Month: September 2021

These common heterocyclic compound, 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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. SDS of cas: 1314538-55-0

[01374] To a 3000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 5-[4-chloro-5-(difluoromethyl)pyridin-2-yl] -2-(trifluoromethyl)pyrimidine (20 g, 64.59 mmol, 1.00 equiv), ethanol (2000 mL), water (400 mL), potassium tert-butyl N-[(trifluoroA4boranyl)methyl]carbamate (20 g, 84.36 mmol, 1.30 equiv), sodium carbonate (22 g, 207.57 mmol,3.20 equiv) and Pd(PPh3)2C12 (5 g, 7.12 mmol, 0.11 equiv). The reaction mixture was first stirred at room temperature for 30 mm and at 80C overnight and filtered. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel colunm eluted with ethyl acetate/petroleum ether (0:1-1:6) to afford 14 g (54%) of tert-butyl N- [[5-(difluoromethyl)-2-[2-(trifluoromethyl)pyrimidin-5 – yl]pyridin-4-yl]methyl]carbamate as a light yellow solid.

The synthetic route of Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 37073-15-7, 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. 37073-15-7 name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, 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.

General procedure: Et3N (0.22 g, 2.2 mmol) was added to a suspension of 2,2′-AzPy-dicarboxylic acid 2a-c (0.275 g, 1 mmol) in anhydrous DMF (4 mL) in a dried 10 mL heavy-walled Pyrex tube containing a long stir bar. BtSO2Me (0.43 g, 2.2 mmol) was added to this solution and exposed to microwave irradiation (30 W) for 15 min at 70 C with vigorous stirring and simultaneous air cooling. After completion of the reaction, the mixture was cooled to r.t. and poured onto crushed ice-water mixture (~20 g). The precipitate formed was filtered and washed with aq 10% Na2CO3 (3 × 5 mL), H2O, and Et2O. The solid was dried to yield 2,2′-AzPy-diacylbenzotriazoles 3a-c as microcrystals (Table 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, and friends who are interested can also refer to it.

Reference:
Article; Avan, Ilker; Synthesis; vol. 48; 3; (2016); p. 365 – 378;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 131818-17-2, name is tert-Butyl (4-bromophenyl)carbamate, molecular formula is C11H14BrNO2, 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. Quality Control of tert-Butyl (4-bromophenyl)carbamate

0.263 mL (1.1 eq. ) iodomethane are added dropwise at room temperature to a stirred suspension of 1.1 g (4 mmol) (4-bromo-phenyl)-carbamic acid tert-butyl ester and 2 g (1.6 eq. ) cesium carbonate in 15 mL DMF. After stirring for an additional18 hours, the reaction mixture is extracted with WATER/ETHYL acetate and the combined organic phases are washed with brine, dried over magnesium sulfate and evaporated to yield the desired product as a colorless oil, which is 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 131818-17-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/87684; (2004); 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. 192436-83-2, name is 4-Bromo-N-methoxy-N-methylbenzamide, A new synthetic method of this compound is introduced below., Recommanded Product: 192436-83-2

To a solution of ibromo-.3.trifluoromethyl)benzene (800 mg, 3.56 mmol) in 1() mL of THF was added Mg (129.6 rng, 5.33 mmoi) under nitrogen protection and stirred at 80CC for 2 h. Then the mixture was added to a solution of 4-hromoN-methoxy-Nmethylhenzamide (433.9 mg, 1.78 mmol) in THF (6mL) at 0 C under nitrogen protection and stirred at 20 C for 12 h. The mixture was poured into aq.N1-14C1 (150 mL) and extracted with ethyl acetate (120 mLx3).The organic layer was dried over Na2 SO4 and concentracted in vacuo to give the residue, which was purified with pre HP LC to give (4-bromophenyl)(3.-(trifiuorornethyi)phenyi)methanone. 1HNMR (400MHz, CDC13): oe = 8.04 (s, IH), 7.95 (d, J=7.8 Hz, IH), 7.87 (d, J=.() Hz, 1H),7.67 (s, 4H), 7.66 7.62 (m, il-i) ppm.

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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (261 pag.)WO2016/106628; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, molecular formula is C10H19NO3, 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. COA of Formula: C10H19NO3

To a solution of PPh3 (244 mg, 0.90 mmol) in anhydrous tetrahydrofuran (10 mL) was added DIAD (188 mg, 0.90 mmol) by syringe at 05 C, followed by a solution of tert-butyl (1 -(hydroxymethyl)cyclopropyl)methylcarbamate (110-13) (178 mg, 0.90 mmol) in anhydrous tetrahydrofuran (5 mL). The resulting mixture was poured into a solution of compound 308-7 (100 mg, 0.30 mmol) in anhydrous tetrahydrofuran (5 mL) at ambient temperature and stirred for 10 mm. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (dichloromethane/ethyl acetate: 5/1) to afford the title compound 309-17 as a yellow solid (100 mg, crude). LCMS: 522.3 [M+1] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 153248-46-5, its application will become more common.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); 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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Step 14-sulfamoylbenzoyl azide (JS129)4-sulfamoylbenzoic acid (1 .00 g, 4.97 mmol), triphenylphosphine (2.61 g, 9.94 mmol) and sodium azide (0.388 g, 5.96 mmol) were suspended in anhydrous acetone (10 ml). To this milky white suspension was added trichloroacetonitrile (0.997 ml, 9.94 mmol) drop wise and the reaction was left to stir at RT for 18 h. The solvent was removed in vacuo and the resulting dark yellow slurry was diluted with CH2CI2 and washed with H20 and brine, dried (MgS04), filtered and concentrated in vacuo. Flash chromatography (Pet Ether; 3:1 to 2:1 to 1 :1 Pet Ether/EtOAc) afforded the title compound as a white solid (906.9 mg, 4.01 mmol, 80.7%). Mpt: 1 18 C; Rf = 0.23 (1 :1 Pet Ether/EtOAc); IR (vmax/cm”1, thin film): 3362 (aromatic C-H stretch), 3258 (N-H stretch), 2137 (N=N=N stretch), 1687 (CO stretch), 1339 (S=0 stretch, asymmetrical), 1238, 1 155 (S=0 Symmetrical stretch); 1H NMR (600 MHz, CD3OD): deltaEta = 8.02 (ap.d, J = 6.9 Hz, 2H, 4-H), 8.18 (ap.d, J = 6.8 Hz, 2H, 3-H); 13C NMR (150 MHz, CD3OD): 5C = 127.6 (C-4), 131.0 (C-3), 134.9 (C-2), 150.2 (C-5), 172.8 (C-1 ); LRMS/HRMS m/z (ES+): no product mass present; Anal. Calcd. for C7H6N403S: C, 37.17; H, 2.67; N, 24.77. Found C, 37.27; H, 2.49; N, 24.40%.

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; UCL BUSINESS PLC; BIRKBECK COLLEGE; WAKSMAN, Gabriel; TABOR, Alethea; SAYER, James; WALLDEN, Karin; WO2012/168733; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 180079-94-1, 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. 180079-94-1, name is tert-Butyl 3-aminophenethylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step-4: Synthesis of 3-(2-aminoethyl) aniline A solution of tert-butyl (3-aminophenethyl) carbamate (3.0 g, 12.71 mmol, 1 eq) in TFA (10 mL) was stirred at room temperature for 1 h. The reaction liquid was concentrated to obtain, 3-(2-aminoethyl) aniline (2.5 g, crude) as brown liquid.

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 3-aminophenethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below., Recommanded Product: 61903-11-5

Bromopyrazole is mixed with K2CO3 and KI in 10 volumes of acetone at room temperature and N-acetylhomopiperazine was added over 1 hr. The reaction mixture was stirred until the reaction was complete. The mixture was filtered, removing the inorganics, washed with acetone and distilled to 2 volumes. The freebase was extracted into methyl THF/ EtOH and washed with NaCl and NaHCO3. The solvent was replaced with EtOH, a strength of the solution was determined, and 0.93 eq of HCl based on the available freebase was added to a mixture of acetone, ethanol and water. Careful monitoring of the pH yielded crystalline product in a 70% overall yield and the desired form 1.;To a cylindrical, jacketed 3 L reactor equipped with nitrogen inerting, agitator, condenser/distillation head, and temperature control, 5-bromo-pentanoic acid [5- (4-methoxy-phenyl)-lH-pyrazol-3-yl]amide (0.15 kg, 0.426 mol), potassium carbonate (0.059 kg, 0.426 mol), potassium iodide (0.071 kg, 0.426 mol), and acetone (1.18 kg, 1.5 L) were added (at 20 0C) to form a white mixture. The mixture was stirred (235 rpm) at 25-30 0C for a minimum of 15 min. N-acetylhomopiperazine (0.062 kg, 0.057 L, 0.434 mol) was added via addition funnel to the reactor over a minimum of 45 min., maintaining the temperature in the range of 25-30 0C. The addition funnel was rinsed with 0.05 L acetone. A white mixture persisted. The mixture was stirred (235 rpm) in the range of 25-30 0C for a minimum of 16 h, forming a white/yellow mixture. The reaction progress was monitored by HPLC and was considered complete when there was < 2% of the starting material (bromopyrazole) and < 2% of the iodopyrazole present. [00240] The reactor contents were cooled to 5-15 0C over a minimum of 15 min with agitation (295 rpm) to form a white/yellow mixture that was then stirred for a minimum of 1 h. To remove inorganics, the mixture was then filtered on a Buchner funnel with filter paper using house vacuum for 1.5 min. The cake was washed twice with acetone (total of 0.24 kg, 0.30 L) at 5-15 0C. The wash was combined with the mother liquor from the prior filtration and used to rinse the reactor. The filtrate was concentrated to a volume of approximately 0.45 L to form a clear solution.

The synthetic route of 61903-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; SIENA BIOTECH S.P.A.; WO2009/91832; (2009); 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 104060-23-3 as follows. HPLC of Formula: C13H19NO3

193-2 2-(4-tert-Butoxycarbonylaminophenyl)ethyl-4-(2-bromo-5-methoxybenzyl)piperidine Methanesulfonyl chloride (120 mul, 1.56 mmol) was added dropwise to a solution of 2-(4-tert-butoxycarbonylaminophenyl)ethanol (354 mg, 1.56 mmol) and triethylamine (430 mul, 3.12 mmol) in dichloromethane (5 ml) under ice-cooling, and the reaction mixture was stirred as it was for 2 hours. The solvent was distilled off and the resulting residue was suspended in acetonitrile (5 ml) together with a free compound obtained by treating the compound of Example 1 (500 mg, 1.56 mmol) by the same method as in Example 11, potassium carbonate (431 mg, 3.12 mmol) and potassium iodide (259 mg, 1.56 mmol). The resulting suspension was stirred at 60 C. for 1 hour, heated under reflux for 4 hours, and then allowed to cool. After filtration, the filtrate was concentrated and the residue was purified by a silica gel column chromatography (chloroform/methanol=50/1 to 20/1) to obtain the title compound (587 mg, 73%) as a colorless oil.

According to the analysis of related databases, 104060-23-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO PHARMACEUTICALS COMPANY LIMITED; US2003/191126; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 2227-79-4, These common heterocyclic compound, 2227-79-4, name is Benzothioamide, 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 solution of benzothioamide (3.00 g, 21.87 mmol) in EtOH (70 mL) was treated dropwise with ethyl bromopyruvate (5.10 g, 26.2 mmol) and stirred at room temperature for 30 min before being heated at reflux for 1.5 h. The cooled mixture was diluted with ethyl acetate (200 mL), washed (aqueous NaHC03, brine), dried over anhydrous MgSO4 and evaporated. The residue was purified on the ISCO using a REDISEP 80 g column (10 to 20% EtOAc-hexane) to give the title compound (4.82 g, 94%) as a yellow oil. LCMS (APCI): calcd for C12H12NO2S [M+H]+ m/z 234.05, found 234.1. 1H NMR (CDCl3, 400 MHz) delta ppm: 8.14 – 8.19 (m, 1H), 7.98 – 8.07 (m, 2H), 7.41 – 7.51 (m, 3H), 4.46 (q, J= 7.2 Hz, 2H), 1.44 (t, J= 7.2 Hz, 3H)

The synthetic route of 2227-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; BANVILLE, Jacques; REMILLARD, Roger; RUEDIGER, Edward H.; DEON, Daniel H.; GAGNON, Marc; DUBE, Laurence; GUY, Julia; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; MAXWELL, Brad D.; WONG, Pancras C.; WO2013/163279; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics