Month: September 2021

Reference of 640-61-9,Some common heterocyclic compound, 640-61-9, name is N,4-Dimethylbenzenesulfonamide, molecular formula is C8H11NO2S, 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.

Prepared according to the general procedures. 1) Tube reactorwith 4 static mixers, a 6 mL reactor volume and a residencetime of 3 min, 1.5 M NaOCl (aq) at 1 mL/min and 1 MN-benzylmethylamine in EtOAc at 1 mL/min. 2) CSTR with a reactor volume of 50 mL, and residence time of 25 min. 1.1 MNaOCl (aq) at 1 mL/min and 1 M N-benzylmethylamine intoluene at 1 mL/min were used. The product was isolated foreach reactor volume by separation of the organic phase for eachreactor volume of solution and removal of the solvent by rotaryevaporation to give a white solid (1 reactor volume gives666 mg, 3.0 mmol, quantitative yield). NMR data matches thatreported in the literature [37]. 1H NMR (CDCl3, 500 MHz) deltappm 7.82 (d, J = 8.4 Hz, 2H, CHAr), 7.42 (d, J = 8.4 Hz, 2H,CHAr), 3.09 (s, 3H, NCH3), 2.48 (s, 3H, Ar-CH3); 13C NMR(CDCl3, 125 MHz) delta ppm 145.75 (CAr), 129.80 (2CHAr),129.78 (2 CHAr), 128.28 (CAr), 45.51 (NCH3), 21.70 (ArCH3).

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

Reference:
Article; Blacker, A. John; Jolley, Katherine E.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 2408 – 2417;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 7223-30-5, The chemical industry reduces the impact on the environment during synthesis 7223-30-5, name is 3-Phenylpropiolamide, I believe this compound will play a more active role in future production and life.

General procedure: A degassed solution of 3-phenylpropiolamide (5.0 mmol) and N,N-dimethylethane-1,2-diamine (5.0mmol) in DMF (6.0 mL) was added through canula to a degassed solution of thevinyl iodide (1.0 mmol), Cs2CO3 (5.0 mmol) and CuI (2.0mmol) in DMF (25.0 mL) at 23 C. After stirring for the indicated time, thereaction was quenched with water and extracted with EtOAc (x3). The combined organic layers were washedwith brine, dried over Na2SO4 and filtered. The solventwas concentrated under reduced pressure, and the residue was purified byflash chromatography as indicated.

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

Reference:
Article; Garcia-Rodriguez, Jose; Mendiratta, Saurabh; White, Michael A.; Xie, Xiao-Song; De Brabander, Jef K.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4393 – 4398;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 513-74-6, name is Ammonium carbamodithioate, 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 513-74-6, Safety of Ammonium carbamodithioate

Step 89.2: Ammonium dithiocarbamate (208 mg, 1.89 mmol) and 72 (X = Br) (200 mg, 0.63 mmol) in anhydrous MeOH (10 mL) was stirred for 10 mins. The resulting cream precipitate was collected by filtration, resuspended in acetic acid (10 mL) and refluxed for 1 hr. The reaction was cooled to room temperature and diluted with ice cold water. The resulting green precipitate was collected by filtration, redissolved in (CH2CI2:Me0H 95:5, 100 mL) and dried (Na2SO4). The pale green solution was concentrated in vacuo to give 4-(5-bromopyrazolo[1 ,5-a]pyridin-3-yl)thiazole-2(3/-/)-thione (73: X = Br) (136 mg, 70 percent) that is stored in the freezer. 1H NMR delta (400 MHz, d6-DMSO) 13.59 (br s, 1 H), 8.74 (d, J 7.3 Hz, 1H1), 8.51 ( s, 1 H ), 8.22 (d, J 1.8 Hz, 1H), 7.27 (s, 1 H1), 7.19 (dd, J 7.3, 2.1 Hz, 1 H). LCMS (APCI+) 312 (MH+ with 79Br, 100percent), 314 (MH+ with 81Br, 100percent).

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

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2009/8748; (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. 1259224-00-4, name is tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate

To the solution of 4,6-dichloro-5-iodopyrimidine (5.50 g, 20.00 mmol) (prepared according to the ref of Organic Letters; English; 11; 8; 2009; 1837 – 1840; ) in dioxane (100 mL) was slowly added the solution of tert-butyl l-(4-aminophenyl)cyclobutylcarbamate (5.2 g, 20.00 mmol) in dioxane (20 mL) and Et3N(5 ml). The reaction mixture was stirred at 80C for overnight, lc-ms indicated 4,6-dichloro-5-iodopyrimidine was completed consumed. After removed the excess solvents under the reduced pressure to get a residue, which was dissolved in Ethyl acetate (250 mL) and washed water and brine. The combined organic layer was dried over Na2S04 and then filtered, the filtrate was concentrated to give the crude product, which was further purified by flash chromatography to afford tert-butyl l-(4-(6-chloro-5-iodopyrimidin-4- ylamino)phenyl)cyclobutylcarbamate. (5.00 g 50% yield).LC/MS: (ESI+): 501 [M+l], 523 [M+Na].

The synthetic route of 1259224-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 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 127828-22-2, COA of Formula: C9H20N2O3

A solution of 6-chloro-4-hydroxy-5-methyl-3-nitropyridin-2(iH)-one (10.9 g, 53.4 mmol) in dichloromethane (380 mL) was cooled to 0 C. Triethylamine (22.3 mL, 160 mmol) was added, and the solution was stirred for ten minutes. Trifluoromethanesulfonic anhydride (18.0 mL, 107 mmol) was then added dropwise over a period of five minutes, and the solution was stirred for 1.5 hours at 0 C. A solution of tert-butyl 2-(2-aminoethoxy)ethylcarbamate (12.0 g, 58.8 mmol), prepared as described in Parts A through D of Example 102, in a small amount of dichloromethane was then added over a period of five minutes, and the reaction was allowed to warm to room temperature slowly and stirred overnight. The solution was then washed with water (2×150 mL) and brine (150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting sequentially with 80:20 hexanes:ethyl acetate and 50:50 hexanes:ethyl acetate) to provide a yellow oil, which was dissolved in diethyl ether and concentrated under reduced pressure to provide 16.5 g of trifluoromethanesulfonic acid 4-[(2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl)amino]-6-chloro-5-methyl-3-nitropyridin-2-yl ester as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Dellaria, Joseph F.; Lindstrom, Kyle J.; Dressel, Luke T.; Duffy, Daniel E.; Heppner, Philip D.; Jacobsen, John R.; Moseman, Joan T.; Moser, William H.; Radmer, Matthew R.; Stoermer, Doris; Zimmermann, Bernhard M.; US2004/10007; (2004); 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 114790-39-5 as follows. Computed Properties of C12H17NO4

A solution of benzyl N-(2,2-dimethoxyethyl)carbamate (50 g, 208.9 mmol) in toluene (180 mL) is treated with solid potassium hydroxide (51.6 g, 919.69 mmol) under nitrogen. After 10 minutes, benzyltriethylammonium chloride (0.8 g, 3.1 mmol) is added. After another 10 minutes a solution of allyl bromide (33 g, 272.8 mmol) in toluene (50 mL) is added dropwise over 10 minutes. The resultant mixture is stirred at 50 C for 48hours. The mixture is cooled to room temperature and quenched with water. The organic layer is separated, washed with brine, dried over magnesium sulfate, and concentrated to dryness to give the title compound (44 g, 75%). ES/MS (mlz): 280 (M+H).

According to the analysis of related databases, 114790-39-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; COATES, David Andrew; WOLFANGEL, Craig Daniel; (55 pag.)WO2016/122968; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, 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 389890-43-1, Application In Synthesis of tert-Butyl (cis-3-hydroxycyclobutyl)carbamate

In a round-bottomed flask charged with tert-butyl(cis-3-hydroxycyclobutyl)carbamate (1.11 g, 5.93 mmol) and triethylamine (2.474 ml, 17.79 mmol) was added CH2Cl2 (12 ml). methanesulfonyl chloride (0.505 ml, 6.52 mmol) was added dropwise via syringe at -20 C. over 5 min. The reaction mixture was stirred at room temperature for 30 min, then diluted with water (15 mL) and extracted with CH2Cl2(2*). The organic extract was washed with saturated NH4Cl and dried over MgSO4. It was filtered and concentrated in vacuo to give cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (1.64 g, 6.1 mmol, 100% yield) as a off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 42137-88-2,Some common heterocyclic compound, 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, molecular formula is C11H15Cl2NO2S, 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 (R)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-amine (2 g, 12.1 mmol) in DIPEA (4.22 mL, 24.2 mmol), N,N-bis(2-chloroethyl)-p-toluene sulfonamide (3.9 g, 13.3 mmol) was added at rt and the resulting mixture was heated to 105 C for 18 h. Completion of the reaction was confirmed by TLC. Reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layer was dried over Na2SO4 and evaporated under vacuum. To the resulting crude solid hexane (50 mL) was added, and the resulting mixture was stirred for 10 min at rt. It was filtered and the solid was washed with Et2O (2 x 50 mL) and dried under vacuum to give the title compound. Yield: 63.8% (3 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 7.59 (d, J = 8.4 Hz, 2H), 7.45 (d, J = 8.0 Hz, 2H), 6.81-6.77 (m, 2H), 6.69-6.6 (m, 1H), 5.97-5.95 (m, 2H), 3.35-3.31 (m, 1H), 2.81-2.80 (m, 4H), 2.42 (s, 3H), 2.36-2.32 (m, 4H), 1.18 (d, J= 6.8 Hz, 3H). LCMS: (Method A) 389.0 (M+H), Rt. 3.39 min, 98.9% (Max). HPLC: (Method A) Rt. 3.30 min, 99.53% (Max), Chiral HPLC: (Method A) Rt. 15.54 min, 97.58%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, its application will become more common.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, molecular formula is C13H19NO3, 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. Recommanded Product: tert-Butyl 4-(hydroxymethyl)benzylcarbamate

Stage 3 – Preparation of te/t-butyl (4-formylbenzyl)carbamate; Stage 2 product (5.87g, 24.73mmol) was stirred in DCM (20OmL) with MnO2 (16.71g, 192.2mmol) for 16h at RT. The reaction was then filtered through celite and the solvent removed in vacuo to give the product as a yellow oil (4.63g, 80%). m/z = 258 [M+Na]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123986-64-1, its application will become more common.

Reference:
Patent; CHROMA THERAPEUTICS LTD.; WO2008/40934; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 24036-52-0,Some common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, molecular formula is C8H6BrNO2, 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: Toluene (4.5mL) was added to a flask containing 6-bromo-3,4-dihydroquinolin-2(1H)-one (300mg, 1.33mmol), 3-(trifluoromethoxy)aniline (231muL, 1.73mmol), Pd2(dba)3 (15.2mg, 0.02mmol), 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (31.6mg, 0.07mmol) and NaOt-Bu (192mg, 2.00mmol) under an argon atmosphere. The mixture was stirred at 100C for 9h. After cooling, the reaction mixture was diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated in vacuo. Crude material was purified by flash chromatography with n-hexane/EtOAc (2:3) to afford the desired diaryl amine 11i

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, its application will become more common.

Reference:
Article; Takeuchi, Tomoki; Oishi, Shinya; Kaneda, Masato; Misu, Ryosuke; Ohno, Hiroaki; Sawada, Jun-Ichi; Asai, Akira; Nakamura, Shinya; Nakanishi, Isao; Fujii, Nobutaka; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3171 – 3179;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics