Month: September 2021

Related Products of 919475-15-3, These common heterocyclic compound, 919475-15-3, name is 2-(4-(Benzyloxy)phenyl)-N,N-dimethylacetamide, 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.

In certain embodiments, the following procedure was employed. 150 g of 2-(4- benzyloxy)phenyl-N,N-dimethylacetamide, 945 g (1062 mL) of THF was charged to a 5 L jacketed reactor. 550 mL of isopropylmagnesium chloride (2.0 M in tetrahydrofuran) was added and the mixture was stirred for 1 h. 115 g of cyclohexanone was added to the reactor and mixed for 1 h. 360 g of RedAI (sodium bis(2-methoxyethoxy)aluminum hydride-65percent w/w in toluene) was added to the reactor and stirred for 16 h. When the reaction was complete the mixture was- 66 -LAI-2932341vl added to 2005 g of 22percent w/w aqueous citric acid. 420 g (600 mL) of heptane was charged to the reactor and stirred for 15 min. The stirring was stopped and the top layer was removed. 250 g of 50percent NaOH was added to adjust the pH to 9-10, followed by stirring. 1114 g (1500 mL) of MTBE was added to the reactor. The mixture was warmed to 45 +/- 5°C to dissolve the solids. The stirring was stopped and the bottom layer was removed. The organic layer was washed twice with 750 g of water at 450C. 750 mL of MTBE was removed by distillation and 750 mL of methanol was added. About 750 mL of MTBE/methanol was removed by distillation and 300 g of methanol and 300 g of water were added. The slurry was cooled to 0 0C and stirred for 30 min. The slurry was filtered and the solid washed with 375 g of (4:1 methanohwater). The solid was dried to yield 161 g of 1-(2-(dimethylamino)-1-(4-benzyloxyphenyl)ethyl) cyclohexanol.[00261] In certain embodiments, the following procedure was employed. To a 200 gallon reactor was charged 22.98 kg of 2-(4-benzyloxy)phenyl-N,N-acetamide and 145.1 kg of THF. With agitation, the temperature was adjusted to 5 0C to 10 0C. To the reactor was charged 82.9 kg of isopropylmagnesium chloride, 2.0M in THF, while maintaining the temperature between 5 0C to 35 0C. The lines were rinsed with 2.78 kg of THF. The contents were agitated for 61 minutes at 10 0C to 20 0C. To the reactor was added 9.31 kg of cyclohexanone while maintaining the temperature between 5 0C to 35 0C. The lines were rinsed with 2.77 kg of THF. The temperature was adjusted to 15 0C to 25 0C and the contents were agitated for 17 minutes at this temperature range after which the reaction was complete. To the reactor was charged 55.8 kg of sodium bis(2-methoxyethoxy)aluminum hydride (65 wtpercent in toluene) while maintaining the temperature at 15 0C to 35 0C. The contents were agitated for 10 h (<3percent starting material remained). The reaction mixture was added to 334.1 kg of 22percent citric acid solution cooled to 0 0C to 2 °C. THF (22.9 kg) and n-heptane (63.3 kg) were added to the reaction. The mixture was agitated for 15 minutes then the stirring was stopped and the phases were allowed to separate. The top layer was removed and the reactor was charged with 45.4 kg of 50percent sodium hydroxide. The reactor was charged 169.9 kg of MTBE and the temperature was adjusted to 40-50 0C. The contents were agitated for 14 minutes and the agitation was stopped to allow the phases to separate for 15 minutes. The aqueous layer was removed and 115 L of USP purified water was added. The temperature was adjusted to 40 0C to 50 0C. The contents were agitated for 15 minutes and the agitation was stopped to allow the phases to separate for 13 minutes. The aqueous bottom layer was removed. The reactor was charged with 115 L of USP purified water and the temperature was adjusted to 40 0C to 50 0C. The contents were agitated for 15 minutes and the agitation was stopped to allow the phases to separate. The aqueous bottom layer was removed. The solution was distilled under vacuum to a final volume of 188 L. To the reactor- 67 -LAI-2932341vl was charged 115.2 kg of methanol and the solution was distilled under vacuum to a final volume of 131 L. To the reactor was charged 46.0 kg of methanol and 57 L of USP purified water. The temperature was adjusted to 0 0C. The slurry was stirred for 41 minutes at -5 0C to 5 CC and the mixture was filtered. The cake was washed with 46.2 kg of methanol and 11.6 kg of USP purified water (cooled to -5 0C to 5 0C). The wet cake (30.66 kg) was dried at 40-50 0C to yield 24.47 kg of 1-(2-(dimethylamino)-1-(4-benzyloxyphenyl)ethyl)cyclohexanol.

The synthetic route of 919475-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEPRACOR INC.; WO2008/103461; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, 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. Recommanded Product: 50667-69-1

A solution of 2-chloro-6-methyl-3-((2,2,2-trifluoroacetamido)methyl)benzoic acid (1.70 g, 5.75 mmol) in cone. HC1 (10 mL) and dioxane (2 mL) was heated at reflux for 12 h. The reaction mixture was concentrated and the concentrate was dissolved in THF (1 mL). The solution was treated with NaOH (690 mg, 17.25 mmol) in H20 (2 mL) at 0C followed by iert-butyl dicarbonate (2.51 g, 11.50 mmol). The reaction mixture was stirred rt for 16 h. The reaction mixture was acidified with IN HC1 and the pH was adjusted to 2-3. The reaction mixture was extracted with 5% MeOH in CHCI3. The organic layer was separated, dried, filtered and concentrated. The concentrate was dissolved in CH3CN (20 mL) and the solution was treated with K2CO3 (1.60 g, 11.50 mmol) and CH3I (11.50 mmol) at rt. Then the reaction mixture was heated at 50 C for 1-2 h before it was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The concentrated was purified by column chromatography to provide 1.4 g of the title product and methyl 3-(((ierf-butoxycarbonyl)amino)methyl)-6-chloro-2- methylbenzoate as mixture of products.

The synthetic route of 50667-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; PAWAR, Mahesh Yashwant; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/38308; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, 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 4815-28-5, Recommanded Product: 4815-28-5

General procedure: 1 mmol of 5-(2-thienyl)-3-isooxazol carboxylic acid and TEA (3 mmol) were stirred in 2,5 ml of anhydrous DCM. The mixture was cooled down to 0 C and 1.3 mmol of DIC was added in several portions. The mixture was stirred for 15 min and 1.33 mmol Hobt was added at once. The stirring was continued for half an hour and 1 mmol of glycine tert-butyl ester hydrochloride was added to the mixture. The reaction was warmed to RT and stirred overnight. The mixture was diluted with 15 ml of DCM and the organic layer was washed with 0.1 M hydrochloric acid solution and distilled water. The organic layer was dried over anhydrous Na2SO4 end evaporated under reduced pressure. The crude product was purified by column chromatography (n-hexane: chloroform). Yield white needles 60 %. 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide (1mmol) and tert-butyl ({[5-(2-thienyl)-3-isooxazol]carbonyl}amino) acetic acid (1 mmol) were treated as described for compound STK2 [8] The crude product was collected by filtration and purified by crystallization from ethyl acetate with addition of methanol yielding 42 % of desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, and friends who are interested can also refer to it.

Reference:
Article; Tomala, Marcin D.; Magiera-Mularz, Katarzyna; Kubica, Katarzyna; Krzanik, Sylwia; Zieba, Bartosz; Musielak, Bogdan; Pustula, Marcin; Popowicz, Grzegorz M.; Sattler, Michael; Dubin, Grzegorz; Skalniak, Lukasz; Holak, Tad A.; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 261 – 267;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 676371-64-5, 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 676371-64-5 as follows.

[0204] A solution of 16-1 ((prepared according to Eur. J. Org. Chem. 2004, 493- 498), 0.400 g, 1.67 mniol) in THF (6.2 mL) was cooled to 0 C and treated with MgBrCH3(4.0M in Et20, 2.1 mL, 6.22 mmol). After 15 mins, the reaction was warmed to rt. After 4 h, the reaction was cooled to 0 C and quenched with sat. aq. NH4CI solution (5 mL). After warming to rt, the reaction was diluted with EtOAc and H2O. The organic layer was separated. The aqueous layer was saturated with NaCl(s) and then extracted with EtOAc (3 x 20 mL). The combined organics were dried (Na2S04) and concentrated under reduced pressure to afford an oil that was further purified by flash chromatography (S1O2, 0-100% EtOAc/Hexanes) to afford 16-2 (0.190 g, 63%) as a colorless oil. 1H NMR (400 MHz, CDCb) delta 1 .93 (s, 6H), 1 .47 (s, 9H), 1.21 is. 6H).

According to the analysis of related databases, 676371-64-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KALYRA PHARMACEUTICALS, INC.; BUNKER, Kevin, Duane; GUO, Chuangxing; GRIER, Mark, Charles; HOPKINS, Chad, Daniel; PINCHMAN, Joseph, Robert; SLEE, Deborah, Helen; HUANG, Qinhua; KAHRAMAN, Mehmet; (122 pag.)WO2016/44331; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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. Computed Properties of C9H20N2O2

A mixture of methyl 2-benzyl-4-chloro-9H-pyrimido[4,5-b]indole-7-carboxylate (0.100 g, 0.284 mmol), Et3N (0.079 mL, 0.569 mmol) and tert-butyl (3-aminopropyl)(methyl)carbamate (0.080 g, 0.426 mmol) in MeOH (1 mL) was heated in a microwave oven at 140C for 40 minutes. The solvent was removed under reduced pressure and the residue was purified by flash chromatography to give 0.092mg of crude Boc derivative which was used directly in the next step. TFA (1.0 ml, 12.98 mmol) was added dropwise to a cold suspension of methyl 2-benzyl -((3-((tert- butoxycarbonyl)(methyl)amino)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.092 g, 0.183 mmol) and the mixture was allowed to warm to room temperature over 30 minutes. After dilution with toluene, the solvent was removed under reduced pressure and then the residue was diluted with EtOAc to produce 85mg of a solid used directly in the next step: HRMS m/z 404.2091 (M+H)+.

The synthetic route of 150349-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; SAUVAGEAU, Guy; GAREAU, Yves; RUEL, Rejean; GINGRAS, Stephane; FARES, Iman; WO2013/110198; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 16982-21-1, 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. 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-(5-Bromo-lH-pyrrolo[2, 3-bJpyridin-3-yl)-thiazole-2-carboxylic acid ethyl ester (XXIII-a)(XXI-a) (XXIII-a)To a stirred solution of (XXI-a) (4.97 g, 15.6 mmol) in dioxane (55 mL) was added ethyl thiooxamate (2.29 g, 17.2 mmol). The reaction mixture was stirred vigorously at 950C for 18 h. The hot reaction mixture was filtered and the collected product was washed with cold dioxane (25 mL) to afford the hydrobromide salt of (XXIII-a) as a yellow powder (6.08 g, 14.0 mmol, 90%). 1H NMR (400 MHz, CDCl3) delta 1.48 (t, J = 7.1 Hz, 3H), 4.52 (q, J = 7.1 Hz, 2H), 7.77 (s, IH), 8.05 (s, IH), 8.43 (d, J= 1.8 Hz, 1 H), 9.21 (s, IH).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 2-amino-2-thioxoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EISAI LONDON RESEARCH LABORATORIES LIMITED; WO2008/95943; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1565-17-9, name is 4-Acetylbenzenesulfonamide, 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. Computed Properties of C8H9NO3S

General procedure: An isocyanate was prepared in situ from the corresponding amine by dissolving di-tert- butyl dicarbonate (1.1 eq.) in tetrahydrofuran (THF) (3 mL/mmol amine), treating with A V-dimethylpyridin-4-amine (DMAP) (1.1 eq.) and stirring for 5 min at room temperature before adding the amine (1 eq.) and stirring for a further 20 min. (0244) Meanwhile a sulfonamide sodium salt was prepared in situ by dissolving the a sulfonamide (1 eq.) in THF (3 mL/mmol), treating with NaH (1.0 eq., 60% oil dispersion) and stirring under reduced pressure until effervescence ceased (ca. 5-10 min). The sulfonamide salt and isocyanate solutions were combined and stirred at room temperature for 15 h under N2 atmosphere, monitored by LC-MS. Reaction mixtures were concentrated in vacuo, dissolved in the minimum volume 1:1 CH3CN / dimethylformamide (DMF) and purified via reverse phase MPLC. Typically a four minute aqueous wash was followed by a 15 min 10 mM NH4HC03(aq)/CH3CN gradient.

The synthetic route of 1565-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF QUEENSLAND; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH NEAR DUBLIN; O’NEILL, Luke; COLL, Rebecca; COOPER, Matthew; ROBERTSON, Avril; SCHRODER, Kate; MACLEOD, Angus Murray; MILLER, David John; (109 pag.)WO2018/215818; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, 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. Recommanded Product: 14719-21-2

B. PREPARATION OF 5-(3-TRIFLUOROACETAMIDO1-PROPYNYL)2′-DEOXYCYTIDINE (56) Iodide 55 (353.1 mg, 1.00 mmol) was coupled for 4 h to N-propargyltrifluoroacetamide following the general procedure given in EXAMPLE 1C. Chomatography of the crude product with a 0-20% methanol in dichloromethane gradient afforded 3.84 g, (102%) of white powder after vacuum drying overnight. This material was homogeneous by TLC, but tenaciously retained solvent. Recrystallization of this powder from boiling isopropanol (10 mL) and cooling to -20 afforded 299.6 mg (74%) alkynylamino nucleoside 56 as white needles (mp 168-170). NMR showed that the recrystallized product was homogeneous and that the crystals contained 0.5 molecules of isopropanol per molecule of product 56.

The synthetic route of 14719-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US5047519; (1991); A;,
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. 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 2-amino-2-thioxoacetate

To a solution of ethyl thiooxamate (10.0 g, 75 mmol) in dichloromethane (400 mL) was slowly added trimethyloxonium tetrafluoroborate (13.1 g, 89 mmol) at 0 C. After 10 min the ice bath was removed, and the reaction mixture was stirred overnight. The solvent was removed to afford ethyl 2-imino-2-(methylthio)acetate (12.Og, 66.6%) as tetrafluoroborate salt which was used without further purification.

The synthetic route of 16982-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; ANAND, Neel, Kumar; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUHR, Chris, Allen; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen; JOSHI, Anagha; KIM, Angie, Inyoung; TSUHAKI, Amy, Lew; MA, Sunghoon; MANALO, Jean-claire, Limun; NG, Stephanie; PETO, Csaba, J.; RICE Kenneth D.; TSANG, Tsze, H.; ZAHARIA, Cristiana, A.; WO2010/135524; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, 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 35303-76-5, COA of Formula: C8H12N2O2S

General procedure: To a cooled solution of triphosgene (1.41mmol) in THF at 0°C, a mixture of primary amine (3.52mmol) and N,N-diisopropylethylamine (DIPEA, 7.04mmol) was added. The reaction mixture was stirred at the same temperature for 30min and then the other amine (3.52mmol) was added. The reaction mixture was slowly allowed to attain ambient temperature and further stirred for 8h. After the completion of the reaction, water was added to the reaction mixture and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was subjected to column chromatography to obtain the pure compounds.

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:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Boggu, Pulla Reddy; Sharma, Niti; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Son, Min-Jeong; Woo, Sun-Hee; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1869 – 1887;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics