. 698-67-9, name is 4-Bromobenzamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6BrNO

The under nitrogen atmosphere, 4-bromobenzamide (597 mg, 3 mmol, 1.0 eq.) was dissolved in 25 ml of triethylamine, and then added trimethylsilylacetylene (2.94 g, 30 mmol, 10 eq), bis(triphenylphosphine) palladium dichloride (421 mg, 0.6 mmol, 0.2 eq.), cuprous iodide (228 mg, 1.2 mmol, 0.4 eq.). The reaction mixture was heated to 50 °C with stirring. Reaction was diluted with ethyl acetate release, filtered through Celite, washed twice with ethyl acetate, and the filtrate was concentrated in vacuo, the residue was purified by to give the title compound as a brown oil was purified by column 4-trimethylsilylethynylbenzamide (780 mmol g, crude).

According to the analysis of related databases, 698-67-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Kaisheng Beite Pharmaceutical Co., Ltd.; Cai, Xiong; Qian, Changgeng; Liu, Bin; Li, Junqi; Lin, Mingsheng; Qing, Yuanhui; Weng, Yunwo; Wang, Yanyan; Xue, Weicai; You, Huajin; Zhou, Shiqing; (67 pag.)CN105622638; (2016); A;,
Amide – Wikipedia,
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Related Products of 144-80-9, 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 144-80-9 as follows.

Example 155N-({4-[(4-[difluoro(4-fluorophenyl)methyl]-6-{[6-(ethyloxy)-1,3-benzothiazol-2-yl]amino}-2-pyrimidinyl)amino]phenyl}sulfonyl)acetamideA mixture of N-{2-chloro-6-[difluoro(4-fluorophenyl)methyl]-4-pyrimidinyl}-6-(ethyloxy)-1,3-benzothiazol-2-amine (100mg, 0.222mmol), N-[(4-aminophenyl)sulfonyl]acetamide (95mg, 0.444mmol) and 4-toluenesulfonic acid monohydrate (50.6mg, 0.266mmol) in acetonitrile (3m L) was sealed and heated at 1200C for 4 hours in a Biotage “Initiator” microwave. The product was purified by mass-directed autopreparative HPLC (formic acid modifier) to afford the title compound (21 rmg, 0.033mmol, 20% yield) as a white solid. LCMS (Method A): Rt 1.19 minutes; m/z 629 (MH+).

According to the analysis of related databases, 144-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; ALDER, Catherine, Mary; BALDWIN, Ian, Robert; BARTON, Nicholas, Paul; CAMPBELL, Amanda, Jennifer; CHAMPIGNY, Aurelie, Cecile; HARLING, John, David; MAXWELL, Aoife, Caitriona; SIMPSON, Juliet, Kay; SMITH, Ian, Edward, David; TAME, Christopher, John; WILSON, Caroline; WOOLVEN, James, Michael; WO2010/106016; (2010); A1;,
Amide – Wikipedia,
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Application of 1314538-55-0, 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. 1314538-55-0 name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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.

A mixture of 4,6-dichloro-2-(trifluoromethyl)pyrimidine (500 mg, 2.30 mmol, 1.00 equiv), potassium terf-butyl N-[(trifluoroboranuidyl)methyl]carbamate (546 mg, 2.30 mmol, 0.99 equiv), Pd(PPh3)2Cl2 (162 mg, 0.23 mmol, 0.10 equiv), and sodium carbonate (488 mg, 4.60 mmol, 1.99 equiv) in t-butanol (10 mL)/water (2 mL) was stirred for 2 h at 70 C under nitrogen. The solid was filtered off and the filtrate was diluted with water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1/5) to afford the title compound (450 mg, 63%) as a white solid. LCMS [M+H+] 312

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; VERMA, Vishal; SHORE, Daniel; VOLGRAF, Matthew; ESTRADA, Anthony A.; LYSSIKATOS, Joseph; (153 pag.)WO2018/15410; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 120157-96-2, name is Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate, 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 120157-96-2, category: amides-buliding-blocks

Reference Example 63 tert-Butyl 4-hydroxymethylbenzylcarbamate Diisobutylaluminum hydride (25.7 ml, 0.93 M hexane solution) was added dropwise to a THF solution (40 ml) of methyl 4-[N-(tert–butoxycarbonyl)aminomethyl]benzoate (2.54 g) at -78C, followed by stirring at the same temperature for 2 hours. A saturated aqueous ammonium chloride solution (10 ml) and diethyl ether were added dropwise to the reaction solution, followed by stirring at room temperature for 1 hour. Magnesium sulfate was added to the reaction solution, followed by further stirring for 1 hour. After removal of the resulting precipitate by filtration trough celite, the filtrate was concentrated, the thus obtained residue was purified by silica gel column chromatography, and the title compound (1.22 g) was obtained as a colorless oil from the fraction of the elude of n-hexane: ethyl acetate = 10:3. 1H-NMR (400 MHz, CDCl3) delta: 1.43 (9H, s), 4.29 (2H, d, J=5.6 Hz), 4.67 (2H, d, J=5.9 Hz), 4.87 (1H, bs), 7.25 (2H, d, J=8.1 Hz), 7.32 (2H, d, J=8.1 Hz).

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 406233-31-6, name is 4-Fluoro-3-nitrobenzenesulfonamide, 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. Product Details of 406233-31-6

To a stirred solution of (4-methylmorpholin-2-yl)methanamine (400 mg, 3.07 mmol) in THF (25 mL) was added 4-fluoro-3-nitrobenzenesulfonamide (609 mg, 2.76 mmol) followed by triethylamine (1.24 g, 12.28 mmol). After stirring at rt for 16 h, the reaction was concentrated and the resulting crude was diluted with 10% MeOH-DCM (50 mL), and washed with ice-cold water (3 x 50 mL). The organic layer was dried over Na2S04, filtered and concentrated. The crude product was triturated with Et20/pentane to afford Intermediate 17 (600 mg, 65% yield) as a yellow solid. LC/MS (ESI) m/z 331.2 [M+H]+.

The synthetic route of 4-Fluoro-3-nitrobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENO ROYALTIES & MILESTONES, LLC; PINCHMAN, Joseph, Robert; HUANG, Peter, Qinhua; BUNKER, Kevin, Duane; SIT, Rakesh, Kumar; SAMATAR, Ahmed, Abdi; (236 pag.)WO2019/139902; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 138-41-0, 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. 138-41-0 name is Carzenide, 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.

To a solution of (3aS,6aS)-tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(lH)-carboxylate (intermediate 3; 206 mg, 970 muiotaetaomicron), N-methylmorpholine (294 mg, 2.91 mmol) and 4- sulfamoylbenzoic acid (203 mg, 970 muiotaetaomicron) in N,N-dimethylformamide (10 ml) was added 0-(7- azabenzotriazol-l-yl)-N,N,N’,N’ -tetramethyluronium hexafluoro-phosphate (369 mg, 970 muiotaetaomicron) at 0C, then after 10 min the ice-bath was removed. After 16 h the reaction mixture was partitioned between dichloromethane and sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with sat. aq. ammonium chloride solution and brine, dried over magnesium sulfate, filtered and evaporated. After trituration in tert-butyl methyl ether the precipitate was collected by filtration to afford the title compound (348 mg, 91 ). Light yellow solid, MS: 396.6 (M+H)+.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; MATTEI, Patrizio; MAUSER, Harald; TANG, Guozhi; WANG, Lisha; WO2014/139978; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 749927-69-3, 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. 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

100 ml of DMF was added to a 250 ml three-necked flask,A solution of 18.5 g of 5,5-dimethyl-3- (3-trifluoromethyl-4-fluorophenyl) -2-thiamidazol-4-one was successively added with stirring,Ice bath cooling to 0-5 C,Add 3.9 g of sodium hydride in portions.Plus,The ice bath continues to stir for 30 min.13.68 g of 2-fluoro-4-bromobenzoylmethylamine was dissolved in 30 ml of DMF,Slowly add it toIn the reaction solution, control the internal temperature 0-5 C.Plus finished, returned to room temperature, continue to stir 5h,TLC monitoring reaction is completed.The reaction solution was addedTo 500 ml of water, filtered to obtain crude.After drying, column chromatography was performed to obtain 23.9 g of enterine, the yield was 87.3%.

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

Reference:
Patent; Chengdu Yinuo Dabo Pharmaceutical Technology Co., Ltd.; Fu Qingquan; Yue Lijian; Lin Qiang; Liao Xianbo; Zhao Maoxian; Qin Yan; (8 pag.)CN104844520; (2017); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics