Month: September 2021

These common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, 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. Quality Control of tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

To a solution of (1R,3r,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (9.0 g) in DCM (200 mL) was added TEA (11.0 mL) and MsCI (3.7 mL). Theresulting mixture was stirred at 0C for 2 hours, and then diluted with water (100 mL). The reaction mixture was extracted with DCM (2×200 mL). The combined organic layers were washed, dried and concentrated to afford (1 R,3r,5S)-tert-butyl 3-((methylsulfonyl)oxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (12.0 g).

The synthetic route of tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEN, Weichun; IGBOKO, Ebere F; LIN, Xichen; LU, Hongfu; REN, Feng; WREN, Paul Bryan; XU, Zhongmiao; YANG, Ting; ZHU, Lingdong; WO2015/181186; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 598-55-0, 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. 598-55-0, name is Methyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture of 2-naphthol(5 mmol), an aldehyde (5 mmol), and a carbamate(5.5 mmol), CuCl2·2H2O (0.05 mmol) was added. Thereaction mixture was stirred on a preheated water bathat 70C. After completion of the reaction (monitoredby TLC), the reaction mixture was cooled to RT.washed with H2O/EtOH (v/v = 1/1), and recrystallizedfrom H2O/EtOH (v/v = 2/3). The products were characterized by IR, 1H NMR, 13C NMR, LC/MS andelemental analysis.

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, Methyl carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Song, Zhiguo; Liu, Lianli; Sun, Xiaohu; Cui, Yan; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 53; 6; (2014); p. 740 – 745;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application 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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 154350-29-5, 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. 154350-29-5, name is Cyclopropanesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 7: Synthesis of (IS, 4R, 6S, 14S, 18R)- [7-cis-4-Cyclopropanesulfonylaminocarbonyl-12-cyclopropyl-18-(tert-butyldimethylsilyloxy)- 2, 15-dioxo-3, 12,16-triaza-tricyclo[14.3.0. (f’6]nonadec-7 -en-14-yl] carbamic acid, tert-butyl ester.; (15, AR, 65, 145, 18R)-7-c-14-tert-Butoxycarbonylamino-18-(tert- butyldimethylsilyloxy)-2,15-dioxo-3, 12,16-triazatricyclo[ 14.3.0.04’6]nonadec-7-ene- 4-carboxylic acid (490 mg, 0.79 mmol) was dissolved in 15 mL of THF and treated with CDI (179 mg, 1.10 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere.) After refluxing the reaction mixture for two hours, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (134 mg, 1.10 mmoL) and DBU (168 mg, 1.10 mmoL). After stirring overnight at rt, the THF was removed by rotary evaporation. The residue was dissolved in water and IN HCl was added until the pH = 5. This aqueous solution was extracted with EtOAc (3x). The combined EtOAc extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by flash column, eluting with 3percent methanol in methylene chloride, gave 300 mg (53percent) Of (IS”, 4R, 65, 145, 18R)- [7-c-4-Cyclopropanesulfonylaminocarbonyl-12- cyclopropyl- 18-(tert-butyldimethylsilyloxy)-2, 15 -dioxo-3 ,12,16-triaza- tricyclo[14.3.0.04’6]nonadec-7-en-14-yl]carbamic acid, tert-butyl ester as a white solid: LC-MS (Phenomenex 10 mum Cl 8 HPLC column: 3.0×50 mm length. Gradient: 100percent Solvent A/0percent Solvent B to 0percent Solvent A/100percent Solvent B. Gradient time: 2 min. Hold time: 1 min. Flow rate: 5 mL/min. Detector Wavelength: 220 nM. Solvent A: 10percent MeOH / 90percent H2O / 0.1percent TFA. Solvent B: 10percent H2O / 90percent MeOH / 0.1percent TFA.) (Retention time: 2.40 min), MS m/z 724 (M++l).

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; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64061; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference 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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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 4-Methoxybenzenesulfonamide

General procedure: Under the argon atmosphere, a Schlenk tube (15 mL) equipped with a magnetic bar was loaded with the sulfonamide 1 (0.5 mmol), sodium arylsulfinates 2 (0.6 mmol, 1.2 equiv.), Pd(MeCN)2Cl2 (6.5 mg, 5 mol%) and AgOAc (166.9 mg, 1.0 mmol) in one portion. Then, the mixture of 1,4-dioxane/DMSO (3.5 mL in a 9:1 ratio) was added to obtain a clear solution and the reaction mixture was allowed to stir at 120 C for 24 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a petroleum ether and ethyl acetate (3/1) as eluent to give the N-aryl sulfonamides 3 in noted yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1129-26-6, its application will become more common.

Reference:
Article; Zhao, Zijian; Lian, Yan; Zhao, Chang; Wang, Bing; Synthetic Communications; vol. 48; 12; (2018); p. 1436 – 1442;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature 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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route 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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 703-12-8, 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. 703-12-8 name is 4-Bromo-N-methylbenzenesulfonamide, 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.

Step b: 4-(lambdar-Methylsulfamoyl)phenylboronic acid; To a solution of 4-bromo-iV-methyl-benzene sulfonamide (24.9 g, 0.1 mol) and B(O1Pr)3 (28.2 g, 0.15 mol) in THF (200 mL) was added n-BuLi (100 mL, 0.25 mol) at -70 0C. The mixture was slowly warmed to 0 0C, then 10% HCl solution was added until pH 3-4. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and evaporated under reduced pressure to give 4-(iV-methylsulfamoyl)phenylboronic acid (22.5 g, 96%), which was used in the next step without further purification. 1H NMR (DMSO-J6, 300 MHz) delta 8.29 (s, 2 H), 7.92 (d, J = 8.1 Hz, 2 H), 7.69 (d, J = 8.4 Hz, 2 H), 2.36 (d, J = 5.1 Hz, 3 H).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/56341; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16313-66-9,Some common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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 2-amino-5-bromo-benzamide (29.2 g, 136 mmol) andtriethylamine (25.0 mL, 173 mmol) in THF (500 mL) was added dropwise o-anisoyl chloride (24.0 g, 140 mmol). Stirring at room temperature was continued for 3 h, after which the formed precipitate was filtered and washed once with THF and twice with dichloromethane yielding 2-(o-anisoyl)-amino-5-bromo-benzamide (51.4 g, 84%) with 1 equivalent of triethylamine hydrochloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromobenzamide, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/28904; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics