Month: July 2021

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, category: amides-buliding-blocks

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

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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H17NO3

(1-((4-(3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fl uorophenoxy)methyl)cyclopropyl)carbamate 2-Chloro-4-(3-(3-fluoro-4-hydroxyphenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolid in-1-yl)benzonitrile 35c (100 mg, 0.26 mmol) was dissolved in 5 mL of methylbenzene, followed by addition of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate 6a (49 mg, 0.26 mmol), 1,1′-(azodicarbonyl)dipiperidine (106 mg, 0.42 mmol) and tri-n-butylphosphine (85 mg, 0.42 mmol) successively. The reaction solution was warmed up to 50C and stirred for 2 hours. The resulting solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system B to obtain the title compound tert-butyl (1-((4-(3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fl uorophenoxy)methyl)cyclopropyl)carbamate 35d (80 mg, yield 55.9%) as a white solid.

According to the analysis of related databases, 107017-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; Jiangsu Hengrui Medicine Co. Ltd.; LU, Hejun; SUN, Piaoyang; FEI, Hongbo; JIANG, Hongjian; WANG, Haowei; DONG, Qing; EP2894151; (2015); 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 118684-31-4 as follows. Recommanded Product: 118684-31-4

[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

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., HPLC 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

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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl (2-hydroxyethyl)(methyl)carbamate

Reference Synthetic Example 14 Ethyl 2-(methylamino)ethyl carbonate hydrochloride To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and ethyl chlorocarbonate (1.25 mL) was added. After stirring overnight at room temperature, ethyl acetate (50 mL) was added to the reaction solution, and washed sequentially with water (50 mL), 5% aqueous solution of citric acid (50 mL), and saturated saline (50 mL), followed by drying over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and to the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 2 hrs, diethyl ether (10 mL) was added thereto, and the depositting solid was collected by filtration. The solid was dried under reduced pressure to give title compound as white solid (1.66 g). 1H-NMR (DMSO-d6): 1.23 (3H,t,J=7.1Hz), 2.54(3H,s), 3.16-3.22(2H,m), 4.15 (2H,q,J=7.1Hz), 4.32-4.37(2H,m), 9.25(2H,br).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1602362; (2005); A1;,
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, HPLC of Formula: C7H10N2O2S

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

Related Products of 67442-07-3, These common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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.

1L three bottles of iodine was added 20g2–chloro-7-fluoro-9,9-fluorene and 500mLTHF, clear solution. Temperature of the system was cooled to -10 deg.] C, was added dropwise 41g18percent of isopropylmagnesium chloride in tetrahydrofuran was incubated for 1 hour. Then a solution of toluene solution 54g20percent of active amide. Incubated for 1 hour. End of the reaction, with 40g15percent hydrochloric acid quenched stratification. Toluene and the combined organic phases. Removing solvent gave the crude product was recrystallized from toluene to give 2-chloro-1- (7-chloro-9,9-difluoro-9H-fluoren-2-yl) ethanone15g, a yield of 86.8percent.

The synthetic route of 67442-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Wansu Chemicals Co., Ltd; Xu, Zhi; Wang, Shaobo; Sun, Zhongyue; Du, Weiping; (19 pag.)CN105237384; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1520-70-3, name is Ethanesulfonamide, 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. category: amides-buliding-blocks

A solution (0.05 M) of 3-cyclohexyl-1-[2(dimethylamino)-2-oxoethyl]-2-phenyl-1H- INDOLE-6-CARBOXYLIC acid (from Example 7) in CH2C12 was treated with DMAP (1.5 EQ.) and ethane sulfonamide (1.5 eq. ). EDCI (1.5 eq. ) was added and the mixture was stirred overnight. The volatiles were evaporated under reduced pressure and the residue was purified by RP-HPLC to afford the title compound (42 percent) as a solid. 1H NMR (400 MHz, DMSO-d6, 300 K) 8 1.20-1. 43 (m, 3H), 1.28 (T, J 7. 2 Hz, 3H) 1.63-1. 80 (m, 7H), 2.50-2. 58 (m, 1H, under DMSO), 2.80 (s, 3H), 2.90 (s, 3H), 3.51 (q, J 7. 2 Hz, 2H), 4.57 (s, 2H), 7.31-7. 36 (m, 2H), 7.49-7. 56 (m, 3H), 7.66 (d, J 9. 0 Hz, 1H), 7.85 (d, J 9. 0 Hz, 1H), 8.05 (s, 1H), 10.76 (br s, 1H) ; MS (ES+) m/z 496 (M+H) +.

The synthetic route of 1520-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2004/87714; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 749927-69-3, 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 749927-69-3 as follows.

A 200 liter reactor was charged with 4-bromo-2-fluoro-N-methylbenzamide (12.0 kg, 51.7 mole)1-Aminocyclobutane carboxylic acid(6.3 kg, 61.7 mole),Potassium carbonate (16.5 kg, 155 mole),2-acetylcyclohexanone (0.12 kg, 1.05 mole),1.2 liters of water, dissolved in 70 liters of DMF, under stirring with stirring CuI (0.2kg, 1.05mol)Heated to 110 degrees, the reaction 24 hours. After the reaction was completed, add water cooling 120 liters,Then add ethyl acetate extraction.The aqueous phase was retained, adjusted to pH = 1 with 1 N hydrochloric acid and the precipitated solid was filtered. Beating with water,Get pure 11.8 kg, product 86%.

According to the analysis of related databases, 749927-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Xipu Pharmaceutical Technology Co., Ltd.; Lianyungang Shengfeng Chemical Co., Ltd.; Qin Yong; Chen Yue; Bian Junjie; Yu Jianhua; Wang Mingfa; Dai Xiaoming; (6 pag.)CN107501237; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature 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