Month: September 2021

2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 2675-89-0

To a stirred mixture of 8-piperidin-4-yl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid (2-hydroxy-ethyl)-isopropyl-amide hydrochloride (127 mg, 0.23 mmol) in DMF (2 mL) was added potassium carbonate (127 mg, 0.92 mmol), N,N-dimethyl-2-chloroacetamide (36 mg, 0.3 mmol) and KI (catalytic) and stirring continued at RT for 72 h before concentrating in vacuo. The resultant residue was diluted with ethyl acetate and washed with water followed by brine, then dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was passed down an Isolute SCX-2 cartridge eluting with DCM/methanol then 2M NH3 in methanol. Basic fractions were combined and concentrated in vacuo, the residue subjected to RPHPLC (C18 column, gradient 5 to 95% CH3CN in water+0.1% HCO2H) to give 356 as a colourless glass (22 mg, 20%). LCMS: RT=1.90 min, [M+H]+=484 1H NMR 400 MHz (CDCl3) delta: 8.42 (2H, s), 8.20 (1H, br, s), 8.34 (1H, d, J=8.32 Hz), 7.81 (1H, s), 7.04 (1H, dd, J=8.40, 1.77 Hz), 6.90 (1H, d, J=1.69 Hz), 4.63 (2H, m), 4.45-4.44 (4H, m), 3.38 (3H, m), 3.32 (2H, m), 3.16 (2H, d, J=11.21 Hz), 3.11 (3H, s), 2.99 (3H, s), 2.56 (1H, m), 2.48 (2H, m), 1.87 (4H, m), 1.42 (6H, d, J=6.46 Hz)

The synthetic route of 2675-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blaquiere, Nicole; Do, Steven; Dudley, Danette; Folkes, Adrian; Heald, Robert; Heffron, Timothy; Jones, Mark; Kolesnikov, Aleksandr; Ndubaku, Chudi; Olivero, Alan G.; Price, Stephen; Staben, Steven; Wang, Lan; US2011/76292; (2011); 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 142-26-7 as follows. Computed Properties of C4H9NO2

To a solution of 4-((2′, 3, 3′, 5-tetrafluoro-5′ -(anti-3-methoxycyclobutoxy)-[1, 1′-biphenyl]-4-yl)oxy)butanoic acid (56 mg, 0.13 mmol) in dry DCM (0.6 mL) was added thionyl chloride (19 muL, 0.26 mmol) at 0 C, stirred at 55 C for 8h. The reaction solvent was removed under reduced pressure. The crude product was dissolved in dry DCM (0.6 mL). The mixture was added N-(2-hydroxyethyl) acetamide (12 muL, 0.13 mmol), then was stirred at r.t. for 0.5-1h. Add triethylamine (46 muL, 0.065 mmol) to the reaction mixture stirred at r.t. for 3h. The reaction solvent was removed under reduced pressure to afford crude product. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 1 : 1 as eluent) to give 4-((2′, 3,3′,5-tetrafluoro-5′-(anti-3-methoxycyclobutoxy)-[1,1′-biphenyl]-4-yl)oxy)butanoate (18 mg, 27% yield) as colorless oil. 1H NMR (300 MHz, CDCl3) delta 7.16-6.99 (m, 2H), 6.65-6.56 (m, 1H), 6.54-6.51 (m, 1H), 5.86 (s, 1H), 4.83-4.76 (m, 1H), 4.29-4.15 (m, 4H), 4.15-4.07 (m, 1H), 3.54 (dd, J = 10.5 Hz, J = 5.5 Hz, 2H), 3.28 (s, 3H), 2.64 (t, J = 7.2 Hz, 2H), 2.51-2.36 (m, 4H), 2.17-2.07 (m, 2H), 2.00 (s, 3H); HRMS (ESI): Exact mass calcd. for C25H27F4NO6Na [M+Na] + 536.1672 found 536.16667.

According to the analysis of related databases, 142-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sheng, Ren; Yang, Liu; Zhang, Yanchun; Xing, Enming; Shi, Rui; Wen, Xiaoan; Wang, Heyao; Sun, Hongbin; Bioorganic and Medicinal Chemistry Letters; vol. 28; 15; (2018); p. 2599 – 2604;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 3144-09-0,Some common heterocyclic compound, 3144-09-0, name is Methylsulfonamide, molecular formula is CH5NO2S, 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.

Methane sulfonamide (10 gm) and n-butylacetate (80 mL) were charged into a 250 mL round bottom flask at 30C. Chloroacetylchloride (21 .37 gm) was added slowly over a period of 10 minutes at 30C. Temperature of the reaction mass was raised to 125C and maintained reflux for 16 hours. Progress of the reaction was monitored by TLC and after completion of the reaction the mass was cooled to 20C and stirred for 1 hour at 20C. Reaction mass was filtered and the wet solid was washed with n- butylacetate (10 mL). The wet solid was taken into another 100 mL round bottom flask and n-butylacetate (50 mL) was added and stirred for 30 minutes at 20C. The precipitation was filtered and the solid was suck dried. The material was dried at 45 under vacuum for 5 hours to yield 14 gm of title compound.

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

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; DAHANUKAR, Vilas Hareshwar; CHINTADA, Krishnarao; SHAIKH, Latif Jafar; YARRAGUNTLA, Sesha Reddy; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; (33 pag.)WO2017/29594; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 5004-88-6,Some common heterocyclic compound, 5004-88-6, name is 2-Amino-4,5-dimethoxybenzamide, molecular formula is C9H12N2O3, 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.

Example 50 2-(4-(6,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)acetamide A solution of 4-hydroxy-3,5-dimethoxybenzaldehyde (1.0 g, 6.66 mmol) in DMF (10 mL) was cooled to 0 C. under nitrogen. NaH (0.4 g, 10 mmol, 60% in oil) was added portion-wise. The reaction was stirred for 30 min, then 2-bromoacetamide (0.918 g, 6.66 mmol) was added and stirring was continued for 36 h at room temperature. The DMF was removed under reduced pressure and water (50 mL) was added. The mixture was extracted with EtOAc (50 mL*3). The combined organic layers were washed with an aqueous solution of NaOH (50 mL, 10%), washed with water (50 mL) and brine solution (50 mL) and dried over MgSO4 and concentrated to give 0.6 g of crude intermediate, which was purified by flash column chromatography to provide the desired intermediate (366 mg, 26%), as a white solid. A mixture of 2-amino-4,5-dimethoxybenzamide (0.2 g, 1.019 mmol), 2-(4-formyl-2,6-dimethyl-phenoxy acetamide (0.211 g, 1.019 mmol), sodium hydrogensulfite (0.116 g, 1.121 mmol) and p-toluenesulfonic acid (20 mg) in N,N-dimethyl acetamide (5 mL) was stirred at 150 C. for 16 h under nitrogen. The reaction mixture was cooled to room temperature and water (50 mL) was added. The white precipitate was filtered off and washed with cold water (30 mL*2) and dried under high vacuum to provide 2-(4-(6,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)acetamide (300 mg, 76%) as a off white solid. Selected data: MS (ES) m/z: 384.1 (M+1); MP 354-356 C.

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-4,5-dimethoxybenzamide, its application will become more common.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter Ronald; US2013/281397; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 13304-62-6,Some common heterocyclic compound, 13304-62-6, name is N-Benzylacrylamide, molecular formula is C10H11NO, 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: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.

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

Reference:
Article; Zhang, Yikai; Lv, Zhiliang; Zhong, Hanyu; Zhang, Mingfeng; Zhang, Tao; Zhang, Wannian; Li, Ke; Tetrahedron; vol. 68; 47; (2012); p. 9777 – 9787;,
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 120157-97-3 as follows. category: amides-buliding-blocks

Under nitrogen, compound X (from Example 38 part a) (5.0 g, 16.7 mmol) was mixed with toluene (80 mL) and 4-methoxy-3-phenylaniline hydrochloride (4.3 g, 18.3 mmol) was added to form a slurry. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (1.6 g, 2.5 mmol) was added, followed by tris(dibenzylideneacetone)dipalladium(0) (760 mg, 0.83 mmol) and finally sodium tert-butoxide (5.3 g, 55 mmol). The mixture was heated at 90 C. for 150 min and then cooled to room temperature. Water (150 mL) was added followed by ethyl acetate (150 mL) and the phases partitioned. The aqueous layer was extracted with ethyl acetate (150 mL) and the combined organics washed three times with 0.5 M sodium bisulfate (200 mL), once with saturated sodium bicarbonate (150 mL) and twice with saturated sodium chloride (150 mL). The organics were dried over magnesium sulfate (50 g) and the volatiles removed under vacuum to give N-tert-butoxycarbonyl-2-[4-(3-[phenyl-4-methoxyphenyl)aminophenyl]ethylamine (LL) (8.4 g) which was used without further purification.

According to the analysis of related databases, 120157-97-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 6973-09-7,Some common heterocyclic compound, 6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, molecular formula is C7H10N2O2S, 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 mixture of 5-amino-2-methylbenzenesulfonamide (14.4 mg, 0.077 mmol) and compound 13a (20 mg, 0.077 mmol) in 1-butanol (1.5 mL) was subjected to ultrasonic reaction at 200 ° C for 30 minutes. The reaction vial was cooled to room temperature and the solvent was evaporated under vacuum. The crude product was purified by flash column chromatography (MeOH: DCM = 1: 20) to give compound MKP101 (20.1 mg, 0.0492 mmol, 63.9percent).

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

Reference:
Patent; CHUNG ANG University industry Academic Cooperation Foundation; Min, Kyung-Hoon; (30 pag.)KR2016/147170; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 127828-22-2, 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 127828-22-2 as follows.

(1) 20 g of tert-butyl terminal amino-terminated diethylene glycol carbamate was added to 100 ml of saturated sodium bicarbonate, 13.8 g of N-methoxycarbonyl maleimide was weighed and added slowly at 0C. The above solution was stirred for 2 h. TLC showed the reaction was complete and ethyl acetate was extracted 3 times. The ethyl acetate phase was dried over anhydrous sodium sulfate, spin-dried, and purified by column to obtain 22 g of a product. Yield: 90%

According to the analysis of related databases, 127828-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Deng Zeping; Cheng Jia; Zhang Anlin; Li Hu; (12 pag.)CN107501378; (2017); A;,
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. 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-N-cyclopropylacetamide

General procedure: The appropriate 1,2,4-triazole-3-thiol (45-69, 1 equiv), 2-chloro-acetamide (70a-m, 1.1 equiv), Cs2CO3 (1.1 equiv) and NaI (0.05 equiv) were stirred in dry MeCN at 50C, and reaction progress was monitored by UPLC/MS. Then water was added, and the final compounds 3-42 were purified by washing the precipitated powder or by flash chromatography (Scheme 1).

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 19047-31-5.

Reference:
Article; Roberti, Marinella; Schipani, Fabrizio; Bagnolini, Greta; Milano, Domenico; Giacomini, Elisa; Falchi, Federico; Balboni, Andrea; Manerba, Marcella; Farabegoli, Fulvia; De Franco, Francesca; Robertson, Janet; Minucci, Saverio; Pallavicini, Isabella; Di Stefano, Giuseppina; Girotto, Stefania; Pellicciari, Roberto; Cavalli, Andrea; European Journal of Medicinal Chemistry; vol. 165; (2019); p. 80 – 92;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 146651-75-4, 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. 146651-75-4 name is tert-Butyl (2-aminophenyl)carbamate, 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.

Reference Example 2 N-(2-t-Butoxycarbonylaminophenyl)-5-methoxycarbonylpyridine-2-carboxylic acid amide (Reference Compound No.2-1) HATU (21 g, 55 mmol) was added to a solution of 2-aminophenylcarbamic acid t-butyl ester (Reference Compound No.1-1, 10 g, 50 mmol), 5-methoxycarbonylpyridine-2-carboxylic acid (10 g, 55 mmol), and N-methylmorpholine (11 mL, 100 mmol) in DMF (100 mL), and then the reaction mixture was stirred at room temperature for 20 hours. Water (300 mL) was added thereto, and then the whole was extracted with ethyl acetate (300 mL) three times. The organic layer was washed with brine (200 mL), and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the obtained solid was collected by filtration to give 15 g of the title reference compound as a pale brown solid. (Yield 79%)

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

Reference:
Patent; Santen Pharmaceutical Co., Ltd; EP2135620; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics