Month: July 2021

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 683-57-8 as follows. name: 2-Bromoacetamide

Example 1: 2-[1-(2-Morpholin-4-yl-ethoxy)-naphthalen-2-ylamino]-acetamide, hydrochloride; [Show Image] 2-Bromoacetamide (1.05 equiv), potassium carbonate (1.5 equiv) and sodium iodide (0.1 equiv) were added at r.t. to a solution of 1-(2-Morpholin-4-yl-ethoxy)-naphthalen-2-ylamine (50 mg, 0.18 mmol) in acetonitrile (3 mL). The resulting mixture was allowed to heat to 80C for 18 hours. water (10 mL) and DCM (10 mL) were added to the mixture. The organic layer was washed with water (1x) and brine (2x). After drying over MgSO4, the solvent was evaporated to afford the crude compound. This latter was purified by flash chromatography (100% EtOAc to 10% MeOH/EtOAC) to afford brown oil in 63 % yield. A 2.0 M solution of HCl in ether (10 equiv) was added to a solution of this latter in 0.5 mL of methanol to afford the HCl salt as an brown hygroscopic solid. 1H NMR (400 MHz, CD3OD) : 3.38 (s, 2H, CH2-N), 3.86 (t, J 4.9 Hz, 4H, CH2-N), 4.0-4.1 (m, 4H, CH2-O), 4.14 (s, 2H, NH-CH2-CO), 4.57 (t, J 4.8 Hz, 2H, CH2-CO), 7.31 (d, J 9.3 Hz, 1H, Ar), 7.45 (m, 1H, Ar), 7.60 (m, 1H, Ar), 7.60 (m, 1H, Ar), 7.77 (d, J 8.8 Hz, 1H, Ar), 7.90 (d, J 7.8 Hz, 1H, Ar), 8.02 (d, J 9.3 Hz, 1H, Ar). M/Z (M+H)+ = 330.

According to the analysis of related databases, 683-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Faust Pharmaceuticals; EP1777219; (2007); A1;,
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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);,
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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

Some common heterocyclic compound, 1524-40-9, name is 3-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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: C6H6FNO2S

(1) 0.0040g iridium catalyst [Cp * IrCl2] 2,0.0076 g silver salt bis(trifluoromethanesulfonyl)imide silver,0.825g oxidant silver acetate,31.4muLacetophenone-O-methyl oxime and0.07 g of m-fluorobenzenesulfonamide was placed in a reaction tube.Add 2mL of dichloromethane as a solvent,Heating and stirring reaction,The temperature of heating and stirring is 60C.Reaction time 24h.(2) After the reaction is over,Separation by column chromatography (300-400 column chromatography silica gel column packing,Eluent: ethyl acetate: petroleum ether = 12:100 v/v),Can get the product N-[2-(1-Methoxyimino)ethyl]phenyl-3-fluorobenzenesulfonamide.The yield is 83%.The structural characterization of the products are shown in Figures 21 and 22, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1524-40-9, its application will become more common.

Reference:
Patent; University of Jinan; Zhao Huaiqing; Zhang Wei; Xu Xiangwen; Wu Wei; (40 pag.)CN107739322; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 63920-73-0, 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. 63920-73-0 name is 2-Amino-4,6-dimethoxybenzamide, 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.

To a solution of 2-hydroxymethyl-benzofuran-5-carbaldehyde (0.450 g, 2.55 mmol) and 2-amino-4,6-dimethoxybenzamide (0.500 g, 2.55 mmol) in N,N-dimethylacetamide (5 mL) were added sodium hydrogen sulfite (58.5%; 0.510 g, 2.80 mmol) and p-toluenesulfonic acid (50 mg, 0.25 mmol). The reaction mixture was stirred at 120 C. for 6 hours under nitrogen and cooled to room temperature. The separated solid was filtered, washed with ether (30 mL), water (30 mL), and ethyl acetate (20 mL), and then dried under vacuum to give the title compound as a yellow solid. Yield: 0.572 g (64%). 1H NMR (400 MHz, DMSO-d6): delta 12.07 (br s, 1H), 8.44 (d, J=2.0 Hz, 1H), 8.10 (dd, J=8.8 and 1.6 Hz, 1H), 7.67 (d, J=8.8 Hz, 1H), 6.89 (s, 1H), 6.76 (d, J=2.4 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 4.61 (s, 2H), 3.90 (s, 3H), 3.86 (s, 3H). MS (ES+) m/z: 353.20 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,6-dimethoxybenzamide, and friends who are interested can also refer to it.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281398; (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, Safety 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

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, Quality Control of tert-Butyl 4-aminophenethylcarbamate

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

Reference of 2895-21-8, 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. 2895-21-8 name is N-Isopropyl-2-chloroacetamide, 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.

To a solution of /c/7-Butyl 5-(2-(3-hydroxyphenyl)-7-methoxy-6-(2- methoxyethoxy) quinazolin-4-ylamino)-1H-indazole-l -carboxylate (0.40Og, 0.72 mmol) and 2-chloro-N-isopropylacetamide (0.107g, 0.79 mmol) in DMF ( 16 mL) was added K.2CO3 (0.297g, 1.44 mmol). The mixture was heated at 80 C for 72 h. The mixture was concentrated in vacuo and taken on directly into the next step. HPLC retention time 6.76mins^

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Isopropyl-2-chloroacetamide, and friends who are interested can also refer to it.

Reference:
Patent; SURFACE LOGIX, INC.; SWEETNAM, Paul; BARTOLOZZI, Alessandra; CAMPBELL, Anthony; COLE, Bridget; FOUDOULAKIS, Hope; KIRK, Brian; SESHADRI, Hemalatha; RAM, Siya; WO2010/104851; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 119023-25-5, name is 2-Amino-4-fluorobenzamide, 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 119023-25-5, Formula: C7H7FN2O

Stage 3: 2-aminomethyl-5-fluorophenylamine 2 M borane-dimethyl sulfide complex (40 ml, 80 mmol) in tetrahydrofuran was added to a solution of the product from stage 2 (2.45 g, 16 mmol) in anhydrous tetrahydrofuran (50 ml) and the mixture was heated under reflux for 9 hours. Water (4 ml) was cautiously added to the cooled reaction solution and the mixture was then concentrated in vacuo. Toluene (2*) was added to the residue and the mixture was concentrated again each time. The residue was then repeatedly dissolved in methanol (3*) and concentrated each time. The crude product was purified by flash chromatography with chloroform/methanol (7:3) and 1% triethylamine. Yield: 1.37 g (61%), white solid. Melting point: 49-51 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-fluorobenzamide, and friends who are interested can also refer to it.

Reference:
Patent; Gruenenthal GmbH; US2008/293749; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

159790-81-5, name is (9H-Fluoren-9-yl)methyl 4-aminobenzylcarbamate, 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. Recommanded Product: 159790-81-5

N-Fmoc-para-(aminomethyl)phenylazobenzoic acid was prepared adapting literature procedures [1]. Para-nitrosobenzoic acid [2] (0.94 g, 6.2 mmol) and N-Fmoc-para-aminobenzylamine [3] (1.06 g, 3.1 mmol) were suspended in acetic acid/DMSO 1:1 (80 mL) and stirred at room temperature for 48 h. Water was added to the reaction mixture, the precipitate was filtered, washed with water several times, dried, and recrystallized from acetone/water mixtures yielding the desired azo compound (660 mg, 45%) as an orange solid.

The synthetic route of 159790-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ponader, Daniela; Igde, Sinaida; Wehle, Marko; Maerker, Katharina; Santer, Mark; Bleger, David; Hartmann, Laura; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1603 – 1612;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics