Month: September 2021

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

94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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. COA of Formula: C13H20N2O2

Tert-butyl (4-aminophenethyl)carbamate (2.33 g, 9.89 mmol, 1.0 eq) was dissolved in DCM (100 mL) and mixed with HBTU (3.75 g, 9.89 mmol, 1.0 eq) and cooled to 0C using an ice bath. Azidoacetic acid (1.0 g, 9.89 mmol, 1.0 eq) was added to the stirring mixture followed by NMM (2.18 mL, 19.79 mmol, 2.0 eq). The mixture was stirred 1 hour at 0C and 23 hours at room temperature. The mixture was then diluted with 0.5 M NaHC03 (100 mL) and the organic phase was separated. The aqueous phase was then extracted two times with 50 mL DCM, the combined organic phases dried over MgS04, filtered and concentrated in vacuo. The crude material was further purified using column chromatography on Si02 with 50-100% EtOAc in heptane as eluent. This gave a pale yellow solid.

The synthetic route of 94838-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITETET I OSLO; GOLDING, Louise; RONGVED, Pal; ASTRAND, Ove Alexander H°gmoen; SAMUELSEN, Ørjan; SCHNAARS, Christian; KILDAHL-ANDERSEN, Geir; (234 pag.)WO2018/33719; (2018); A1;,
Amide – Wikipedia,
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Electric Literature of 67074-78-6,Some common heterocyclic compound, 67074-78-6, name is 3,4-Dihydropyrido[2,3-b]pyrazin-2(1H)-one, molecular formula is C7H7N3O, 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.

F) N-(1-(4-methoxyphenyl)propyl)-2-oxo-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxamide To a solution of 3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one (23.5 mg) in a mixed solvent of tetrahydrofuran (5 mL) and N,N-dimethylacetamide (1 mL) were added triethylamine (65.9 muL) and bis(trichloromethyl)carbonate (46.8 mg) at 0C. The reaction mixture was stirred at 0C for 2 hr, triethylamine (65.9 muL) and 1-(4-methoxyphenyl)propan-1-amine hydrochloride (159 mg) were added thereto at 0C. The reaction mixture was stirred at room temperature for 2 hr, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and crystallized from hexane/isopropyl ether to give the title compound (6.3 mg). MS (API-): [M-H]- 339.0. 1H NMR (300 MHz, CDCl3) delta 0.79-1.00 (3H, m), 1.76-1.97 (2H, m), 3.78 (3H, s), 4.68 (2H, s), 4.83 (1H, q, J = 7.2 Hz), 6.86 (2H, d, J = 8.7 Hz), 6.96 (1H, dd, J = 7.7, 5.1 Hz), 7.08-7.37 (3H, m), 7.97 (1H, dd, J = 5.1,1.3 Hz), 9.69 (1H, brs), 10.35 (1H, d, J = 7.6 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Dihydropyrido[2,3-b]pyrazin-2(1H)-one, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIKAMI, Satoshi; NAKAMURA, Shinji; ASHIZAWA, Tomoko; SASAKI, Shigekazu; TANIGUCHI, Takahiko; NOMURA, Izumi; KAWASAKI, Masanori; EP2848618; (2015); 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 1015-89-0 as follows. 1015-89-0

(ii) BDS, THF, reflux, 24 h; (yield 20percent)

According to the analysis of related databases, 1015-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROBERTS, Edward; MITTAPALLI, Gopi Kumar; VELLUCCI, Danielle; YANG, Jun; GUERRERO, Miguel; URBANO, Mariangela; ROSEN, Hugh; WO2014/116684; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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 1314538-55-0, Product Details of 1314538-55-0

To a N2 purged flask containing O-Silyl imidazole 8a or 8b (2.0 mmol, 1.0 equiv.), Pd(OAc)2 (0.2 mmol, 0.1 eq.), XPhos (0.2 mmol, 0.1 eq.), tert- butoxycarbonyl)amino)methyl) trifluoroborate (2.2 mmol, 1.1 eq.) and K2C03 (6 mmol, 3.0 equiv.) was added 6 mL degassed toluene and 1.5 mL degassed water. The reaction was then heated to 75 C for 18 hours. Upon completion, the reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was then collected and dried over Na2S04 followed by filtration and concentration via rotary-evaporation. The crude material was then purified using silica gel column chromatography (2:1 Ethyl Acetate: Hexanes to 10:1 Ethyl Acetate: Hexanes) to yield the Boc- protected amino-product as a white solid (50-60% yield)

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, Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; HERGENROTHER, Paul J.; GEDDES, Emily Jane; DROWN, Bryon Shane; MOTIKA, Stephen E.; PARKER, Erika Nicole; (141 pag.)WO2019/177975; (2019); A1;,
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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 1346674-23-4,Some common heterocyclic compound, 1346674-23-4, name is 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one, molecular formula is C12H16N2O, 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 128a 2-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluorobenzaldehyde 128a A 100-mL round-bottomed flask equipped with a reflux condenser was charged with 4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one 103e (1.0 g, 4.90 mmol, 1.0 eq.), 2-bromo-6-chloro-4-fluorobenzaldehyde (2.76 g, 9.8 mmol, 2.0 eq.), Pd2(dba)3 (224 mg, 0.24 mmol, 0.050 eq.), Xantphos (283 mg, 0.49 mmol, 0.10 eq.), potassium acetate (1.44 g, 14.7 mmol, 3.0 eq.), and 1,4-dioxane (50 mL). The system was evacuated and refilled with N2. The reaction mixture was heated at 80 C. for 5 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified on silica-gel column eluting with 80:1 dichloromethane/methanol to afford 128a as a yellow solid (992 mg, 50%). MS: [M+H]+ 405.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Young, Wendy B.; US2013/116245; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference 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.

Cyclopropanecarboxamide (58.7g, 690 mmol) in 1,4-Dioxane (1600 ml) was added 2-bromoacetyl bromide (59.9 ml, 690 mmol) at room temperature and stirred for 4h at 600C. The reaction mixture was concentrated to dryness. The residue was dissolved in EtOAc and carefully washed with satd. NaHCObeta, water then with brine solution, dried over Na2SO4 and concentrated to get N-(2- bromoacetyl) cyclopropanecarboxamide(138 g, 670 mmol, 97 % yield) as an off white solid. This material was used without purification. ESI-MS :m/z 208.0 (M+2H)+.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); A1;,
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. 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(4-Fluorophenyl)-N,N-dimethylacrylamide

General procedure: The dihydro-6H-quinolin-5-one (3a-v) were synthesized based on aliterature method as following: aryl and heteroaryl methylketones(1a-k, 5.23 mmol) were treated with dimethylformamide-dimethylacetal(DMF-DMA) (20.92 mmol) in refluxing xylene for 7 h to form beta-enaminones (2a-k), and reacted with cyclohexane-1,3-dione/5,5-dimethylcyclohexane-1,3-dione (0.16 g, 1.2 mmol) ammonium acetate(2.0 mmol) in 2-propanol (5 mL) were added CeCl3·7H2O (0.2 mmol),NaI (0.2 mmol) and refluxed for 4 h (monitored by TLC). The reactionmixture was cooled to room temperature; a solid precipitate was filteredand washed with cold 2-propanol. The combined solvent wasevaporated, and the crude residue obtained was subjected to columnchromatography (hexane: ethyl acetate) to obtain dihydro-6H-quinolin-5-one derivatives (3a-v) as solids in very good yields.

According to the analysis of related databases, 75175-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kantevari, Srinivas; Krishna, Vagolu Siva; Marvadi, Sandeep kumar; Sridhar, Balasubramanian; Srilakshmi Reshma, Rudraraju; Sriram, Dharmarajan; Surineni, Goverdhan; Bioorganic Chemistry; vol. 96; (2020);,
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. 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

A mixture of 2-(4-fluoropiperidin-l-yl)acetic acid(239 mg, 1.48 mmol), HATU (619 mg, l.63mmol) and DIPEA (524 mg, 4.44 mmol) in DCM (10 mL) and DMF(lOmL) was stirred at room temperature for 0.5 h. Then tert- butyl 4-aminophenethylcarbamate (350 mg, 1.48 mmol) was added and the reaction was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as yellow solid (400 mg, 71.3% yield). ‘H NMR (500 MHz, DMSO- d6) d: 10.38 (s, 1H), 7.50 (d, J= 8.3 Hz, 2H), 7.18 (t, J= 8.5 Hz, 2H), 6.87 (d, J= 5.5 Hz, 1H), (0881) 4.92 (d, J= 52.6 Hz, 1H), 3.95 (dd, J= 34.1, 9.3 Hz, 1H), 3.11 (dd, J= 13.9, 6.5 Hz, 5H), 2.81 (d, .7= 79.7 Hz, 1H), 2.65 (t, J= 7.4 Hz, 2H), 2.20 – 1.99 (m, 4H), 1.91 (s, 1H), 1.36 (s, 10H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 94838-59-2.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics