Tag: M.W=100-200

Synthetic Route of 13621-50-6, The chemical industry reduces the impact on the environment during synthesis 13621-50-6, name is Ethyl 3-amino-3-thioxopropanoate, I believe this compound will play a more active role in future production and life.

Ethyl 2-amino-4-isopropyl-6-thio-5-cyano-1,4-dihydropyridine-3-carboxylate (IV). 1.0 g (10 mmol)of cyanothioacetamide II and a solution of sodiumethylate prepared from 0.23 g (10 mmol) of sodiumand 15 mL of anhydrous ethanol were added to a solution of 0.91 mL (10 mmol) of isobutyral Ia in15 mL of anhydrous ethanol at 20C. The reactionmixture was stirred during 5 min, then 1.5 g (10 mmol)of CH-acid III was added, and the mixture was stirredduring 30 min and incubated during 48 h. Next, themixture was diluted with 10% hydrochloric acid to pH5 upon stirring and incubated at room temperatureduring 48 h. The formed precipitate was filtered offand washed sequentially with water, ethanol, andhexane (Tables 1 and 2). Mass spectrum, m/z (Irel, %):266 (100) [M – 1]+.

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 3-amino-3-thioxopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dyachenko; Karpov; Dyachenko; Russian Journal of General Chemistry; vol. 85; 5; (2015); p. 1063 – 1068; Russian Journal of General Chemistry; vol. 85; 5; (2015); p. 1063 – 1068,6;,
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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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

To a stirred suspension of Intermediate B (3.00 g, 14.08 mmol) in THF (50 ml_) was added chlorotrimethylsilane (3.57 mL, 28.16 mmol). The mixture was stirred at rt for 3 h. The mixture was placed in a water ice bath and 2-propylmagnesium chloride (2M in THF; 29.6 mL, 59.14 mmol) was added dropwise. The suspension immediately went into solution. The ice bath was removed and the mixture was stirred at rt for 3 h. The mixture was placed in an ice bath and 2- chloro-AA-methoxy-AA-methylacetamide (2.91 g, 21.12 mmol) was added in one portion. The ice bath was once again removed and the reaction was stirred at rt for 16 h. The reaction was poured over a mixture of ice and saturated, aqueous ammonium chloride (250 mL). The mixture was allowed to warm to rt and EtOAc (200 mL) was added. The undissolved solid was collected by filtration to afford 636 mg (21percent) of the desired product. The layers of the filtrate were separated and and the aqueous phase was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to dryness. The crude solid was triturated with EtOAc to provide an additional 1.62 g (55percent) of the desired product, for a combined yield of 2.26 g (76percent). ES-MS m/z 211.47 [M+H]+, HPLC RT (min) 1.67.

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; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
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Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 918538-04-2, name is Pyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione, 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 918538-04-2, SDS of cas: 918538-04-2

To a co-solvent of diisopropylethylamine (4.5 mL) and toluene (2OmL) was added intermediate 5? (1.6g, 10.4mmoL) and POC13 (2.94mL). The mixture was heated at 120C in a sealed tube for 20h, then poured into an ice-cooled saturated sodium bicarbonate solution (5OmL). Stirred for 1 5mm. Extracted with CH2C12 (3x5OmL). Combined organic layers were washed with brine (lx5OmL), dried (Mg504) and concentrated. Column chromatography purification (50-100% CH2C12 in hexanes) afforded the desired dichloride 1 as a light brown solid (1.2g, 86% yield). ?H NMR (CDC13): oe 6.98(1H, m), 7.05 (1H, m),7.86 (1H, m); MS: 187 (M+W).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; SUZHOU KINTOR PHARMACEUTICALS, INC.; GUO, Chuangxin; TONG, Youzhi; (160 pag.)WO2017/219800; (2017); 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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H8ClNO

Example 5.2Preparation of Cy-O-CH2-CONMe2 (Product 2-R1=Cy)Cyclohexanol (12.2 g, 0.11 mol) and toluene (42.2 g) are loaded In a 250 mL reactor. The temperature of this mixture is brought to 30 C. Soda (5.6 g, 0.14 mol) is then introduced with portions of about 2 g. The reaction mixture is mechanically stirred. After maintaining the stirring for ten minutes at 30 C., chlorodimethylacetamide (11.6 g, 0.09 mol) is added dropwise directly into the mass within 0.5 hour. The reaction medium is maintained with stirring at 30 C. for 5 hours. Distilled water is introduced until the totality of the salts are dissolved (about 30 mL). The organic phase is recovered and the solvents are distilled under partial pressure and the desired product is obtained, 12 g, with a yield of 72%.

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; Vidal, Thierry; Guglieri, Massimo; Jentzer, Olivier; US2012/302791; (2012); 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. 156731-40-7, name is 1-(Boc-amino)-3-butene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H17NO2

3-chloro-perbenzoic acid (3 equiv) is added to an ice-cooled solution of t-butyl but-3-enyl- carbamate (1 equiv) in CH2CI2 in an inert atmosphere and stirred at 40 for 3 hours. The mixture obtained is cooled to 5 and quenched with saturated aq. sodium bisulfite solution. After extraction with CH2CI2, the combined organic layers obtained are washed 3 times with saturated aq. potassium carbonate solution, dried, filtered and concentrated.(+/-)-t-butyl (2-oxiranyl-ethyl)-carbamate is obtained.

According to the analysis of related databases, 156731-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/48771; (2007); A1;,
Amide – Wikipedia,
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Electric Literature of 2835-68-9, 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. 2835-68-9, name is 4-Aminobenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture of 3-chloro-5-[(3-hydroxy-4-methylphenyl)amino]-4H-1,2,6-thiadiazin-4-one (7) (53.9 mg, 0.200 mmol), Pd[3,5-(F3C)2C6H3]3 (5.3 mg, 1.25 mol %), DPEPhos (5.3 mg, 5 mol %), powdered dry K2CO3 (66.4 mg, 0.480 mmol) and 3-aminobenzamide (30.0 mg, 0.220 mmol) was added dioxane (5 mL). The stirred suspension was then deaerated by bubbling of Ar through it for 5 min and then heated at reflux under Ar until complete consumption of the starting thiadiazine (TLC, 2 h). The mixture was cooled to ca. 20 C, then adsorbed onto silica and chromatographed (n-hexane/acetone, 50:50) to give the title compound 1 (63.1 mg, 85%) as orange needles, m.p. 297-298 C (from THF)

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

Reference:
Article; Asquith, Christopher R. M.; Godoi, Paulo H.; Cou ago, Rafael M.; Laitinen, Tuomo; Scott, John W.; Langendorf, Christopher G.; Oakhill, Jonathan S.; Drewry, David H.; Zuercher, William J.; Koutentis, Panayiotis A.; Willson, Timothy M.; Kalogirou, Andreas S.; Molecules; vol. 23; 5; (2018);,
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Application of 869494-16-6, These common heterocyclic compound, 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-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.

In a microwave vial a solution of 3 -chloro-4-(6-fluoropyridin-3 -yl)-6-( i-methyl-i Hpyrazol-4-yl)pyrazolo[i,5-a]pyridine (Intermediate P9; 5 mg, 0.015 mmol) and tert-butyl 3,6- diazabicyclo[3.i.i]heptane-6-carboxylate (9.1 mg, 0.046 mmol) in DMSO (0.2 mL) was subjected to microwave irradiation at 130 °C for 5 h and then at 150 °C for 6 h. The reaction mixture was cooled to ambient temperature and then directly purified by reverse phase chromatography (5-95percent ACN/water) to afford the title compound (2.6 mg, 34percent yield). ?H NIVIR (CDC13) 8.51 (d, 1H), 8.34 (d, 1H), 7.88 (s, 1H), 7.76 (s, 1H), 7.65 (m, 2H), 7.12 (d, 1H), 6.62(d, 1H), 4.33 (m, 2H), 4.20 (m, 2H), 3.98 (s, 3H), 3.55 (m, 2H), 1.45 (d, 2H), 1.38 (s, 9H).

Statistics shows that tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate is playing an increasingly important role. we look forward to future research findings about 869494-16-6.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); 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. 132289-57-7, name is N,2-Dimethoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 132289-57-7

B) 1-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-methoxyethanone To a mixture of 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene (25.0 g) and N,2-dimethoxy-N-methylacetamide (15.4 g) and tetrahydrofuran (400 mL) was gradually added 1.6M n-butyllithium/hexane solution (72.4 mL) under a nitrogen atmosphere at -78 C. The reaction mixture was stirred under a nitrogen atmosphere at -78 C. for 20 min. After stirring, the mixture was neutralized with 0.1M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (15.7 g). 1H NMR (300 MHz, CDCl3) delta 3.50 (3H, s), 4.63 (2H, s), 7.42 (1H, ddd, J=8.6, 7.3, 1.5 Hz), 7.75-7.81 (1H, m), 7.83 (1H, dd, J=10.2, 1.9 Hz).

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 132289-57-7.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); A1;,
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Amide – an overview | ScienceDirect Topics

Synthetic Route of 2895-21-8, 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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) The compound 1 (500 mg), the compound 2 (677 mg) and sodium carbonate (529 mg) were suspended inacetonitrile (10 mL), and the reaction mixture was stirred for 18 hours at 60 C. The reaction mixture was cooled toroom temperature, and then diluted with ethyl acetate, washed with water and brine, and dried over anhydroussodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silicagel column chromatography (eluent: ethyl acetate-methanol; gradient: 100:0-95:5) to give the compound 3 (711 mg)as a colorless solid.MS (APCI) 300 [M+H]+

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

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; USHIROGOCHI, Hideki; SASAKI, Wataru; ONDA, Yuichi; SAKAKIBARA, Ryo; AKAHOSHI, Fumihiko; (158 pag.)EP3135668; (2017); A1;,
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63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, 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 C9H12N2O3

4-bromo-ethyl – benzoic acid ethyl ester (4.0g, 16.46mmol) was added in THF (30mL) solution of N- ethylpiperazine (3.76g,32.92mmol), The reaction mixture was stirred at room temperature for 16 hour. The reaction mixture was diluted withwater and the product was extracted with ethyl acetate. The combined organiclayers were washed with water, brine, Na 2SO 4dry. The solvent was removed togive 4.61g of crude 4- (4-ethyl-piperazin-1-yl-methyl) – benzoic acid ethylester (100% yield). The LAH (0.792g, 20.86mmol)was added to a dry 3-necked flask, THF (60mL) under cooling. Was slowly added under cooling 4- (4-ethyl-piperazin-1-yl-methyl) – benzoic acid ethyl ester(4.61g, 16.69mmol) in THF (10mL) was added. After the addition was complete,the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled to 0 deg.]C, was added 10% NaOH solution, then water was added. The organic layer wasseparated, the aqueous layer was extracted with ethyl acetate. The combinedorganic layers were washed with water, brine, Na 2SO 4dry. The solvent wasremoved to give 2.78gof crude (4- (4-ethyl-piperazin-1-yl-methyl) phenyl) -methanol, 78% yield.anhydrous CH2Cl2 cooled to -78 deg.] C containingthe (100 mL) 3-necked flask was added oxalyl chloride(1.8g, 14.25mmol) and DMSO (1.85g, 23.76mmol),at -78 deg.] C and the mixture was stirred for 15 minutes. It was added at -78 (4- (4- ethyl-piperazin-1-yl-methyl) phenyl) – methanol(2.78g, 11.88mmol) in CH2Cl 2The (10 mL) was stirred at -78 1 hour. Was then added at -78 Et 3N (4.8g,47.52mmol). The reaction mixture was brought to room temperature. Water was added, the organiclayer was separated. The aqueous layer was extracted with CH 2Cl 2extraction.The combined organic layers were washed with water, brine, Na 2SO 4dry. Then, the solvent was removedto give crude 4- (4-ethyl-piperazin-1-yl-methyl)benzaldehyde (2.5g, 91%). 2-amino-4,6-dimethoxy – benzamide (150mg, 0.76mmol) and 4-(4-ethyl-piperazin-1-yl-methyl) benzaldehyde (177mg, 0.76mmol) in N , N- dimethylacetamide(10 mL) was added NaHSO 3(150mg,0.84mmol) and p-TSA (319mg, 1.68mmol), thereaction mixture was at 150 was heated for 5 hours. The reactionmixture was cooled to room temperature, water was added, the mixture was treated with NaHCO 3neutralize. The solventwas removed under reduced pressure to give the crude product, which waspurified by column chromatography to give 2- (4 -((4-ethyl-piperazin-1-yl) methyl) phenyl) -5,7 dimethoxy – quinazolin -4 (3H) -one (87mg, 27%), converted to the hydrochloride salt. Selected data: MS(ES) m / z: 409.11; MP278-280 (decomposition

The synthetic route of 63920-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP; HANSEN, H; (62 pag.)CN103319408; (2016); B;,
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