Tag: M.W=200-300

Electric Literature of 201162-53-0,Some common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, molecular formula is C11H20N2O2, 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.

To a solution of /er/-butyl 3,8-diazabicyclo[3.2. l]octane-3-carboxylate (1.0 equiv) and DIEA (2.0 equiv) in dry DCM at 0C was added BrCN (1.5 equiv). The mixture was stirred at 0C for lh and then at rt overnight. The reaction mixture was washed with water and brine to afford /c/7-butyl 8-cyano-3,8-diazabicyclo[3.2.l]octane-3-carboxylate which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Boc-3,8-Diazabicyclo[3.2.1]octane, its application will become more common.

Reference:
Patent; ESCALIER BIOSCIENCES B.V.; MOHAN, Raju; NUSS, John; HARRIS, Jason; YUAN, Shendong; (144 pag.)WO2019/177996; (2019); A1;,
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Application of 53844-02-3, A common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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.

To a stirred solution of bromide (1 mmol) and 4-amino-1-butanol (0.36 g, 4 mmol, 4 eq.) in anhydrous DMF (10 ml) under N2, was added anhydrous K2CO3 (0.276 g, 2 mmol, 2 eq.) and sodium iodide (15 mg, 0.1 mmol, 0.1 eq.). The reaction was stirred for 72 hours at room temperature, until reaction complete. The DMF was evaporated in vacuo and dried exhaustively under high vacuum. The resulting oily solid was redissolved in CH2Cl2 (100 ml) and washed with water (4 x 50 ml). The combined aqueous extracts were then washed with CH2Cl2 (40 ml) and the CH2Cl2 extracts dried over anhydrous Na2SO4. The CH2Cl2 was evaporated in vacuo to give a pale yellow oil.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; IC-VEC LIMITED; EP918790; (2004); B1;,
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These common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, 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. Quality Control of tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

To a solution of (1R,3r,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (9.0 g) in DCM (200 mL) was added TEA (11.0 mL) and MsCI (3.7 mL). Theresulting mixture was stirred at 0C for 2 hours, and then diluted with water (100 mL). The reaction mixture was extracted with DCM (2×200 mL). The combined organic layers were washed, dried and concentrated to afford (1 R,3r,5S)-tert-butyl 3-((methylsulfonyl)oxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (12.0 g).

The synthetic route of tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEN, Weichun; IGBOKO, Ebere F; LIN, Xichen; LU, Hongfu; REN, Feng; WREN, Paul Bryan; XU, Zhongmiao; YANG, Ting; ZHU, Lingdong; WO2015/181186; (2015); A1;,
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Related Products of 207405-68-3, 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. 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound ii-35a (5.00 g, 22.19 mmol) in methanol (100 mL) and water (10 mL) were added ammonium formate (13.99 g, 222 mmol) and 10%-palladium/carbon (2.362 g) in turn. The resultant was stirred at room temperature for 2 days. Celite was used to filtrate the reaction liquid, and then the filtrate was diluted with chloroform, washed with an aqueous sodium hydroxide solution and a saturated salt solution, and dried over magnesium sulfate. Magnesium sulfate was filtrated off, and then the liquid was concentrated under reduced pressure to yield compound ii-35b (5.60 g). Compound ii-35b yielded was used as it was, without being purified, in the next reaction.The total amount of compound ii-35b yielded was dissolved in methanol (50 mL) and acetic acid (5 mL). Thereto were then added a 36% aqueous formalin solution (8.49 mL, 111 mmol) and hydrogenated sodium triacetoxyborate (9.41 g, 44.4 mmol) in turn. The resultant was stirred at room temperature for 1 hour. To the reaction liquid was added an 8 N aqueous sodium hydroxide solution to set the pH thereof to 10. Thereafter, this liquid system was subjected to extraction with chloroform. To the organic phase was added a 0.5 N aqueous hydrochloric acid solution, and then the liquid-system was separated to two phases. Thereafter, the water phase was made into basicity, and then subjected to extraction with chloroform. The organic phase was washed with a saturated salt solution, and dried over magnesium sulfate. Magnesium sulfate was filtrated off, and then the organic phase was concentrated under reduced pressure to yield compound ii-35c (2.43 g, 43%).1H-NMR (CDCl3) delta: 4.16 (2H, d, J = 29.04 Hz), 2.22 (6H, s), 2.12-1.59 (9H, m), 1.46 (9H, s).

The synthetic route of tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; HISAKAWA, Shinya; HASEGAWA, Yasushi; AOKI, Toshiaki; KUSANO, Hiroki; SANO, Masayuki; SATO, Jun; YAMAWAKI, Kenji; EP2557082; (2013); A1;,
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Electric Literature of 85006-25-3,Some common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, 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.

Tert-butyl (tert-butoxycarbonyl)oxycarbamate (70 mg) and 1- (bromomethyl) -2-fluorobenzene (56.7 mg) were dissolved in CH 2Cl 2(7 ml) . The mixture was added 1M NaOH (0.33 ml) and tetrabutylammonium bromide(4.83 mg) , and stirred at room temperature for overnight. The resulting mixture was washed with water and dried with Na 2SO 4, concentrated in vacuo and purification by silica gel chromatography to give tert-butyl ( (tert-butoxycarbonyl) oxy) (2-fluorobenzyl) carbamate (82 mg, 80%) . 1HNMR (400 MHz, CDCl 3): delta 7.31-7.37 (m, 4H) , 4.52(s, 2H) , 1.46 (s, 9H) , 1.44 (s, 9H) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (tert-butoxycarbonyl)oxycarbamate, its application will become more common.

Reference:
Patent; SU, Yaning; SIRONAX LTD; ZHANG, Zhiyuan; YANG, Yi; WANG, Guozheng; LIU, Wendong; MA, Yongfen; REN, Yan; (74 pag.)WO2020/103859; (2020); A1;,
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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 35303-76-5 as follows. HPLC of Formula: C8H12N2O2S

To solid reagents 4-(2-aminoethyl)benzenesulfonamide (2.00 g, 9.99 mmol) and dihydrofuran-2,5-dione (0.999 g, 9.99 mmol) was added THF (30 mL). The reaction mixture was stirred at 60 C for 7 hrs. Solvent was evaporated under reduced pressure to give 4-oxo-4-((4- sulfamoylphenethyl)amino)butanoic acid (3.00 g, 9.99 mmol, 100 % yield) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 12.09 (s, 1H), 7.96 (t, J = 5.6 Hz, 1H), 7.72 (d, J = 8.1 Hz, 2H), 7.38 (d, J = 8.1 Hz, 2H), 7.29 (s, 2H), 3.26 (q, J = 6.8 Hz, 2H), 2.76 (t, J = 7.2 Hz, 2H), 2.40 (t, J = 6.9 Hz, 2H), 2.27 (t, J = 6.9 Hz, 2H); MS (ESI), 301.1 (M+H)+.

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WAVE LIFE SCIENCES LTD.; ZHANG, Jason Jingxin; SHIVALILA, Chikdu Shakti; VARGEESE, Chandra; IWAMOTO, Naoki; (469 pag.)WO2019/75357; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6325-93-5, name is 4-Nitrobenzenesulfonamide, 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 6325-93-5, COA of Formula: C6H6N2O4S

Step 1 – Tert-butyl N-(4-nitrophenyl)sulfonylcarbamate (0596) [00375] To a solution of 4-nitrobenzenesulfonamide (5.00 g, 24.7 mmol) in anhydrous dichloromethane (40 mL) was added triethylamine (5.00 g, 49.4 mmol) and catalytic amount of N,N-dimethylpyridin-4-amine. The mixture was cooled to 0 C and di-tert-butyl dicarbonate (5.67 g, 25.9 mmol) was added over 10 min. Then the mixture was warmed to 18 C and stirred for 50 min. On completion, the reaction mixture was quenched with ice water (40 mL). Afterwards, the organic phase was separated, washed with brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 3:1 to 1:1) to give the title compound.1H NMR (400MHz, CDCl3) delta = 8.44 – 8.40 (m, 2H), 8.28 – 8.24 (m, 2H), 1.43 (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; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; SAIAH, Eddine; (264 pag.)WO2017/156181; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1259224-00-4, name is tert-Butyl (1-(4-aminophenyl)cyclobutyl)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 1259224-00-4, Recommanded Product: tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate

To the solution of 2,4-Dichloro-6-methyl-5-nitro-pyrimidine (2.08 g, lO.OOmmol) in THF (50 mL) at -78 C was slowly added the solution of [l-(4-Amino-phenyl)- cyclobutyl]-carbamic acid tert-butyl ester (2.62 g, 10.00 mmol) in THF (20 mL). The reaction mixture was stirred at ambient temperature for 30 min.. Then it was concentrated to remove the solvent. The obtained residue was dissolved in ethyl acetate (250 mL) and washed by saturated. NaHC03 solution, followed by brine. The separated organic layer was dried over sodium sulfate, filtered and concentrated to give { l-[4-(2-Chloro-6-methyl-5-nitro-pyrimidin-4-ylamino)-phenyl]- cyclobutyl}-carbamic acid tert-butyl ester. (4.3 g, 98%yield). MS (ESI+) e/z: 370.9 / 372.9 [M+l]+.

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.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
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Reference of 35303-76-5, A common heterocyclic compound, 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, molecular formula is C8H12N2O2S, 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.

General procedure: One equivalent (eq) of starting dichlorotriazinyl benzenesulfonamide(1, 2 or 3) [3] was dissolved in DMF as a solvent. Then 1 eq of solid anhydrous potassium carbonate was added in portions. After 10 min of stirring 1 eq of the appropriate nucleophile was addedalso in portions. Reaction was stirred at 35°C until disappearance of starting material (monitored by TLC: CH3OH was used as eluent,detection with UV light and ninhydrin). After completion of the reaction was crushed ice added to the reaction mixture and the precipitate formed was collected by filtration. Purification of a crude product was made by its solution in acetone and pure product was precipitated by addition of isopropyl alcohol.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Havrankova, Eva; Csoellei, Jozef; Vullo, Daniela; Garaj, Vladimir; Pazdera, Pavel; Supuran, Claudiu T.; Bioorganic Chemistry; vol. 77; (2018); p. 25 – 37;,
Amide – Wikipedia,
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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. 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H15Cl2NO2S

3.4 g (0.0156 mole) of levorotatory (-)-(4-chlorophenyl)phenylmethylamine(prepared in accordance with Example 1.1 of U.S. Patent No. 5478941 ) and 5.1 g(0.0172 mol) of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (prepared inExample 2.3 of U.S. Patent No. 5478941 ) in 6 ml_ (4.4 g or 0.0343 mol) of ethyldiisopropylamine are mixed in a 25 ml_ round-bottomed flask. The mixture is heated under reflux (127 0C) for 4 hours and then cooled, with stirring, to 86 0C and 13.8 ml_ of methanol are added at once. The mixture is then cooled in an ice bath and still stirred for 1 hour. The precipitate which forms is filtered off, washed with 10 ml_ of methanol and dried under vacuum at 40 0C. The product is recrystallized from a 3:1 (v/v) mixture of methanol and acetone. 6 g of levorotatory(-)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine are obtained.M. P: 171.1 0C. Yield: 87.2%.[alpha]D25: -40.68 (c=1 , toluene)Optical purity: 100%Analysis for C24H25CIN2O2S in %:CaIc: C 65.37, H 5.71 , N 6.35, Cl 8.04, S 7.27Found: C 65.95, H 5.80, N 6.60, Cl 8.12, S 7.33

According to the analysis of related databases, 42137-88-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; RAMAYYA, Vaddadi Pattabhi; WO2009/62036; (2009); A2;,
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Amide – an overview | ScienceDirect Topics