Month: February 2021

Reference of 360-64-5, The chemical industry reduces the impact on the environment during synthesis 360-64-5, name is 2-(Trifluoromethyl)benzamide, I believe this compound will play a more active role in future production and life.

Methyl S-chloropyrazine-2-carboxylate (879 mg), 2-trifluoromethylbenzamide (1.OS g), Cs2CO3 (2.31 g), xantphos (0.268 g), and Pd2(dba)3 (0.141 g) were stirred in dioxane (25.5 mL) under argon atmosphere at 80C for 6 hours. The mixture was cooled, and then AcOEt and water were added thereto and the mixture was stirred. Then, insoluble substances were filtered through Celite. The filtrate was separated, and the organic layer was washed with water and saturated brine, dried over anhydrous Na2 SO4, and filtered. The solvent was removed, and then the resulted residue was purified by column chromatography (Hexane/AcOEt). The resultant was confirmed as methyl S-[(2-(trifluoromethyl)benzamidojpyrazine-2-carboxylate (1.69 g) by 1H-NMR (CDC13MeOH (16.5 mL) was added thereto, and then thereto was added SN aqueous NaOH solution (4.1 mL) under ice cooling. The mixture was stirred at room temperature for 4 hours. The mixture was adjusted to pH=4 by addition of 5N HC1 (4.1 mL) and the resulted precipitate was filtered and dried at 60C to give5- [2-(trifluoromethyl)benzamidojpyrazine-2-carboxylic acid (1.56 g).

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, 2-(Trifluoromethyl)benzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KAN, Keizo; TAKUWA, Masatoshi; TANAKA, Hirotaka; FUJIWARA, Hideto; YAMABE, Hokuto; MATSUDA, Satoshi; OHDACHI, Kazuhiro; HANARI, Taiki; MENJO, Yasuhiro; URUSHIMA, Tatsuya; FUJITA, Shigekazu; (183 pag.)WO2019/4421; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 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 127828-22-2, Product Details of 127828-22-2

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate was then taken up in CH2Cl2 (20 mL) along with salicylic acid (576 mg, 4.17 mmol) and EDCI (905 mg. 4.72 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with CH2Cl2 (20 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by chromatography (9:1 CH2Cl2/MeOH) to afford tert-butyl 2-(2-(2-hydroxybenzamido)ethoxy)ethylcarbamate (450 mg, 33%). Mass calculated for C16H24N2O5: 324.17; found: [M+H]+=325.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82192; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 33045-52-2, 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. 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) 2-Methoxy-5-sulfamoylbenzoic acid. Methyl 2-methoxy-5-sulfamoylbenzoate(4.91g, 20mmol) was dissolved in methanol(30mL). 2N Aqueous sodium hydroxide(30mL, 60mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 2N hydrochloric acid, and the separated solid was filtered to give the title compound(4.55g, 98.3%) as a white solid. 1H-NMR(DMSO-d6): delta 3.89(3H, s), 7.30(1H, d, J=8.7Hz), 7.32(2H, s), 7.92(1H, dd, J=8.7, 2.7Hz), 8.09(1H, d, J=2.7Hz), 13.03(1H, br).

The synthetic route of Methyl 2-methoxy-5-sulfamoylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1512396; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 156731-40-7, name is 1-(Boc-amino)-3-butene, 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. Quality Control of 1-(Boc-amino)-3-butene

Intermediate 154. tert-butyl but-3-en-1 -yl(methyl)carbamate To a 0 C solution of tert-butyl but-3-en-1 -ylcarbamate (Intermediate 62, 840mg, 4.9mmol) in THF (20ml_) was added, under inert atmosphere, sodium hydride (216mg of a 60% dispersion in oil, 8.99mmol) and the reaction mixture was stirred at r.t. for 1 h before methyl iodide (3.05ml_, 49.0mmol) was added. The reaction mixture was heated to reflux and maintained at this temperature overnight. Ice was then added and the aquous phase was extracted with ethyl acetate (3 x 50ml_). The combined organic extracts were washed with brine, filtered and concentrated to dryness to afford the title compound as a colorless oil (893mg, 98%). 1 H NMR (300 MHz, cdcl3) delta 5.75 (dddd, J = 17.1 , 13.7, 6.8, 3.4 Hz, 1 H), 5.17 – 4.92 (m, 2H), 3.39 – 3.08 (m, 2H), 2.84 (s, 3H), 2.37 – 2.13 (m, 2H), 1 .45 (s, 9H).

The synthetic route of 1-(Boc-amino)-3-butene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; PUIG DURAN, Carlos; AIGUADE BOSCH, Jose; GUAL ROIG, Silvia; PRAT QUINONES, Maria; (149 pag.)WO2016/46390; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37045-73-1, name is 3-(Methylsulfonamido)aniline, 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 37045-73-1, Application In Synthesis of 3-(Methylsulfonamido)aniline

In a 1000 mL four-necked flask with mechanical stirring and a thermometer,Add 700g of water,Methanesulfonamidoaniline 149g(content 80%, 0.64 mol),Calcium carbonate 150g (1.50mol),Stir well and then as solution A,Transfered to the pipeline reactor by screw pump A,At the same time pumping liquid 1-chlorohexane 163g (1.35mol),Solution A and 1-chlorohexane are fed with screw pump A and screw pump B, respectively.The mass flow rate ratio of the control solution A to 1-chlorohexane was 6.1:1.0.The pipeline reactor has a pipeline reaction section providing a chemical reaction site, and the solution A and 1-chlorohexane are continuously reacted in the pipeline reaction section.Keep the temperature of the pipeline reaction section at 135 C,Control the residence time of the reaction solution to 10 min,Cooled, extracted with 800 mL of 2-methyltetrahydrofuran.The combined organic phases are concentrated under reduced pressure.Obtaining dialkylaminomethanesulfonanilide214.1g,97.6%,The yield was 94.5%.

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, 3-(Methylsulfonamido)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JIANGSU DIAN CHEMICAL CO LTD; Jiangsu Di’an Chemical Co., Ltd.; ZHEJIANG SHANYU TECH CO LTD; Zhejiang Shanyu Technology Co., Ltd.; TAO ANNI; Tao Anni; GUO HAIBIN; Guo Haibin; WEI BIN; Wei Bin; LI JIAN; Li Jian; ZHENG TUCAI; Zheng Tucai; XU XUMING; Xu Xuming; HU XIAOKUI; Hu Xiaokui; (6 pag.)CN108299250; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 758-96-3, name is N,N-Dimethylpropionamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C5H11NO

Weigh 6-methoxybenzothiazole (0.5mmol, 83mg), K2S2O8 (2mmol, 0.54g) and Eosin Y (0.01mmol, 6.5mg) in a 25mL Schlenk reaction tube, and then add N, N-dimethyl Propionamide (38mmol, 3.8g) was placed under a 20W power LED white light to react. The reaction was stirred at room temperature. The progress of the reaction was monitored by TLC. The reaction was completed after 24 hours. The reaction solution was concentrated to remove the solvent. Separation (eluent: petroleum ether / ethyl acetate with a volume ratio of 5: 1) gave a yellow oil, namely the derivative Il. Yield: 74%.

The synthetic route of 758-96-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Weng Jianquan; Xu Wenxiu; Dai Xiaoqiang; Liu Xinghai; (11 pag.)CN110432282; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, 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. Safety of R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide

EXAMPLES Example 1 Preparation of (R)-2-bromo-N- [2- (4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl] – acetamide) 1.0 g of (R)-2- (4-methoxyphenyl-3-aminosulfonyl-phenyl)-1-methylethylamine was dissolved in 50 ml of methylene chloride. 0.72 g (2.0 eq) of triethyamine was added to the resultant solution and cooled to 0 to 5C. Then, 1.44 g (2.0 eq) of bromoacetyl bromide was added dropwise to the resultant solution and stirred at 0 to 5C. After it was confirmed by HPLC that the starting materials were completely consumed, 100 ml of ethyl acetate and then 50 ml of 10% HCI were added to the resultant solution and stirred. The ethyl acetate layer was separated and washed with 50 ml of a 10% K2CO3 solution and dried over MgS04, and then, filtered and concentrated. The obtained concentrate was dissolved in ethyl acetate and recrystallized with hexane to obtain the title compound (1.2 g). Yield : 80.0% NMR (DMSO-d6) : 1.15 (3H, d), 2. 6-2. 8 (2H, m), 3.8 (2H, s), 3.90 (4H, s), 7.0 (2H, s), 7.1 (1H, d), 7.4 (1H, d), 7.6 (1H, d), 8.21 (2H, d). [a] 24D = + 5.0 (C=1, MeOH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 112101-81-2, its application will become more common.

Reference:
Patent; CJ CORPORATION; WO2005/56521; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 17400-34-9,Some common heterocyclic compound, 17400-34-9, name is Benzyl (3-aminopropyl)carbamate hydrochloride, molecular formula is C11H17ClN2O2, 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.

Intermediate 5 Benzyl N-r2-(pent-4-vnamido) propyll carbamate Pentynoic acid (0.267 g, 2.72 mmol) was added to a suspension of Z-propandiamine hydrochloride ( 1 g, 4 mmol), EDCI- HCI 767 mg, 4 mmol) a nd HOBt. H20 (540 mg, 4 mmol) in dry DCM (20 ml_) . The resulting mixture was cooled at 0C a nd TEA ( 1.12 ml_, 8 mmol) was added dropwise. The reaction mixture was stirred at 25C for 16h. The DCM solution was washed with NH4CI solution (20 ml_ x 2) and NaHC03 solution, the organic phase was filtered through a phase separator and evaporated to dryness to obta in the title compound as a white solid (800 mg) . The crude product was used in the next step without further purification . JH NMR (400 MHz, CDCI3) delta 7.41-7.31 (m, 5H), 6.20 (br s, 1 H), 5.27 (br s, 1 H), 5.12 (s, 2H), 3.34 (q , 2H), 3.27 (q , 2H), 2.59-2.52 (m, 2H), 2.42 (t, 2H), 2.02 (br s, 1 H) . UPLC-MS Rt=0.76; m/z (ES+) : 289 [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 Benzyl (3-aminopropyl)carbamate hydrochloride, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; S?RENSEN, Morten, Dahl; DI FABIO, Romani; POZZAN, Alfonso; CATALANI, Maria, Pia; BLADH, Haakon; FELDING, Jakob; WO2013/124286; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 636-76-0, name is 3-Sulfamoylbenzoic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Sulfamoylbenzoic acid

To 3-aminosulfonylbenzoic acid (4.0g), N,N-dimethylformamide (53 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.8 g), 1-hydroxybenzotriazole (2.7 g), N,O-dimethylhydroxylamine hydrochloride (1.9 g), and triethylamine (2.8 ml) were added under ice cooling and the mixture was stirred at room temperature for 12 hours. A potassium hydrogensulfate aqueous solution and ethyl acetate were added to the reaction solution and the mixture was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was successively washed with distilled water, saturated sodium hydrogencarbonate aqueous solution, and saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2). To the obtained N-methoxy-N-methyl-3-aminosulfonylbenzamide (1.8 g), tetrahydrofuran (36 ml) and ethyl magnesium bromide (0.89M tetrahydrofuran solution, 41 ml) were added under ice cooling, the mixture was stirred at room temperature for 3 hours, then saturated ammonium chloride aqueous solution and ethyl acetate were added to reaction solution, the mixture was separated, then organic layer was successively washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1). To the obtained 3-propionylbenzenesulfonamide (0.97 g), ethanol (2.5 ml), sodium acetate (0.56 g), and hydroxylamine hydrochloride (0.35 g) were added and the mixture was stirred at 90C for 3 hours. Ethyl acetate and water were added to the reaction solution, the mixture was separated, then the organic layer was successively washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained 3-(N-hydroxypropanimidoyl)benzenesulfonamide was used instead of the starting material compound of Reference Example 109, that is, 1-(4-aminophenyl)propan-1-on oxime, for the similar procedure as with Reference Example 109 to obtain the title compound. NMR (DMSO-d6): delta8.50-8.36(3H, br), 7.92(1H, s), 7.83(1H, d, J=7.5Hz), 7.71-7.60(2H, m), 7.42(2H, s), 4.33-4.21(1H, br), 2.00-1.70(2H, m), 0.75(3H, t, J=7.4Hz) MS: 215(M+H)+

The synthetic route of 636-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asubio Pharma Co., Ltd.; Daiichi Sankyo Company, Limited; EP2025672; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 121492-06-6, These common heterocyclic compound, 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, 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 128: N-{5-[3-(4-Bromo-2-fluoro-phenylamino)-pyridin-4-yl]- [1 ,3,4]oxadiazol-2-yl}-N’-methyl-ettiane-1 ,2-diamine; Step 1 : 5-[3-(4-Bromo-2-fluoro-phenylamino)-pyridin-4-yl]-3H-[1 ,3,4]oxadiazol-2-one (example 19, 100mg, 0.277mmol) was dissolved in ethanol (3ml), N-(2-aminoethyl)-N – methylcarbamic acid ^-butylester (96rng, 0.554mmol) was added and the mixture was stirred for20min at 1500C in a microwave oven. The volatiles were removed to give the crude compound, which was used in the next step.Step 2: Dry dichloromethane (5ml) was added to the product derived from step 1 followed by triphenylphosphine (113rng, 0.429mmol), triethylamine (58mul, 0.416mmol) and carbon tetrachloride (107mul, 1.11 mmol). The mixture was heated at 1000C for20min in a microwave oven, the volatiles were removed and the crude material was purified by preparative HPLC to give 87mg (62/yield) of the Boc-protected title compound. The material was treated with 4N HCI in dioxane (4ml) for 1h at ambient temperature and the volatiles were removed to give the pure title compound. LC-MS (method V): rt = 1.94rnin; m/z [M+ H]+ 407/409.

The synthetic route of 121492-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/45514; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics