Category: amides-buliding-blocks

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;,
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Synthetic Route of 201162-53-0,Some common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, molecular formula is C11H20N2O2, 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 solution of /er/-butyl 3,8-diazabicyclo[3.2. l]octane-3-carboxylate (1.0 equiv) and DIEA (2.0 equiv) in dry DCM at 0C was added BrCN (1.5 equiv). The mixture was stirred at 0C for lh and then at rt overnight. The reaction mixture was washed with water and brine to afford /c/7-butyl 8-cyano-3,8-diazabicyclo[3.2.l]octane-3-carboxylate which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Boc-3,8-Diazabicyclo[3.2.1]octane, its application will become more common.

Reference:
Patent; ESCALIER BIOSCIENCES B.V.; MOHAN, Raju; NUSS, John; HARRIS, Jason; YUAN, Shendong; (144 pag.)WO2019/177996; (2019); A1;,
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Application of 121492-06-6, 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 121492-06-6 as follows.

202cU.l-dimethylethyl (2-{r8-(2,6-difluorophenylV4-r2-niethyl-S-(rr2- phenylethvPaminol carbonyllphenviy7-oxo-7,8-dihydrorhoyrido[23-cf1pyrimidin-2- yli amino } ethypmethylcarbamateTo the solution of 3-[8-(2,6-difluorophenyl)-2-(methylsulfmyi)-7-oxo-7,8- dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-(2-phenylethyl)benzainide (156 mg, 0.28 mmol) in dichloromethane (11 mL) was added 1,1-dimethylethyl (2- aminoethyl)methylcarbamate (75 muL, 0.42 mmol) and triethylamine (78.7 muL, 0.56 mmol). The reaction mixture was stirred at room temperature for 16 hours then applied to the flash chromatograph to afford the titled compound 147 mg (79 %). LC-MS m/z 669 (M + H)+; 1H-NMR (MeOD) 1.30 (m, 9 H), 2.31 (m, 3H), 2.65 (m, 2 H), 2.76 (m, 1 H), 2.92 (m, 2 H), 3.22 (m, 2 H), 3.45 (m, 1 H), 3.60 (m, 2 H), 6.35 (m, 1 H), 7.19 (m, 2 H), 7.26 (m, 5 H), 7.43 (m, 1 H), 7.49 (m, 1 H), 7.60 (m, 1 H), 7.74 (m, 1 H), 7.97 (m, 1 H).

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; GLAXO GROUP LIMITED; WO2006/104915; (2006); A2;,
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Electric Literature of 53844-02-3, A common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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.

To a stirred solution of bromide (1 mmol) and 4-amino-1-butanol (0.36 g, 4 mmol, 4 eq.) in anhydrous DMF (10 ml) under N2, was added anhydrous K2CO3 (0.276 g, 2 mmol, 2 eq.) and sodium iodide (15 mg, 0.1 mmol, 0.1 eq.). The reaction was stirred for 72 hours at room temperature, until reaction complete. The DMF was evaporated in vacuo and dried exhaustively under high vacuum. The resulting oily solid was redissolved in CH2Cl2 (100 ml) and washed with water (4 x 50 ml). The combined aqueous extracts were then washed with CH2Cl2 (40 ml) and the CH2Cl2 extracts dried over anhydrous Na2SO4. The CH2Cl2 was evaporated in vacuo to give a 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; IC-VEC LIMITED; EP918790; (2004); B1;,
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Related Products of 4793-24-2, These common heterocyclic compound, 4793-24-2, name is 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, 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.

Compound 1 was dissolved in 1 mL of compound 2 and heated to 10OC and monitored by TLC until complete. When complete, as indicated by TLC, the reaction was removed from the heat. A pale yellow goo remained, containing crystals. To this mixture was added IM HCl and this stirred for 10 min. At this time, a precipitate fell out of solution that was subsequently filtered to yield the pure product as indicated by NMR.IH NMR: 8.25 (s, IH), 7.5-7.2 (m, 5H), 6.71 (s, IH), 4.54 (s, 2H), 4.0 (s, IH), 3.3 (s, 2H).Ms API-ES Neg. Scan calculated for C14H12C1N2O4S- 339.02. ; obtained 339.2

The synthetic route of 4793-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLYNN, Gary, A.; YOOL, Andrea, J.; MIGLIATI, Elton, Rodrigues; RITTER, Leslie, S.; WO2008/52190; (2008); A2;,
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Related Products of 154350-29-5, The chemical industry reduces the impact on the environment during synthesis 154350-29-5, name is Cyclopropanesulfonamide, I believe this compound will play a more active role in future production and life.

To a solution of cyclopropanesulfonamide (6 g, 50 mmol) in DCM (50 ml) were added triethylamine (7.5 ml, 74 mmol) followed by DMAP (0.3 g, 7.5 mmol) and di-tert-butyl dicarbonate (13 g, 59 ml) and the reaction was left stirring overnight. The solvent was removed; water, 2N HCl (40 ml) and ethyl acetate were added. The organic layer was washed with brine, dried over magnesium sulfate and evaporated to give Boc-cyclopropanesulfonamide as a white solid, used on the next step without further purification. Yield 9.73 g (88percent).

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, Cyclopropanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INTERMUNE, INC.; US2011/82182; (2011); A1;,
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Application of 37045-73-1, 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. 37045-73-1, name is 3-(Methylsulfonamido)aniline belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Chloro-6,7-dimethoxy-quinazoline (100 mg, 0.4500 mmol) and 1H-indazol-6-amine (59.27 mg, 0.4500 mmol) were mixed in MeCN (2 mL) and irradiated in a CEM microwave at 100 C for one hour. The reaction mixture was allowed to cool and then passed through a short pad of silica. After concentration of the filtrate, the resultant solid was washed sequentially with acetonitrile and diethyl ether and dried in vacuo to give 16 (0.13g, 81%) as a light brown solid. 1H NMR (DMSO-d6) delta 13.21 (br s, 1H), 11.37 (s, 1H), 8.84 (s, 1H), 8.30 (s, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.41 (d, J=8.6 Hz, 1H), 7.34 (s, 1H), 4.03 (s, 3H), 4.01 (s, 3H)

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, 3-(Methylsulfonamido)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jordan, Allan M.; Begum, Habiba; Fairweather, Emma; Fritzl, Samantha; Goldberg, Kristin; Hopkins, Gemma V.; Hamilton, Niall M.; Lyons, Amanda J.; March, H. Nikki; Newton, Rebecca; Small, Helen F.; Vishwanath, Swamy; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 11; (2016); p. 2724 – 2729;,
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Related Products of 67442-07-3, 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 67442-07-3 as follows.

To a THF solution of (S)-1-bromo-2-methyloxy-3-(1-methyloxyheptyl)benzene (9, 12.5 g) obatined in the second step was added dropwise a 2M isopropyl magnesium chloride THF solution (44 mL) under ice-cooling. After the reaction solution was stirred at 45°C for 3 hours, N-methyloxy-N-methyl-2-chloroacetamide(10, 3.5 g) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was extracted with ethyl acetate, and purified by silica gel chromatography to obtain (S)-2-chloro-1-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)ethanone (11). NMR (CDCl3) delta ppm: 0.87 (3H, t, J = 6.8 Hz), 1.2 – 1.82 (10H, m), 3.22 (3H, s), 3.78 (3H, s), 4.53 (1H, m), 4.73 (2H, m), 7.24 (1H, t, J = 7.6Hz), 7.52 (1H, dd, J = 7.6 Hz, J = 1.8 Hz), 7.60 (1H, dd, J = 7.7 Hz, J = 1.8Hz)

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi&Co., Ltd.; EP2184279; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of tert-Butyl methyl(2-(methylamino)ethyl)carbamate

Brought 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione (1-3) (500 mg, 1.81 mmol) , tert-butyl methyl(2-(methylamino)ethyl)carbamate (22-1) (1.99 mmol) and DIEA (787 4.52 mmol) up in NMP (3.62 mL ) and heated to 90°C overnight. Cooled the mixture to r.t. and loaded directly onto reversed phase isco 10-100percent ACN/water w TFA. Lyophilized the combined fractions to give tert-butyl (2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4- yl)(methyl)amino)ethyl)(methyl)carbamate (800 mg, 1.79 mmol, 99.5 percent) as a yellow solid. LC/MS (ES+): m/z 467 [M+Na]+

The synthetic route of 112257-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; MICHAEL, Ryan, E.; (790 pag.)WO2017/197056; (2017); A1;,
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Electric Literature of 57561-39-4, These common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)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.

Step 1. Synthesis of ethyl {2-[(tert-butoxycarbonyl)(methyl)amino]ethoxy}acetate A solution of ethyl 2-diazoacetate (0.900 mL, 8.56 mmol), tert-butyl (2-hydroxyethyl)(methyl)carbamate (1.50 g, 8.56 mmol) and rhodium(II) acetate dimer (0.380 g, 0.856 mmol) in CH2Cl2 (10.0 mL) were used to carry out the reaction. After the reaction was stirred at room temperature for 16 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-10% ethyl acetate in n-hexane) to give ethyl {2-[(tert-butoxycarbonyl)(methyl)amino]ethoxy}acetate (0.690 g, 31%). 1H NMR (CDCl3, 300 MHz) delta 4.28-4.18 (m, 2H), 4.07 (br s, 2H), 3.65 (br s, 2H), 3.42 (br s, 2H), 2.93-2.92 (m, 3H), 1.45-1.44 (m, 9H), 1.25 (br t, 3H).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National Health Research Institutes; Ueng, Shau-Hua; Yeh, Shiu-Hwa; Lin, Shu-Yu; Shih, Chuan; (329 pag.)US2017/253569; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics