Month: September 2021

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. 4141-08-6, name is 2-Amino-N-methylbenzamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H10N2O

General procedure: For the 5-subsititution was H, F or Cl, the procedure was as follows: A mixture of compound 7 (0.79 g, 5.25 mmol), 5-substituted-2,4-dichloropyrimidine (5 mmol) and DIPEA (1.05 mL,6 mmol) in i-PrOH was heated under reflux for 6 h.Water (100 mL)was added and the solid was filtered off, washed with water and driedto obtain compounds 10a-10c. For the 5-subsititution was methyl or methoxy, the procedure was as follows: To a mixture of compound 7 (1.26 g, 8.4 mmol) and5-substituted-2,4-dichloropyrimidine (8 mmol) was added NaH (60%, 0.38 g, 9.6 mmol) in DMF (6 mL) under ice bath. Then the mixture was stirred for 24 h at room temperature.Water was added dropwise to stop the reaction. The reaction mixture was extracted withdichloromethane (20 mL x 3), and the combined organic layer waswashed with brine (15mL x 2), dried over anhydrous Na2SO4 and concentrated under vacuum to afford the crude product. The residue was purified by column chromatography to obtain compound 10d and 10e.

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:
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 147751-16-4, These common heterocyclic compound, 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, 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.

Boc-N-methanesulfonamide (11.0 g, 56.3 mmol), trimethylphosphine (56.1 mL of a 1.0 M solution in tetrahydrofuran, 56.1 mmol), and a 40 wt. % solution of diethyl azodicarboxylate in toluene (25.6 mL, 56.0 mmol) were added sequentially to a solution of (4-benzylsulfanyl-5-nitro-thiophen-3-yl)-methanol (10.52 g, 37.4 mmol) in tetrahydrofuran (300 mL) at 25 C. The mixture was stirred for 3.5 h at 25 C., and then was concentrated in vacuo. Purification of the residue by flash column chromatography (Merck silica gel 60, 40-63 mum; 20% ethyl acetate in hexanes) afforded the desired product, Boc-N-(4-benzylsulfanyl-5-nitro-thiophen-3-ylmethyl)-methanesulfonamide (9.79 g, 21.3 mmol, 57%), as a dark brown oil. 1H NMR (400 MHz, CDCl3) delta: 1.50 (9H, s), 3.29 (3H, s), 4.19 (2H, s), 4.68 (2H, s), 7.15-7.18 (2H, m), 7.22-7.25 (3H, m), 7.40 (1H, s).

The synthetic route of 147751-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anadys Pharmaceuticals, Inc.; US2012/316156; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 2360-20-5,Some common heterocyclic compound, 2360-20-5, name is 3,4-Diaminobenzenesulfonamide, molecular formula is C6H9N3O2S, 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.

General procedure: Benzaldehyde (73 muL, 0.72 mmol, 1 eq) was dissolved in EtOH (2-5 mL), and sodium metabisulfite (205 mg, 1.08 mmol, 1.5 eq) in H2O (1-2 mL) was added in dropwise. The reaction mixture was stirred at rt overnight. Reaction mixture was diluted with EtOH, cooled and formed precipitate was filtered and dried (128 mg). The mixture of this salt (124.6 mg, 0.596 mmol, 1.5 equiv) and 3-amino-4-(methylamino) benzenesulfonamide (3) (80 mg, 0.397 mmol, 1 equiv) in 5 mL DMF was heated at 60? for 6 h. Reaction mixture was diluted with water and formed precipitate was filtered. The crude product was purified by flash chromatography on silica gel (12 g), eluting with a gradient of 0-11% MeOH in DCM to give 4a (74.5 mg, 64.8% yield) as a white powder. Mp 266-268.6 C. 1H NMR (400 MHz, DMSO-d6): delta 3.92 (3H, s), 7.32 (2H, s), 7.58-7.60 (3H, m), 7.76-7.81 (2H, m), 7.85-7.88 (2H, m), 8.14 (1H, s); 13C NMR (100 MHz DMSO-d6): delta 32.05, 111.05, 116.93, 119.93, 128.75, 129.41, 129.48, 130.12, 138.25, 138.45, 141.53, 155.41; HRMS m/z calculated for C14H13N3O2S [M+H]+ 288.0807, found: 288.0794.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Diaminobenzenesulfonamide, its application will become more common.

Reference:
Article; Cal??kan, Burcu; Banoglu, Erden; Guer Maz, Tu?ce; Nocentini, Alessio; Supuran, Claudiu T.; Uslu, Azize Gizem; Bioorganic Chemistry; vol. 95; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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 94838-59-2, HPLC of Formula: C13H20N2O2

2-(1,3-dioxo-2Hisoindol-2-yl)-4- thiazolylacetic acid(Formula 3-1) (CAS No. 954268-27-0) (20.0 g, 0.069 mole) and Hydroxybenzotriazole hydrate (11.9 g, 0.077 mole) was dissolved in dichloromethane (160 ml), and then cooled to 0 to 5 C. N, N-dicyclohexylcarbodiimide (14.3 g, 0.069 mole) was dissolved in dichloromethane (40 ml) and slowly added dropwise to the cooled mixture, and then Maintaining temperature at 0 ~ 5 and stirred for 30 min. To the suspended reaction solution [2- (4-aminophenyl) Ethyl] carbamic acid tert-butyl ester (Formula 2-1) (CAS No. 94838-59-2) (16.4 g, 0.069 mole) and Triethylamine (7.02 g, 0.069 mole) was added thereto and stirred at room temperature (20 to 25 C) for 24 hours. After completion of the reaction, the reaction solution was cooled to 0 to 5 C, stirred for 12 hours, and filtered. After filtration, the residue was washed with dichloromethane (20 ml), and the filtrate was obtained. The residue was extracted with 200 ml of brine solution. The extraction was carried out three times. An organic layer was obtained, and the solid obtained by concentration under reduced pressure at 35 to 40 C was vacuum-dried at 35 to 40 C for 15 hours to obtain the compound of Formula 5-1 (30.5 g, yield 87%).

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; Nebular Perm Nosebleed A Co., Ltd.; Jeong In-hwa; Lee In-gyu; Mo Gil-ung; Han Hae-su; Han Ga-ram; Shin Jae-won; Kim Hyeon-jeong; Kim A-reum; Jeong Gi-won; Ahn Ji-hun; (23 pag.)KR2018/138058; (2018); A;,
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 402-46-0 as follows. 402-46-0

A round bottom flask was charged with 4-fluorobenzenesulfonamide (945 mg, 5.4 mmol), L-proline-t-butyl ester HCl (1.24 g, 6 mmol), and cesium carbonate (4.2 g, 12 mmol) and suspended in 10 ml anhydrous DMSO. The mixture was placed in a preheated oil bath and equipped with a condenser, and heated under nitrogen at 168 oC overnight. HPLC analysis of the mixture indicated complete conversion of the benzenesulfonamide starting material. The mixture was transferred to an Erlenmeyer flask, the reaction pot was diluted with 2 ml of concentrated HCl, and added to the mixture in the Erlenmeyer flask and allowed to stir. The aqueous was then extracted with ethyl acetate (3 x 50 ml), and the combined extracts were washed with water (3 x 15 ml). The volatiles were then removed under vacuum, and 1.24 g of crude material was obtained. The desired intermediate was isolated using MPLC, utilizing a 0 to 60% gradient of acetone in DCM, affording 0.56 g (41%):1H NMR (300 MHz, DMSO-d6)d ppm 7.58 (d, J= 9.0 Hz, 2H), 6.98 (s, 2H), 6.54 (d, J= 9.0 Hz, 2H), 4.28 (d, J= 8.4 Hz, 1H), 2.35-2.22 (m, 2H), 2.04-1.96 (m, 2H).

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ahmed, Gulzar; Elger, Walter; Meece, Frederick; Nair, Hareesh B.; Schneider, Birgitt; Wyrwa, Ralf; Nickisch, Klaus; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5569 – 5575;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 183059-24-7,Some common heterocyclic compound, 183059-24-7, name is tert-Butyl 2-hydroxy-2-methylpropylcarbamate, molecular formula is C9H19NO3, 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 mixture of intermediate 16 (3.0 g, 15.9 mmol, crude) in anhydrous DCM (50 mL) was added DAST (2.3 mL, 17.4 mmol) at -78 C under a nitrogen atmosphere. The mixture was stirred at -78 C for 1 h, and allowed to warm to rt overnight. The mixture was then cooled to 0 C, and quenched by addition of saturated aqueous layer NaHCO3(30 mL) with stirring at 0 C slowly. The mixture was separated, and the aqueous layer was extracted with DCM (2x 20 mL). The combined organic layers were washed with brine (2 x 30 mL), dried, filtered and concentrated under vacuum to give the crude intermediate 17 (2.5 g, 76% crude), which was used directly in next step without purification. 1H NMR: (CDCI3): delta 4.82 (br, 1H), 3.30-3.35 (d, = 6.0 Hz, 1H), 3.24-3.26 (d, = 6.0 Hz, 1H), 1.44 (s, 9H), 1.37 (s, 3H), 1.35 (s, 3H).19F NMR: (CDC13400 MHz): delta -144.93.

The synthetic route of 183059-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; VITAE PHARMACEUTICALS, INC.; BUKHTIYAROV, Yuri; CACATIAN, Salvacion; DILLARD, Lawrence, Wayne; DORNER-CIOSSEK, Cornelia; FUCHS, Klaus; JIA, Lanqi; LALA, Deepak, S.; MORALES-RAMOS, Angel; RAST, Georg; REEVES, Jonathan; SINGH, Suresh, B.; VENKATRAMAN, Shankar; XU, Zhenrong; YUAN, Jing; ZHAO, Yi; ZHENG, Yajun; WO2013/134085; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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 150349-36-3, Application In Synthesis of 3-(N-Boc-N-methylamino)propylamine

To a dichloromethane solution of 1 ,1 -dimethylethyl (3- aminopropyl)methylcarbamate (1.07 g, 5.67 mmol) was added Lambda/-(1 -benzothien-2- ylcarbonyl)-L-leucine (1.50 g, 5.15 mmol), 3,4-dihydro-3-hydroxy-4-oxo-1 ,2,3- benzotriazine (HOOBT) (21 mg, 0.13 mmol), and N-methylmorpholine (NMM) (0.91 ml, 8.25 mmol). The mixture was stirred several minutes whereupon EDCHCI (1.09 g, 5.67 mmol) was added. The reaction mixture was stirred overnight at RT. The solution was washed with 10% citric acid and brine, dried (MgSO4), filtered and concentrated to a solid. Purification by silica gel column chromatography (30%-70% ethyl acetate/hexane) gave the product as a white solid in 85% yield (1.9g): MS (m/z): 362 (M+H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(N-Boc-N-methylamino)propylamine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/29210; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 2439-77-2, These common heterocyclic compound, 2439-77-2, name is 2-Methoxybenzamide, 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.

Under argon, tert-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (200 mg, 447 muiotaetaomicron), 2-methoxybenzamide (169 mg, 1.12 mmol), Tripotassium phosphate (133 mg, 626 muiotaetaomicron), tBuBrettPhos (13.0 mg, 26.8 muiotaetaomicron), and tBuBrettPhos Pd G3 (22.9 mg, 26.8 muiotaetaomicron) were dissolved in l-Methoxy-2-propanol (5.0 ml, 52 mmol). The mixture was stirred at 110 C for 16 h and then purified via reverse phase chromatography (Method: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / solvents: A = water (0,01% formic acid), B = Acetonitrile / gradient : 0.00-4.25 min = 20%B, 4.50min = 30%B, 19.00-22.50min = 100%B, 22.75-25.00min = 20%B) which afforded the product after drying in vacuo. The obtained amout was 130 mg (56 % of theory). LC-MS (Method 1): Rt = 1.15 min; MS (ESIpos): m/z = 518 [M+H]+

Statistics shows that 2-Methoxybenzamide is playing an increasingly important role. we look forward to future research findings about 2439-77-2.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUSS, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; (308 pag.)WO2016/173948; (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. 630-22-8, name is 2,2-Dimethylpropanethioamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 630-22-8

Example 23; N-[2-Chloro-3-(2-(1,1-dimethylethyl)-5-{2-[(2-methylpropyl)amino]-4-pyrimidinyl}-1,3-thiazol-4-yl)phenyl]-2,5-difluorobenzenesulfonamide; Step A: N-{2-Chloro-3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,5-difluorobenzenesulfonamide; To a solution of N-{2-chloro-3-[(E)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamide (3.0 g, 6.55 mmol) in DMA (25 mL) was added NBS (1.165 g, 6.55 mmol). After stirring for 1 h at rt, 2,2-dimethylpropanethioamide (0.767 g, 6.55 mmol) was added and the reaction mixture was stirred at 80 C. for 2 h. The reaction mixture was diluted with EtOAc (100 mL) and extracted five times with water. The organic layer was dried over anhydrous NaSO4, adsorbed onto silica gel, and purified via column chromatography, eluting with 0-50% EtOAc/DCM. The desired fractions were combined and concentrated to generate 1.31 g (2.36 mmol, 36.0% yield) of the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6): delta 10.74 (s, 1H), 8.56 (d, J=5.4 Hz, 1H), 7.41-7.58 (m, 6H), 6.57 (d, J=5.4 Hz, 1H), 1.42 (s, 9H). MS (ESI): 555.0 [M+H]+.

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 630-22-8.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); 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. 563-83-7, name is Isobutyramide, A new synthetic method of this compound is introduced below., Application In Synthesis of Isobutyramide

General procedure: Acetone (5.0 mL) was added to the mixture of amide (2.0 mmol) and aldehyde (1.0mmol), followed by the addition of BF3 etherate (12.6 muL, 0.1 mmol).Then the mixture was stirred at room temperature until the full consumption ofstarting material detected by TLC analysis. Then the product was collected assolid by filtration and washed with a small portion of diethyl ether. After drying under vacuum, the purity was checked by 1HNMR: only desired peaks were observed except minor solvent residue in only afew cases.

The synthetic route of 563-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yi; Zhong, Zhihao; Han, Yingmei; Han, Ruirui; Cheng, Xu; Tetrahedron; vol. 69; 52; (2013); p. 11080 – 11083;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics