Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 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 127828-22-2, HPLC of Formula: C9H20N2O3

To a stirred solution of 5g of 2-{(3-butynyl)-l-oxy}ethyl methanesulfonate and 5.32g of 2-[2-{2-(t-butoxycarbonyl)amino}ethyl-l- oxy]ethylamine in 60ml acetonitrile, was added drop-wise 3.6g of potassium carbonate dissolved in water at O0C. The reaction solution was allowed to slowly warm to RT and stirred for another 24h, and then concentrated under reduced pressure. The resulting residue was dissolved in MC and washed with water. The organic layer was concentrated and dissolved in 80ml THF and 80ml water, to which was added 8.4g of BoC2O dissolved in 50ml THF. The reaction mixture was stirred at RT for 16h, which was followed by removal of THF in vacuo and extraction with EA. The organic layer was washed in series with 0.5M aq citric acid, water, and brine. The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (hexane -> 1:4 EA/hexane) to obtain 2.45g of compd 9 as a pale yellow oil. 1H NMR (400MHz; CDCI3) delta 5.08 (br s, 0.5H), 4.93 (br s, 0.5H), 3.61-3.46 (m, 12H), 3.31 (m, 2H), 2.48 (m, 2H), 1.99 (t, IH), 1.48 (s, 9H), 1.46 (s, 9H).

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; CTI BIO; WO2009/113828; (2009); A2;,
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. 28797-48-0, name is 11-(2-Chloroacetyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 11-(2-Chloroacetyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one

EXAMPLE 7 5,11-Dihydro-11-[[[2-(1-ethyl-2-pyrrolidinyl)ethyl]amino]acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one Prepared analogously to Example 1 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 2-(2-aminoethyl)-1-ethylpyrrolidine. Yield: 9.5% of theory, Mp.: 109-111 C. (ethyl acetate/cyclohexane 2/1 v/v).

According to the analysis of related databases, 28797-48-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mihm; Gerhard; Eberlein; Wolfgang; Engel; Wolfhard; Trummlitz; Gunter; Mayer; Norbert; de Jonge; Adrian; Doods; Henri; US5002943; (1991); A;,
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: 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

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

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

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

Electric Literature 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

22117-85-7, name is 2-Methoxy-5-sulfamoylbenzoic 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. Application In Synthesis of 2-Methoxy-5-sulfamoylbenzoic acid

EXAMPLE 53 N-(1-Cyclohexyl-3-pyrrolidinyl)-2-methoxy-5-sulfamoylbenzamide To 3.7 g. (0.022 mole) of 3-amino-1-cyclohexylpyrrolidine in 100 ml. of pyridine was added dropwise with cooling 1.1 g. (0.008 mole) of phosphorous trichloride at 20C. After stirring one hour, 3 g. (0.013 mole) of 2-methoxy-5-sulfamoylbenzoic acid was added and refluxed 6 hrs. The solution was concentrated and the residue partitioned between dilute hydrochloride acid and isopropyl ether. The acid was made basic with ammonium hydroxide and extracted with chloroform which was dried (sodium sulfate) and concentrated. The residue was crystallized from ethyl acetate and recrystallized from isopropyl alcohol. Yield 1 g. (33%); m.p. 184-187C. Anaylsis: Calculated for C18 H27 N3 O4 S: C,56.67; H,7.13; N,11.02. Found: C,56.39; H,7.09; N,11.00.

The synthetic route of 22117-85-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; A. H. Robins Company, Incorporated; US3966957; (1976); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1151665-15-4, 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. 1151665-15-4, name is tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 3-(2-chloro-7, 8-dihydro- 1, 6-naphthyridin- 6(5H)-yl)-2-methylpropanoate was prepared starting from tert-butyl 2-chloro- 7,8- dihydro- 1,6- naphthyridine- 6(5H) – carboxylate in accordance with scheme 6. Tert-butyl 2-chloro-7,8-dihydro-1,6- naphthyridine-6(5H)-carboxylate (3.22 g; 12 mmol; 1 eq) was dissolved in DCM (100 mL). TFA (13.7 g; 120 mmol; 10 eq) was added under stirring at RT. Themixture was stirred for 20h at RT. 50 mL of a saturated NaHCO3 solution was added followed by the addition of solid NaHCO3 while stirring until the pH of the aqueous phase was 7. After phase separation, the organic phase was dried with MgSO4 and evaporated. The aqueous phase was saturated with NaC1 under stirring foliowed by addition of 200 mL DCM and stirring for 30 mm. After phaseseparation, the organic phase was dried with MgSO4 and evaporated. The yield of the combined product 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine was 2.01 g (11.92 mmol; 99%).

The synthetic route of tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; LANGE, Udo; OCHSE, Michael; VAN DER KAM, Elizabeth; VAN BERGEIJK, Jeroen; TURNER, Sean; OELLIEN, Frank; WALLESER, Patrick; AMBERG, Wilhelm; HORNBERGER, Wilfried; GENESTE, Herve; MEZLER, Mario; HUTCHINS, Charles; (301 pag.)WO2017/36978; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics