Tag: M.W=100-200

Electric Literature of 22246-76-0, These common heterocyclic compound, 22246-76-0, name is 8-Amino-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one, 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.

Example No. 217Preparation of methyl 3- (7- ( (2-oxo-2 , 3 , 4 , 5-tetrahydro-lH- benzo [b] azepin-8-yl) amino) -IH-pyrazolo [4, 3-d] pyrimidin- 5- yl) benzoate methyl 3- (7-chloro-2- (4-methoxybenzyl) -2H-pyrazolo [4,3- d] pyrimidin- 5 -yl) benzoate (0.16 mmol) and 8 -amino-4 , 5 -dihydro- lH-benzo [b] azepin-2 (3H) -one (0.3 mmol 2 eq. , ) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 428.1868 g/molHPLC-MS: analytical method Lrt: 4.65 min – found mass: 429 (m/z+H)

The synthetic route of 22246-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); A1;,
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2227-79-4, name is Benzothioamide, 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. Product Details of 2227-79-4

A mixture of benzenecarbothioamide (6.86 g) , 1,3- dichloroacetone (6.35 g) and toluene (50 mL) was heated under reflux for 3 hr. The reaction mixture was cooled, and water was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (9.77 g) . MS: [M+H]+ 210.1.

The synthetic route of 2227-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAJITA, Yuichi; MIKAMI, Satoshi; MIYANOHANA, Yuhei; KOIKE, Tatsuki; DAINI, Masaki; OYABU, Norio; OGINO, Masaki; TAKEUCHI, Kohei; ITO, Yoshiteru; TOKUNAGA, Norihito; SUGIMOTO, Takahiro; MIYAZAKI,Tohru; ODA, Tsuneo; HOASHI, Yasutaka; HATTORI,Yasushi; IMAMURA, Keisuke; (413 pag.)WO2019/27058; (2019); A1;,
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Electric Literature of 55512-05-5,Some common heterocyclic compound, 55512-05-5, name is 3-(Methylsulfonamido)benzaldehyde, molecular formula is C8H9NO3S, 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.

Under argon and at 0 C., 83 mg (0.417 mmol) of N-(3-formylphenyl)methanesulfonamide (Example 86A) were initially charged in 1 ml of abs. tetrahydrofuran. At 0 C., 99 mg (0.833 mmol) of methylmagesium bromide (3 M in diethyl ether) were added dropwise (resulting in the formulation of a precipitate), and the reaction solution was stirred at this temperature for 2 h. The reaction solution was quenched with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Yield: 80 mg (89% of theory) LC-MS (Method 8): Rt=1.15 min; MS (ESIpos): m/z=214 [M-H]-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Methylsulfonamido)benzaldehyde, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Vakalopoulos, Alexandros; Meibom, Daniel; Nell, Peter; Sussmeier, Frank; Albrecht-Kupper, Barbara; Zimmermann, Katja; Keldenich, Joerg; Schneider, Dirk; Krenz, Ursula; US2013/210795; (2013); A1;,
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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. 5763-44-0, name is Tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione, A new synthetic method of this compound is introduced below., Formula: C7H9NO2

tert-Butyl 4-(4-chloro-2-(2-((1,3-dioxohexahydrocyclopenta[c]pyrrol-2(1H)-yl)methyl)thieno[3,2-b]pyridin-7-yl)-6-methylphenoxy)piperidine-1-carboxylate. To diisopropyl azodicarboxylate (99 mg, 0.49 mmol) and tert-butyl 4-[4-chloro-2-[2-(hydroxymethyl)thieno[3,2-b]pyridin-7-yl]-6-methyl-phenoxy]piperidine-1-carboxylate (30 mg, 0.06 mmol) in THF (5 mL) was added triphenylphosphine polymer bound (0.55 mmol) and 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (61 mg, 0.44 mmol). Stirred at 60 C. for 2 h. The mixture was filtered and the filtrate washed twice with EtOAc. Combined all organic phases and washed with water and brine. Concentrated under vacuo and purified by column chromatography with hexanes:EtOAc (70% to 100%) to give 26 mg (69%) of the title compound as a light yellow oil. [M+H] 610.0

The synthetic route of 5763-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLX Bio, Inc.; Biannic, Berenger; Han, Xinping; Hu, Dennis X.; Ketcham, John Michael; Leger, Paul Robert; Maung, Jack; Okano, Akinori; Schwarz, Jacob Bradley; Shibuya, Grant; Wustrow, David Juergen; Young, Kyle; US2019/142834; (2019); A1;,
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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. 354-38-1, name is 2,2,2-Trifluoroacetamide, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2,2,2-Trifluoroacetamide

Intermediate 186 (0.43 g, 1.22 mmol) was dissolved in DCM (20 mL) and 2,2,2- trifluroacetamide (0.28 g, 2.49 mmol), magnesium oxide (0.21 g, 5.1 mmol), rhodium(II) acetate dimer (0.028 g, 0.064 mmol) and iodobenzene I,I-diacetate (0.53 g, 1.65 mmol) were added. After 18 h at r.t. the pink solution was filtered through a pad of celite and concentrated in vacuo. The residue was purified by column chromatography (Si02, 20- 60% EtOAc:DCM) to yield the title compound (0.39 g, 90%). HPLC-MS : MH+ mlz 431 , RT 2.00 minutes

According to the analysis of related databases, 354-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
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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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, A new synthetic method of this compound is introduced below., name: N-Boc-(2-Aminoethyl)-N-methylamine

Step 1 [0216] A solution of N-Boc-N-methylethylenediamine (1 g, 5.74 mmol) and sulfamide (1.1 g, 11.48 mmol) in dioxane (20 mL) was stirred at reflux under N2 atmosphere (monitored by TLC). The mixture was then filtered to remove the insoluble material and the filtrate was concentrated under reduced pressure and treated with ethyl acetate. The insoluble material was again removed by filtration and the filtrate concentrated under reduced pressure to give the desired product in 96% yield.

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; FOB SYNTHESIS; WO2005/123066; (2005); A1;,
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Synthetic Route of 67442-07-3, 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 67442-07-3 as follows.

[0541] A mixture of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.288 mmol), potassium carbonate (60 mg, 0.43 mmol) and 2-chloro-N-methoxy-N-methylacetamide (200 mg) in DMF (1.5 mL) was shaken at room temp. for 48 hrs. The mixture was diluted with water (5 mL), and the resulting solid was collected by filtration. The crude solid was recrystallized from aq. ethanol to afford title compound (90 mg). The title compound is also a compound of formula I. [0542] Physical characteristics are as follows: [0543] 1H NMR (400 MHz, DMSO-d6) delta) 10.45 (1H), 8.73 (1H), 7.37 (4H); 7.26 (1H), 5.91 (1H), 5.47 (2H), 4.74 (2H), 4.54 (2H), 3.86 (3H), 3.16 (3H); HPLC ret time=2.86 min; MS (ES+) m/z 450, 452.

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Larsen, Scott D.; May, Paul; Romines, Karen; Schnute, Mark E.; Tanis, Steven P.; US2004/138449; (2004); A1;,
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142-26-7, name is N-Acetylethanolamine, 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

Example 5 This example illustrates an alternative method for producing (-)-halofenate. A 500-mL round-bottom flask with a magnetic stirrer is charged with 35.5 g (65.4 mmol) of the (-)-CPTA/(S)-(-)-1-(2-naphthyl)-ethylamine diastereomeric salt (98% ee), 89.0 g of 1,2-dichloroethane, and 35.5 mL of water. To the slurry is added 6.7 g (68 mmol) of 37% hydrochloric acid, and the mixture was stirred at ambient temperature to give two clear phases. The lower organic phase is removed and washed with 7.0 g of water. The organic phase is evaporated, then dissolved in 55.6 g of 1,2-dichloroethane and placed in a 250-mL round-bottom flask in a heating mantel with a magnetic stirrer and fitted with a reflux/distillation head. To the solution is added 7.5 mL (100 mmol) of thionyl chloride, and the solution is heated to reflux for 2 hours. Heating is continued to collect distillate. The solution is cooled to ambient temperature, then chilled in an ice bath for the addition of 25.85 g (251 mmol) of distilled N-acetylethanolamine (KF analysis 1176 and 1288 ppm water). The solution is added slowly with stirring to 9.90 g (71.6 mmol) of potassium carbonate in 36 g of water chilled in an ice bath. The reaction mixture is rinsed with 5 mL of 1,2-dichloroethane. The lower organic phase is removed and washed with 37 mL of water. The solution is evaporated to give an residue. The residue is treated with 54 g of heptane, and the solvent is removed to give a residue. To the residue is added 76 g of heptane, and the solvent is removed to give a residue. The residue is dissolved in 28 mL of 2-propanol at 40 C., then diluted with an additional 28 mL of 2-propanol and 334 mL of heptane. Cooling to ambient temperature gives a slurry which thickens upon cooling in an ice bath. After stirring for 2 hours, the solid is isolated by vacuum filtration, rinsed with 29 g of heptane, and dried to give (-)-halofenate.

The synthetic route of 142-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Metabolex, Inc.; US2007/73082; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 683-57-8, name is 2-Bromoacetamide, molecular formula is C2H4BrNO, 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 2-Bromoacetamide

In a 100 mL round bottom flask was added 3-chlorophenol (2.57 g, 20.0 mmol), 2-bromoacetamide (2.76 g, 20.0 mmol), potassium carbonate (5.53 g, 40.0 mmol) and acetone (40 mL),The reaction system was heated to 70C and reacted overnight.After the reaction is completed, the mixture is cooled to room temperature, filtered, and the solvent is evaporated to dryness under reduced pressure. The crude product is purified by column chromatography (petroleum ether/ethyl acetate (V/V) = 1/1) to give a white solid (3.22 g, 87).%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 683-57-8, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
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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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H17NO3

A solution of potassium tert-butoxide (1? 5eq) was added to a solution of (1-hydroxymethylcyclopropyl) -tert-butoxycarbonylamino in tetrahydrofuran [THF] at room temperature. After stirring for 30 min, 4-fluoro-2-isopropyl Oxy-1-nitrobenzene (1.3 eq) and heated to 50 C overnight. After completion of the reaction, the reaction solution was cooled, poured into water and extracted three times with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and then poured onto the column. PE [petroleum ether]: EA [ethyl acetate] Volume ratio) = 5: 1 to obtain compound 4-3.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Geng Meiyu; Song Zilan; Ai Qing; Liu Zhiqing; Chen Yi; Peng Xia; Ding Jian; (29 pag.)CN107216319; (2017); A;,
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