Month: September 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 118684-31-4 as follows. name: tert-Butyl (3-(hydroxymethyl)phenyl)carbamate

[3-(2′,4′-Difluoro-biphenyl-4-yloxymethyl)-phenyl]-carbamic acid tert-butyl esterTo 10 mL of dry CH2Cl2 under argon, in an ice bath, was added 2′,4′-difluoro-biphenyl-4-ol (206 mg, 1.0 mmol) and triphenylphosphine resin (1.1 meq/g, 1.36 g, 1.5 mmol). The mixture was stirred for 20 min and DIAD (295 uL, 1.5 mmol) was added. The reaction was stirred an additional 5 min at ice bath temperature and [3-(2′,4′-difluoro-biphenyl-4-yloxymethyl)-phenyl]-carbamic acid tert-butyl ester (223 mg, 1.0 mmol) and triethylamine (209 uL, 1.5 mmol) were added. The mixture was stirred at ice bath temperature for 20 min and allowed to warm slowly to RT and stirred overnight. The reaction mixture was filtered, concentrated and purified by flash chromatography with a gradient of 0-10% ethyl acetate in hexanes to yield 235.4 mg (57%) of [3-(2′,4′-difluoro-biphenyl-4-yloxymethyl)-phenyl]-carbamic acid tert-butyl ester. 1H-NMR (CDCl3) delta ppm 1.52 (s, 2H), 6.51 (br. S, 1H), 6.82-6.98 (m, 2H), 7.03 (d, J=8.7 Hz, 2H), 7.08-7.17 (m, 1H), 7.28-7.39 (m, 3H), 7.42 (d, j=8.7 Hz, 2H), 7.50 (s, 1H).

According to the analysis of related databases, 118684-31-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US7939569; (2011); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 25216-74-4, 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. 25216-74-4, name is tert-Butyl (3-bromophenyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (4.3 g) and N-tert-butoxycarbonyl-3-bromoaniline (3.79 g) was cooled to -78 C. To the solution was gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (42 ml). To the mixture were added water (100 ml) and acetic acid ethyl ester (300 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The _solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-amino-3′-tert-butoxycarbonylamino-5-chlorobenzophenone (0.7 g) as a yellow oily product.

The synthetic route of tert-Butyl (3-bromophenyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6352982; (2002); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, 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 85006-25-3, Computed Properties of C10H19NO5

Commercially available Compound 12 (6.7 g, 28.7 mmol), 2-methoxyethanol (2.267 mL, 28.7 mmol) and triphenylphosphine(9 g, 34.5 mmol) were dissolved in tetrahydrofuran (67 mL) under water-cooling bath, and 2.2 mol/L DEADtoluenesolution (15.67 mL, 34.5 mmol) was added dropwise to the solution over 30 minutes. Then, the reaction mixturewas stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silicagel column chromatography (hexane-ethyl acetate) to give Compound 13 (8.15 g, Yield 97.4%).LC/MS (Method 2) RT = 2.20, MS (m/z) = 292

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; Shionogi & Co., Ltd.; YUKIMASA, Akira; NAKAMURA, Kenichiroh; INAGAKI, Masanao; KANO, Kazuya; FUJIU, Motohiro; YAMAGUCHI, Hiroki; HATA, Kayoko; INOUE, Takatsugu; (253 pag.)EP3330256; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 24566-95-8, 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 24566-95-8 as follows.

General procedure: p-Chloro-N-alkylbenzenesulfonamides (1-8) (1 equiv.) andaminolactam N-(3-aminopropyl)-2-pyrrolidinone (APP)(1.25 equiv.) or N-(3-aminopropyl)-2-azepanone (APA)(1.25 equiv.) were added to a 50 mL round-bottomed flaskand dissolved in dimethylsulfoxide (10 mL) for a nucleophilicaromatic substitution reaction (SNAr). The contents were then stirred in a reflux system for 1-2 h at 85 C.Afterward, the solvent was removed with frozen water andthe product was treated with diluted HCl (5 %) for removalof amino-lactam excess. The crude product was filtered offand recrystallized from 1:1 ethyl ether-petroleum ether (bp60-80 C). All obtained compounds were structurally confirmedby 13C and 1H NMR analyses (see Supplementarymaterial).

According to the analysis of related databases, 24566-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Martins, Carina C.; Bassetto, Carlos A. Zanutto; Santos, Jandyson M.; Eberlin, Marcos N.; Magalhaes, Alvicler; Varanda, Wamberto; Gonzalez, Eduardo R. Perez; Amino Acids; vol. 48; 2; (2016); p. 445 – 459;,
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. 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H12N2O

6.19. Preparation of l-(4-(4-(2-nnet yl-5-((2S.3R.4R.5S.6R)-3.4.5-tririvdroxy-6- (met yltriio)tetra vdro-2H-pyran-2- yl)benzyl)prienoxy)butanannido)cvclopentanecarboxamide (41) 4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2- yl)benzyl)phenoxy)butanoic acid (39, 46 mg, 0.10 mmol), 1-aminocyclopentanecarboxamide (26 mg, 0.20 mmol), HATU (57 mg, 0.15 mmol), and DIPEA (52 muIota_, 0.30 mmol) were combined in DMF (0.5 ml_) and stirred overnight at room temperature. The reaction was diluted with EtOAc, washed with saturated aqueous NaHC03 and brine (with back extraction), dried over MgS04, filtered, and concentrated under vacuum. The material was purified by prep HPLC (C18 30 x 100 mm column, 20-60% CH3CN /10 mM aqueous ammonium formate, 45 mL/min) and lyophilized to give 35 mg (61% yield) of amide 41 as a white solid. W NMR (400 MHz, MeOH-d4) delta ppm 7.10 – 7.19 (m, 3 H), 7.04 (d, J=8.6 Hz, 2 H), 6.81 (m, J=8.6 Hz, 2 H), 4.39 (d, J=9.3 Hz, 1 H), 4.12 (d, J=9.1 Hz, 1 H), 3.96 (t, J=6.2 Hz, 2 H), 3.92 (s, 2 H), 3.34 – 3.50 (m, 3 H), 2.41 (t, J=7.5 Hz, 2 H), 2.12 – 2.22 (m, 8 H), 2.04 (quin, J=6.9 Hz, 2 H), 1.93 (dt, J=12.8, 5.1 Hz, 2 H), 1.64 – 1.75 (m, 4 H); MS (ES+) [M+H]+ = 573.

According to the analysis of related databases, 17193-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; CARSON, Kenneth Gordon; GOODWIN, Nicole Cathleen; HARRISON, Bryce Alden; RAWLINS, David Brent; STROBEL, Eric; ZAMBROWICZ, Brian; WO2014/81660; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 56987-35-0, name is 3,3-Dibromo-azepan-2-one, 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 56987-35-0, name: 3,3-Dibromo-azepan-2-one

11.3 g of the caprolactam was dissolved in 200 ml of methylene chloride,41.6 g of phosphorus pentachloride was added portionwise under ice-cooling, and the reaction was continued for 10 minutes after the completion of the addition. 1 g of zinc iodide was added under a nitrogen atmosphere,The reaction was allowed to proceed to room temperature for 1 hour. A solution of bromine in dichloromethane (32 g of bromine in 100 ml of dichloromethane) was then added dropwise,After completion of the addition, the mixture was stirred overnight. The ice bath was cooled to 0 to 5 degrees,The reaction was carefully poured into 500 ml of ice water,Extracted with dichloromethane for 5 times,Dried over anhydrous sodium sulfate,After concentration, a mixed solvent of petroleum ether and ethyl acetate was added,Precipitation of solid,Filtration gave 23 g of solid,Directly used in the next step reaction. 13.5 g of 3,3-dibromoheptalactam was dissolved in 70 ml of dry DMF,4 g of lithium chloride were added successively,7 grams of lithium carbonate,After heating to 130 C for 8 hours,DMF was distilled off,Purification by column afforded 7.1 g of a white solid,Yield 75%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,3-Dibromo-azepan-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Second Military Medical University,People’s Liberation Army; Miao, Zhen Yuan; Zhang, Wannian; Wu, yue Lin; Sheng, chun Quan; Zhuang, Chunlin; Xiao, Min; Yao, Jianzhong; Dong, Guoqiang; (40 pag.)CN105367495; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 758-96-3, The chemical industry reduces the impact on the environment during synthesis 758-96-3, name is N,N-Dimethylpropionamide, I believe this compound will play a more active role in future production and life.

General procedure: tert-Butyl acetate (0.14 mL; 1.0 mmol) was added to a solution of LDA (1.0 mmol) in 3 mL of dry THF at -78 C under argon atmosphere with stirring. After the solution was stirred for 10 min, a solution of vinyl sulfoxide 8 (71 mg; 0.2 mmol) in THF (1 mL) was added. The reaction mixture was stirred for 15 min and then reaction was quenched by adding saturated aq. NH4Cl. The whole mixture was extracted with CHCl3. The product was purified by silica gel column chromatography to afford adduct 9 (94 mg; 99%) as colorless oil.

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

Reference:
Article; Satoh, Tsuyoshi; Awata, Yu; Kato, Yuichi; Ogata, Shingo; Ishigaki, Masashi; Sugiyama, Shimpei; Saitoh, Hideki; Tetrahedron; vol. 67; 6; (2011); p. 1102 – 1113;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 143557-91-9,Some common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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.

3alpha-Cyclopropylmethoxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester A reaction flask was charged with crude 3alpha-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester (5.5 g) in dry DMF (25 mL) under Argon. NaH (60% in oil, 0.968 g, 24.2 mmol) was added in portions and the mixture was stirred at 50 for 1 h. The mixture was cooled to rt and bromomethylcyclopropane (3.252 g, 24.2 mmol) was added followed by stirring at rt for 20 h under Argon. The reaction mixture was quenched with water and the product extracted into EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (3.354 g). 1H NMR (CDCl3) delta 3.98-3.94 (m, 2H), 3.44-3.40 (m, 1H), 3.05 (d, 2H), 1.96-1.88 (m, 2H), 1.79-1.62 (m, 6H), 1.29 (s, 9H), 0.88-0.79 (m, 1H), 0.35-0.30 (m, 2H), 0.04-0.00 (m, 2H); 13C NMR (CDCl3) delta 153.4, 78.9, 73.0, 72.5, 52.7, 34.9, 28.5, 28.1, 10.9, 2.8.

The synthetic route of 143557-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACADIA PHARMACEUTICALS, INC.; Skjaerbaek, Niels; Koch, Kristian Norup; Friberg, Bo Lennart Mikael; Tolf, Bo-Ragnar; (70 pag.)US9522906; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37045-73-1, name is 3-(Methylsulfonamido)aniline, 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 37045-73-1, Quality Control of 3-(Methylsulfonamido)aniline

This was prepared from 2,4-dichloro-5-methylpyrimidine (0.326 g), N-(3- aminophenyl)methanesulfonamide (0.372 g) and DIPEA (0.418 mL) using procedure B (reaction time, 48 h) and isolated in the same way as MA2-030 to give the title compound MA2-035 as a gray solid (0.374 g, 100%). Mp: 191-193 C. NMR (400 MHz, DMSO-ifc): delta 9.85 (s, 1H, disappeared on D2O shake), 8.95 (s, 1H, disappeared on D2O shake), 8.06 (d, / = 0.9 Hz, 1H), 7.54 (t, / = 1.9 Hz, 1H), 7.35 (dd, / = 8.4, 1.5 Hz, 1H), 7.30 (t, / = 8.0 Hz, 1H), 6.91 (ddd, / = 7.8, 2.0, 1.1 Hz, 1H), 3.05 (s, 3H), 2.17 (s, 3H). HPLC-MS (ESI+): m/z 315.2 [40%, (M35C137 +], 313.1 [100%, (M35C135C1+H)+]. Procedure B A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

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; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 14719-21-2, The chemical industry reduces the impact on the environment during synthesis 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, I believe this compound will play a more active role in future production and life.

A solution of compound 57 (50 mg, 0.08 mmol), N-propargyltrifluoroacetylamide (117 mg, 0.8 mmol), tetrakis(triphenylphosphine)-palladium(0) (18 mg, 0.02 mmol), Cul (5.9 mg, 0.03 mmol), and Et3N (48 mu?, 0.34 mmol) in anhydrous DMF (3.0 mL) was stirred at 50 C for 12 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography to yield 7-{(5)-l-[5-methoxy-4-(3-trifluoroacetamido-l-propynyl)-2-nitrophenyl]-2,2-dimethyl-propyloxy}methyl-7-deaza-2′-deoxyguanosine 58 (50 mg, 96%). 1H NMR (400 MHz, MeOH-d4): delta 7.87 (s, 1 H, Ph-H), 7.26 (s, 1 H, Ph-H), 6.84 (s, 1 H, H-8), 6.20 (m, 1 H, H-l ‘), 5.25 (s, 1 H, Ph-CH), 4.67 (d, 1 H, J = 12.0 Hz, 7-CH2a), 4.54 (d, 1 H, J = 12.0 Hz, 7-CH2b), 4.43 (m, 1 H, H-3 ‘), 4.33 (s, 2 H, CH2), 3.95 (s, 3 H, OCH3), 3.89 (m, 1 H, H-4′), 3.70 (m, 2 H, H-5’), 2.46 (m, 1 H, H-2’a), 2.18 (m, 1 H, H-2’b), 0.86 (s, 9 H, (CH3)3).

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, 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics