Author: tianli

121492-06-6, The chemical industry reduces the impact on the environment during synthesis 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, I believe this compound will play a more active role in future production and life.

A solution of [6-chloro-3-(1’H,3H-spiro[2-benzofuran-1,4′-piperidin]-1′-ylcarbonyl) -1H-indol-1-yl]acetic acid (prepared by treatment of the sodium salt of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidine] with bromoacetic acid at room temperature in DMF), 0-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (1.05 eq) and Et3N (1.05 eq) were stirred together at room temperature in dry DMF for 15 min. Commercially available N-(2-aminoethyl)-N-methylcarbamic acid tert-butyl ester (1.5 eq) was added and the solution stirred at room temperature for 2 h, then a solution of HCl (15 eq) in dioxane was added and the solution stirred for 2 h. Evaporation and purification by prep. HPLC gave 37% of product. ES-MS m/e (%): 481.3(M+H+).

The chemical industry reduces the impact on the environment during synthesis N-Boc-(2-Aminoethyl)-N-methylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bissantz, Caterina; Grundschober, Christophe; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2007/27173; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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. 16066-84-5.

To a suspension of sodium hydride (0.056g, 1.41 mmol) in DMF (3 mL) was added a solution of methylcarbamic acid t-butyl ester (0.184 g, 1.41 mmol) in DMF (2 mL). After stirring 1 hr, a solution of 3-(3-chloropropyl)-7-fluoro-1 -phenyl-1 H-4,2,1 – benzoxathiazine 2,2-dioxide (0.25 g, 0.72 mmol) in DMF (4 mL) was added. The mixture was stirred for 2 hr then poured into 2N HCI and extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate then concentrated and the residue purified by Sitheta2 column chromatography (10-35% gradient ethyl acetate/hexane). The purified residue was then dissolved in 5 mL of 2N HCI in ether and 0.1 mL of MeOH and the solution allowed to stand 18 hr whereupon crystals formed. The crystals were collected by filtration to yield 3-(7-fluoro-2,2-dioxido-1 – phenyl-1 H-4,2,1-benzoxathiazin-3-yl)-N-methylpropan-1 -amine hydrochloride (0.159): MS (ES) m/z 350.9;HPLC purity 100.0% at 210-370 nm, 7.4 minutes; Xterra RP18, 3.5 mu, 15O x 4.6 mm column, 1.2 mL/minutes. 85/15-5/95 (ammonium formate buffer pH =3.5/ACN+MeOH) for 10 minutes, hold 4 minutes.HRMS: calculated for Ci7H19FN2O3S + H+, 351.11732; found (ESI, [M+H]+), 351.1161.

The synthetic route of tert-Butyl methylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2008/73956; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 6292-59-7

44g (0.21 moles) of 4-tert-butyl-benzenesulfonamide, 72g (0.21 moles) of 4,6- dichloro-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidine and 0.7g of tetrabutylammonium bromide are added to a suspension of 35g (0.25 moles) of potassium carbonate in 720 ml of methyl isobutyl ketone (MIBK), kept in an inert atmosphere (nitrogen). Once the addition is complete, the suspension is heated to reflux, operating so as to azeotropically remove the water that forms during the reaction. The reaction is kept at reflux for 5 hours. Once the reaction is complete, the suspension is cooled to 5O0C and diluted with 0.2 litres of water. Hydrochloric acid 35percent is then added until obtaining a pH between 2.0 and 3.0. The suspension is cooled to 5¡ãC / 100C and the product is left to crystallise for 10 hours. The suspension is filtered and 120 g in wet form of the title compound are obtained equal to 100 g in dry form (0.19 moles) (yield 92percent; purity 99.6percent HPLC).

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIFAVITOR S.R.L.; BIFFI, Giancarlo; FELICIANI, Lazzaro; VISCARDI, Enrico; WO2010/103362; (2010); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 98-10-2, name is Benzenesulfonamide, molecular formula is C6H7NO2S, 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. 98-10-2

To a 500 ml flask was added 100 g of isopropanol,50g of benzene sulfonamide dissolved in the preparation of sodium hydroxide,Isopropanol-sodium alcohol solution (14g isopropyl alcohol dissolved in 26g isopropyl alcohol), water bath temperature, while opening the mechanical stirring,When the temperature to 50-55 C, the solid is completely dissolved, began dropping benzenesulfonyl chloride 62g, while dropping sodium hydroxide,Isopropanol-sodium alcohol solution (28g isopropyl alcohol sodium dissolved in 52g isopropyl alcohol), control system pH value of 8 to 10,Control the rate of dropping, dropping finished in 50-55 C for 2h, through the hydroxide anion exchange resin.The reaction solution was cooled to 10 C and centrifuged to obtain BBI sodium salt. The sodium salt is dissolved in hot water,Crystals were precipitated by lowering the temperature by SAPPS cation exchange resin, and the crystals were vacuum dried at 40-50 C,To obtain 84.7 g of solid bis-benzenesulfonimide. As shown in Fig. 7, the results of the HPLC detection showed: benzenesulfonamide: 0.02%;Benzenesulfonyl chloride: 0.02%; NaCl: 0.08%; BBI: 99.96%; Yield: 89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98-10-2, its application will become more common.

Reference:
Patent; Hubei Kyrgyzstan and Chang Chemical Technology Co., Ltd; Xiao, Zhongxin; Feng, Qingcheng; Yang, Wei; Zhou, Shijun; Ming, Ruitao; Guo, Xinyue; Hu, Zhe; Huang, Kaiwei; (8 pag.)CN106187831; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

3144-09-0, These common heterocyclic compound, 3144-09-0, name is Methylsulfonamide, 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.

Add in the reaction flask2- (4 – ((5,6-diphenylpyrazin-2-yl) (isopropyl) amino) butoxy) acetic acid (S-I)(21.0 g, 0.05 mol), carbonyldiimidazole (12.2 g, 0.075 mol) andDichloromethane (210 mL), heated to reflux for 1 hour,The temperature was lowered to 20-30 C, methanesulfonamide (9.5 g, 0.10 mol)After stirring for 10 minutes, triethylamine (10.1 g, 0.10 mol)Continue to react for 5 hours. Water (50 mL) was added,Dropping 1N hydrochloric acid to adjust the pH of the system to 5-6, liquid separation,The organic phase was washed with water (50 mL ¡Á 2), dried over anhydrous sodium sulfate,Filtration, the filtrate was concentrated under reduced pressure Sai Xip crude(Purity: 99.16%, HPLC chromatogram shown in Figure 1),The crude product was recrystallized from absolute ethanol (270 mL) to give a white solid racemic solution(24.0 g, yield: 96.8%, purity: 99.93%,HPLC chromatogram shown in Figure 2).

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 3144-09-0.

Reference:
Patent; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Zhang Qianqian; Qu Xiaoxia; (14 pag.)CN107365275; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1882-71-9, 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. 1882-71-9, name is 2-Amino-5-methoxybenzamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a cold (0-5 ¡ãC) stirred suspension of aminobenzamides 2a-g (0.016 mol) in pyridine (13 ml), 0.016 mol of the appropriate cinnamoyl chloride 3a-e, 3-phenylpropioloyl chloride 3f-k and 3-phenylpropanoyl chloride 3l-o was added over 30 min. After addition was complete, the solution was stirred for 24 h and then poured onto crushed ice. The precipitate was removed by filtration, washed with water, and crystallized from the appropriate solvent.

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:
Article; Raffa, Demetrio; Maggio, Benedetta; Raimondi, Maria Valeria; Cusimano, Maria Grazia; Amico, Giandomenico; Carollo, Anna; Conaldi, Pier Giulio; Bai, Ruoli; Hamel, Ernest; Daidone, Giuseppe; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 427 – 435;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, 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. 1103234-56-5

Example 1; Step a; Formation of Carboxylic Acid Chloride (Step a) 1) According to Scheme 1); 55.8 g Sulfonamide Acid (2) was placed into a dried 1st reaction vessel kept under nitrogen atmosphere, to which 280 mL methylenchloride were added. Then 619 muL DMF were added to the obtained suspension and the resulting mixture was kept at a temperature between 18-22 C. Then, 25.4 g oxalylchloride were dissolved in 66 mL methylenchloride, and this solution was slowly added over approximately 30 minutes to the above-mentioned suspension whereby the temperature of said suspension was kept between 18-22 C. The formation of CO2 and CO could be observed during said addition. The reaction mixture was then further stirred for about 4 to 6 hours and further kept at a temperature between 18-22 C. until the suspension almost entirely turned into a solution and no gas formation could be observed any more.

Statistics shows that 1103234-56-5 is playing an increasingly important role. we look forward to future research findings about 2,6-Difluoro-3-(propylsulfonamido)benzoic acid.

Reference:
Patent; Hildbrand, Stefan; Mair, Hans-Juergen; Radinov, Roumen Nikolaev; Ren, Yi; Wright, James Anderson; US2011/28511; (2011); 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. 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., 1103234-56-5

3H-Imidazo[4,5-b]pyridin-6-amine (29 mg, 0.22 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (60 mg, 0.22 mmol, 1 eq.), EDCI (46 mg, 0.24 mmol, 1.1 eq.), and 1-hydroxybenzotriazole (“HOBT”)eta2O (33 mg, 0.22 mmol, 1 eq.) were combined in dry DMF (2 mL) and stirred at room temperature for 16 hours. The reaction mixture was then diluted with brine and extracted with ethyl acetate (“EtOAc”; 2 X). The extracts were washed with water (1 X), dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by preparative TLC (2 X 0.5 mm plates, 10% MeOH/DCM) to give 2,6-difluoro-N-(3H-imidazo[4,5-b]pyridin-6-yl)-3-(propylsulfonamido)benzamide (7.4 mg, 9%). 1H NMR (400 MHz, DMSOd6) delta 12.63 (br s, IH), 11.03 (br s, IH), 9.81 (br s, IH), 8.43-8.53 (m, 3H), 7.53-7.59 (m, IH), 7.26-7.30 (m, IH), 3.11-3.15 (m, 2H), 1.74-1.80 (m, 2H), 0.98-1.02 (m, 3H); m/z (APCI-pos) M+l = 394.3.

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; ARRAY BIOPHARMA INC.; GENENTECH, INC.; WO2009/111277; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6269-91-6, 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. 6269-91-6 name is 2-Methyl-5-nitrobenzenesulfonamide, 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 stirred solution of 2-methyl-5-nitrobenzenesulfonamide (4.6 g, 0.021 mol) in 2-methoxyethyl ether (43 mL), at 0¡ã C., was added a solution of 16.1 g of tin(II) chloride in 32 mL of concentrated HCl dropwise over 15 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 130 mL of diethyl ether was added to reaction. The mixture was stirred vigorously for 1 h. The mixture was basified with a solution of NaOH and NaHCO3, and extracted with ethyl acetate (*3). The combined ethyl acetate layers were dried over anhydrous MgSO4, filtered and concentrated to give crude product. Trituation of the crude product with methanol provided 2.4 g of pure 5-amino-2-methylbenzenesulfonamide as light brown solid. 1H NMR (300 MHz, DMSO-d6) delta 7.11-7.10 (m, 3H), 6.95 (d, J=8.1 Hz, 1H), 6.60 (dd, J=8.1 and 2.4 Hz, 1H), 5.24 (s, 2H), 2.36 (s, 3H). MS (ES+, m/z) 187 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-5-nitrobenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; US2008/293691; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 711007-44-2, name is 2,3-Diaminobenzamide, 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 711007-44-2. 711007-44-2

2: To a solution of 2-(tert-butoxycarbonyl)-7-((tert-butoxycarbonyl)amino)- l,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (200 mg, 0.51 mmol) in anhydrous DMF (3 mL) was added EDCHCl (293 mg, 1.53 mmol), HOAt (105 mg, 0.77 mmol) and triethylamine (0.107 ml, 0.77 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3-diaminobenzamide (77 mg, 0.51 mmol) was added and heated to 800C over night. The reaction mixture was concentrated and purified by preparative TLC to afford tert-butyl 3-((2- amino-3-carbamoylphenyl)carbamoyl)-7-((tert-butoxycarbonyl)amino)-3,4-dihydroisoquinoline- 2(lH)-carboxylate. MS (ES+): m/z 526.30 [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 2,3-Diaminobenzamide.

Reference:
Patent; ANGION BIOMEDICA CORP.; PANICKER, Bijoy; LIM, Dong, Sung; SMITH, David, E.; WO2011/2520; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics