Tag: M.W=0-100

Electric Literature of 631-58-3, These common heterocyclic compound, 631-58-3, name is Propanethioamide, 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.

A mixture of propanethioamide (69 mg, 0.78 mmol) and (S)-tert-butyl 4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-ylcarbamate, 7, (0.300 g, 0.77 mmol) in CH3CN (4 mL) is refluxed for 2 hours. The reaction mixture is cooledto room temperature and diethyl ether is added to precipitate the intermediate 2-(nitrophenyl)-(S)-1-(4-ethylthiazol-2-yl)ethylamine which is isolated by filtration as the hydrobromide salt. The hydrobromide salt is dissolved in DMF (8 mL)together with diisoproylethylamine (0.38 mL, 2.13 mmol), 1-hydroxybenzotriazole (107 mg, 0.71 mmol) and (S)-(2-methoxycarbonyl-amino)-3-phenylpropionic acid (175 mg, 0.78 mmol). The mixture is stirred at 0 C for 30 minutes thenat room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combinedorganic phase is washed with 1 N aqueous HCl, 5 % aqueous NaHCO3, water and brine, and dried over Na2SO4. Thesolvent is removed in vacuo to afford 0.300g (81% yield) of the desired product which is used without further purification.LC/MS ESI+MS 483 (M+1).

Statistics shows that Propanethioamide is playing an increasingly important role. we look forward to future research findings about 631-58-3.

Reference:
Patent; Aerpio Therapeutics, Inc.; PETERS, Kevin, G.; SHALWITZ, Robert; (176 pag.)EP2624916; (2018); B1;,
Amide – Wikipedia,
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Application of 3144-09-0, These common heterocyclic compound, 3144-09-0, name is Methylsulfonamide, 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.

CH2Cl2 (3.06 ml) was added to the 20 mL Scint vial containing DMAP (5.61 mg, 0.046 mmol), 2-chloro-1-methylpyridin-1-ium iodide (0.282 g, 1.102 mmol), benzoic acid 1a (0.1122 g, 0.919 mmol), methanesulfonamide 2a (0.175 g, 1.837 mmol) at room temperature. After stirring for 5 min, TEA (0.38 ml, 2.76 mmol) was slowly added to the reaction mixture. The reaction was stirred at room temperature for 1 hour. The reaction solvent was removed via vacuum and the crude was taken up in ethyl acetate, washed with 1N HCl. The ethyl acetate layer was separated, dried (Na2SO4), filtered and concentrated. The crude was purified by flash column eluted with ethyl acetate in hexane from 0 to 50% to 100% to give the desired product 3a as a white solid. (0.1409 g, 77%). 1H NMR (400 MHz, CHLOROFORM-d) delta 8.96 (br s, 1H), 7.95 – 7.82 (m, 2H), 7.68 – 7.61 (m, 1H), 7.56 – 7.49 (m, 2H), 3.46 (s, 3H); 13C NMR (126 MHz, CHLOROFORM-d) delta 165.5, 133.9, 131.0, 129.1, 127.9, 41.8; HRMS(ESI-) : observed: 198.0221; theory: 198.0217.

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Ling; Luo, Guanglin; Tetrahedron Letters; vol. 60; 3; (2019); p. 268 – 271;,
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 6228-73-5 as follows. Quality Control of Cyclopropanecarboxamide

Cyclopropanecarboxamide (22.5 mg, 0.26 mmol) was combined with Int3 (30 mg, 0.088 mmol). Dimethylacetamide (DMA, 0.6 mL) was added to the vessel, followed by the addition of tris (diphenylmethyleneacetone) dicum (0) (Pd2dba3, 8.1 mg, 0.0088 mmol)4,5-bis (diphenylphosphino) -9,9-dimethyl(Xantphos, 10 mg, 0.018 mmol) and cesium carbonate (115 mg, 0.35 mmol). The vessel was then evacuated and backfilled three times with nitrogen and heated to 145 & lt; 0 & gt; C for 1 hour.The reaction was cooled to room temperature and then diluted with ethyl acetate (EtOAc, ca. 250 mL). The solution was washed twice with water, dried over sodium sulfate (Na2SO4), filtered, concentrated and purified using preparative HPLC. The product in the form of TFA salt was collected and then dissolved in about 15 mL of water, to which about 100 mL of saturated sodium bicarbonate (NaHCO3, an aqueous solution) was added and stirred for 10 minutes. The product of (x3) was extracted from the slurry using dichloromethane (DCM), dried over sodium sulfate, filtered, concentrated and collected to give 16.3 mg of 1 (48% yield).

According to the analysis of related databases, 6228-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN,, RYAN M.; WEINSTEIN,, DAVID S.; WROBLESKI,, STEPHEN T.; ZHANG,, YANLEI; TOKARSKI,, JOHN S.; MERTZMAN,, MICHAEL E.; LIU,, CHUNJIAN; (124 pag.)TWI582077; (2017); B;,
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Synthetic Route of 598-55-0, 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. 598-55-0, name is Methyl carbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a well-ground mixture of beta-naphthol (0.288 g, 2 mmol), aldehyde (2 mmol) and amide derivatives (2.4 mmol) in a 10 mL round-bottomed flask connected to a reflux condenser, was added TrCl (0.055 g, 0.2 mmol), and the resulting mixture was stirred in an oil-bath (70 C) for the times reported in Table 2. Afterward, petroleum ether (20 mL) was added to the reaction mixture, refluxed, and stirred for 3 min, and filtered (TrCl is soluble in petroleum ether; however, the products are insoluble in this solvent). The filtrate containing the catalyst was washed two times with 20 mL of 40% (w/v) solution of NaHSO3 in H2O/EtOH (4:1) to extract the unreacted aldehyde dissolved in the petroleum ether. The organic layer was separated and dried with CaCl2; the solvent was evaporated to give pure recycled TrCl. The solid residue was recrystallized from EtOH (95%) to give the pure product (compounds 1a-m, 2a-d, and 3a-e).

The chemical industry reduces the impact on the environment during synthesis Methyl carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Khazaei, Ardeshir; Zolfigol, Mohammad Ali; Moosavi-Zare, Ahmad Reza; Abi, Fereshteh; Zare, Abdolkarim; Kaveh, Hamideh; Khakyzadeh, Vahid; Kazem-Rostami, Masoud; Parhami, Abolfath; Torabi-Monfared, Hossein; Tetrahedron; vol. 69; 1; (2013); p. 212 – 218;,
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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. 15910-91-5, name is 1-Methylcyclopropanecarboxamide, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

A -78 C. solution of 1-methylcyclopropanecarboxamide (1.35 g, 13.6 mmol) in THF (30 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1M THF, 17.7 mL, 17.7 mmol), stirred for 0.5 h, treated drop-wise with a solution of isopropenyl chloroformate (1.94 mL, 17.7 mmol) in THF (5 mL), stirred at -78 C. for 1 h, then allowed to warm to RT and stirred for 1 h. The mixture was quenched with satd. NaHCO3, extracted with EtOAc (3*) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford crude prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate (2.9 g, 116%) which was used without further purification.

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; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Kaufman, Michael D.; Patt, William C.; Ahn, YuMi; US2014/275016; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 6228-73-5, 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. 6228-73-5, name is Cyclopropanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows.

Example A7 A suspension of Example A1 (2.00 g, 7.95 mmol), Cs2CO3 (5.00 g, 15.35 mmol), XPhos (0.200 g, 0.420 mmol), Pd2(dba)3 (0.200 g, 0.218 mmol) and cyclopropylcarboxamide (1.00 g, 11.75 mmol) in dioxane (20 mL) was heated at 90 C. under argon overnight. The mixture was cooled to RT and the solids removed via filtration and washed with DCM and THF. The filtrate was concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (1.52 g, 64%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.01 (s, 1H), 8.57 (dd, J=2.8, 0.5 Hz, 1H), 8.40 (m, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.98 (dd, J=8.9, 2.8 Hz, 1H), 7.85 (d, J=2.4 Hz, 1H), 6.89 (dd, J=5.7, 2.4 Hz, 1H), 1.97 (m, 1H), 0.77 (m, 4H); MS (ESI) m/z: 301.1 (M+H+).

The chemical industry reduces the impact on the environment during synthesis Cyclopropanecarboxamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Kaufman, Michael D.; Patt, William C.; Ahn, YuMi; US2014/275016; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 563-83-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 563-83-7 name is Isobutyramide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A 15 mL round-bottom flask was charged with a stirring bar, 2.0 mL ethyl acetate, N,N-dimethylaniline derivative (0.9 mmol), amide (0.5 mmol) and complex 2 (27.9 mg, 0.05 mmol) were added. After stirring 15 min, TBHP (0.75 mmol, 108 mL) was added without extrusion of the air. The mixture was stirred for 8 h at 40 oC. After cooling to room temperature, 10 mL ethyl acetate was added, and the mixture was filtered. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel using ethyl acetate/pet ether (60-90 oC) as eluent to give the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Isobutyramide, and friends who are interested can also refer to it.

Reference:
Article; Zhu, Fan; Lu, Bing; Sun, Hongmei; Shen, Qi; Tetrahedron Letters; vol. 57; 37; (2016); p. 4152 – 4156;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 631-58-3,Some common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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.

Ethyl chloroacetate (1 equiv) was dissolved in dry acetone, and a solution of thiopropanamide (1 equiv) in acetone was added. The reaction was refluxed overnight. After cooling to rt, volatiles were evaporated. The residue was diluted with ethyl acetate followed by careful addition of saturated NaHCO3 (aq). Layers were separated and the aqueous layer was extracted with ethyl acetate (2x), organics were combined, dried (Na2SO^ and concentrated to give a yellow residue. Purification by column chromatography on silica gel (ethyl acetate: hexanes: 80:20) provided (2-Ethyl-thiazol~4-yl)-acetic acid ethyl ester in 45 % yield, m/z (ES+) 200 (M+H4″).

The synthetic route of 631-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; NEUROGEN CORPORATION; WO2006/122200; (2006); 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 598-55-0 as follows. Product Details of 598-55-0

To a mixture of beta-naphthol (0.144 g, 1 mmol), arylaldehyde (1 mmol) and alkylcarbamate (1.3 mmol) in a test tube, was added nano-SB-[PSIM]Cl (0.01 g), and the resulting mixture was stirred magnetically at 70 C, and after solidification of the reaction mixture with a small rod at that temperature. The mixture was cooled to room temperature, then warm EtOAc (5 mL) was added and stirred for 1 min followed by centrifugation and decanting to separate nano-SB-[PSIM]Cl (the silica-bonded IL is not soluble in warm EtOAc, but the unreacted starting materials and the product are soluble in it). The separated EtOAc was evaporated, and the solid residue was recrystallized from hot EtOH (95 %) to give the pure alpha-carbamatoalkyl-beta-naphthol.

According to the analysis of related databases, 598-55-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zare, Abdolkarim; Merajoddin, Maria; Moosavi-Zare, Ahmad Reza; Zarei, Mahmoud; Beyzavi, M. Hassan; Zolfigol, Mohammad Ali; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2365 – 2378;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 563-83-7, These common heterocyclic compound, 563-83-7, name is Isobutyramide, 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 solution of 38 phosphorus pentasulfide (P2S5) (4.58mmol) in ether (8ml) was added 39 isobutylamide 11a (1gm, 11mmol) and the reaction mixture was stirred for 2h at room temperature. The reaction mixture was diluted with brine and extracted with ether. The organic layer was dried over Na2SO4 and evaporated to give crude 40 thioamide. The mixture of crude 40 thioamide and 42 ethyl alpha-bromopyruvate (11.42mmol) in 43 EtOH (10ml) was stirred at reflux temperature for 30min. The solvent was evaporated under vacuum, diluted with EtOAc and washed with 7% aqueous NaHCO3 (3¡Á30mL), the organic layer was dried over Na2SO4 and evaporated to get crude product, which was purified by column chromatography (n-hexane/EtOAc) to afford 44 12a.

Statistics shows that Isobutyramide is playing an increasingly important role. we look forward to future research findings about 563-83-7.

Reference:
Article; Karale, Uttam B.; Krishna, Vagolu Siva; Krishna, E. Vamshi; Choudhari, Amit S.; Shukla, Manjulika; Gaikwad, Vikas R.; Mahizhaveni; Chopra, Sidharth; Misra, Sunil; Sarkar, Dhiman; Sriram, Dharmarajan; Dusthackeer, V.N. Azger; Rode, Haridas B.; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 315 – 328;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics