Tag: M.W=100-200

2675-89-0, A common compound: 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

EXAMPLE 18; N,N-Dimethylaminocarbonylmethyl 3-Aminosulfonyl-5-butylamino-4- phenoxybenzoate (Bumetanide N,N-Dimethylglycolamido Ester); [0481] Bumetanide (1.2g, 3.29 mmol) was dissolved in dimethylformamide (DMF, 10 mL) and 2- chloro-N,N-dimethylacetamide (410 muL, 3.9 mmol) was added followed by triethylamine (0.70 mL) and sodium iodide (545 mg, 3.6 mmol). The reaction was heated to 50C for 10 hours, TLC and LC/MS indicated the reaction was complete. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate, water, and brine and dried over anhydrous magnesium sulfate. The ethyl acetate was removed under reduced pressure and the product was purified via flash chromatography on silica gel to yield 685 mg (60%) of pure N,N- dimethylaminocarbonylmethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate.

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-Chloro-N,N-dimethylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROTHERAPEUTICS PHARMA, INC.; WANAKSI, Stephen; PARTRIDGE, John, J.; COLLINS, Stephen; WO2010/85352; (2010); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

102-93-2, 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. 102-93-2 name is 3-Phenylpropanamide, 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.

DCM (20 mL) was added to a flask containing Lawesson?s reagent (2.022 g, 5.00 mmol). 3-Phenylpropanamide (1 .492 g, 10.00 mmol) was dissolved in DCM (20 mL), added tothe suspension, and stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and purified by column chromatography (DCM) to afford the title compound (1 .07 g 1H NMR (500 MHz, ODd3) O 7.30 (t, 2H), 7.24 – 7.21 (m, 3H), 3.12 (t, 2H), 2.95 (t, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Phenylpropanamide, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLUM, Francesca; CARR, James Lindsay; SHAH, Pritom; DEL MAR JIMENEZ QUESADA, Maria; FARRE GUTIERREZ, Irene; (213 pag.)WO2016/124938; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 609-66-5, name is 2-Chlorobenzamide, molecular formula is C7H6ClNO, 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. 609-66-5

General procedure: (Diacetoxyiodo) benzene (5 mmol, 1.61g) and NaHSO4.H2O (1mmol, 0.138g) were stirred for 10-15 min, at room temperature in aqueous solution of acetonitrile (5 ml water and 5 mlacetonitrile). In this reaction mixture benzamide (1mmol) was added and stirring was continuing till reaction goes to completion (TLC). After completion of reaction, the reaction mixture was quenched with water and further extracted with chloroform (3¡Á10 ml). The combined chloroform layers were washed with water (3¡Á20ml) dried over Na2SO4, and concentrated on rota-evaporator to get the crude residue. The residue was further purified by column chromatography on silica gel using ethyl acetate: hexane (1:9) as an eluent to afford pure benzoquinone.

The chemical industry reduces the impact on the environment during synthesis 2-Chlorobenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sasane, Kulbhushan A.; Telvekar, Vikas N.; Synthetic Communications; vol. 44; 4; (2014); p. 468 – 473;,
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 3984-14-3 as follows. 3984-14-3

Step 16: Synthesis of N-[17-[2-(3-isopropylpyrazo]-l-yl)-7-methoxy-8-methylquinolin- 4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.Cf’6]octadec-7-ene-4- carbonyl](dimethylamino)sulfonamide (29).; A mixture of 27 (181 mg, 0.29 mmol) and CDI (117 mg, 0.72 mmol) in dry THF (15 mL) was heated at reflux under nitrogen for 50 min. LCMS analysis showed one peak of the intermediate 28, which if needed, can be isolated by column chromatography or can be reacted with the appropriate sulfonamide in a one- pot reaction. The reaction mixture was cooled down to room temperature and dimethylaminosulfonamide (98 mg, 0.79 mmol) was added. Then, DBU (141 mg, 0.92 mmol) was added and the reaction mixture was heated to 550C. After 12 h, the solvent was evaporated, and the residue partitioned between AcOEt and acidic water (pH = 4). The organic layer was EPO dried (Na2SO4) and evaporated under reduced pressure to give a crude material, which was purified by column chromatography (AcOEtZCH2Cb, 25:75) to give 70 mg (33 %) of the target compound 29 as a white powder: m/z = 736 (M+H)+. 1H NMR (CDCl3): 1.20-1.50 (m, 10H), 1.60- 1.75 (m, IH), 1.79-1.91 (m, 2H), 1.92-2.03 (m, IH), 2.19-2.48 (m, 3H), 2.52-2.63 (m, 5H), 2.89-2.96 (m, 7H), 3.03 (s, 3H), 3.04-3.14 (m, IH), 3.35-3.42 (m, 2H), 3.97 (s, 3H), 4.60 (dt, J = 13.2 Hz, J = 2.2 Hz, IH), 5.05 (t, / = 10.4 Hz, IH), 5.26-3.35 (m, IH), 5.64-5.70 (m, IH), 6.26 (s, IH), 6.32 (d, J = 2.5 Hz, IH), 7.11-7.15 (m, IH), 7.30 (s, IH), 7.95 (d, / = 9.1 Hz, IH), 8.69 (d, / = 2.5 Hz, IH), 10.6 (br s, IH).

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14925; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 14433-76-2, name is N,N-Dimethylcapramide, I believe this compound will play a more active role in future production and life. 14433-76-2

Lambda/,Lambda/-Dimethylhexanamide (1.5g, 10.6mmol) was slowly added to an initially stirred mixture of phosphorus trichloride (2.8ml, 32.2mmol) and phosphorous acid (1.15g, 14.0mmol). The mixture was heated at 7O0C for 2h. After cooling the excess phosphorous trichloride was decanted off and the residue hydrolyzed by the careful addition of plenty of water. This mixture was left to stir for at least 2h, filtered, and the filtrate evaporated to dryness under reduced pressure. The precipitate was taken up in 20ml of water and heated at 1000C for 1h, followed by filtration of the hot solution. The water was evaporated and the desired product was isolated as a colorless solid (1.64g, 54%). 1H NMR (300MHz, D2O): delta = 0.83 (t, J =6.26Hz, 3H), 1.27 (tt, J = 3.50, 7.24Hz, 4H), 1.50 (qd, J = 7.04, 6.98, 8.70Hz, 2H), 1.98 -2.04 (m, 2H), 3.03 (s, 6H)ppm. 13C NMR (75MHz, D2O): delta = 13.22, 21.58, 23.00, 28.93,31.54, 42.07, 69,18ppm. 31P NMR (121MHz, D2O): delta = 4.66ppm. HRMS: m/z calcd. for CaH22NO6P2: 290.0917, found: 290.0904.

The chemical industry reduces the impact on the environment during synthesis 14433-76-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HUMBOLDT-UNIVERSITAeT ZU BERLIN; RHEINISCH-WESTFAeLISCHE TECHNISCHE HOCHSCHULE AACHEN (RWTH); ARENZ, Christoph; ROTH, Anke Gundula; UHLIG, Stefan; DRESCHER, Daniela; WO2011/23624; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, Adding some certain compound to certain chemical reactions, such as: 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 402-46-0.

General procedure: A general method for preparing (4,6-diaryl-tetrahydropyridin-3-yl) (aryl) methanone 4 includes the following steps: In a 10 mL sealed tube, aryl propynol (0.10 mmol),Solvent (0.50 1.00mL), acid (0.01 0.04mmol) and chalcone derivative (0.10 0.20mmol), heated and reacted under reflux conditions. The reaction was monitored by TLC. After the arylpropynol reaction was completed, Add amine compounds (0.10 0.20mmol) and carry out the reaction under reflux conditions. The reaction duration is about 9 ~ 11h, then add water to the reaction solution to quench the reaction, add ethyl acetate to extract the organic phase, and use the obtained organic phase for It was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and then concentrated on a rotary evaporator. The resulting concentrated solution was purified by column chromatography.

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 402-46-0.

Reference:
Patent; Shanghai Institute of Technology; Yin Yan; Zhang Qinglin; Zhang Hua; Guo Huifeng; Pan Wanyong; Pei Keke; (18 pag.)CN110407739; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common compound: 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 67442-07-3

To a THF solution of (RS)-1-bromo-2-mehyloxy-3-(1-methyloxyheptyl)benzene (2, 6.3 g, 20 mmol) obtained in the second step was added dropwise 2M isopropylmagnesium chloride (20 mL). 2-Chloro-N-methyloxy-N-methylacetamide (5.5 g) was added thereto, and the mixture was stirred at room temperature. To the reaction solution was added aqueous hydrochloride acid solution, followed by extraction with ethyl acetate. After the solvent was distilled off, the residue was purified by silica gel chromatography to obtain 2.80 g of a compound (3). NMR (CDCl3) delta ppm: 7.58 – 7.61 (m, 1H), 7.51 – 7.54 (m, 1H), 7.22 – 7.27 (m, 1H), 4.72 (dd, 2H, J = 20.8 Hz, 15.9 Hz), 4.54 (dd, 1H, J = 8.1 Hz, 4.8 Hz), 3.78 (s, 3H), 3.22 (s, 3H), 1.14 – 1.77 (m, 10H), 0.84 – 0.90 ( m, 3H)

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, 67442-07-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shionogi&Co., Ltd.; EP2184279; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 3984-14-3, name is N,N-Dimethylsulfamide, 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 3984-14-3. 3984-14-3

EXAMPLE 10 8-cyclohexyl-N-[(dimethylamino)sulfonyl]-1,1a,2,12b-tetrahydro-1a-[[(cis)-2,6-dimethyl-4-morpholinyl]carbonyl]-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxamide. A 2M solution of oxalyl chloride (0.1 mL, 0.2 mmol) in CH2Cl2 was added dropwise to a solution of rel-8-cyclohexyl-1a-[[(cis)-2,6-dimethyl-4-morpholinyl]carbonyl]-1,1a,2,12b-tetrahydro-11-methoxy-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (54 mg, 0.1 mmol) in CH2Cl2 (10 mL) containing one drop of DMF. The reaction mixture was stirred at rt. for 2 h, afterwhich it was concentrated and dried under high vacuum. The resultant residue was dissolved in THF (10 mL) and a solution of N,N-dimethylsulfonamide (24.8 mg, 0.2 mmol) and DIPEA (0.052 mL, 0.3 mmol)) in THF (2 mL) was added. This was followed by the addition of DMAP (10 mg), after which the reaction mixture was stirred at rt. for 10 min, and then at 50 C. overnight. It was then concentrated and the residue purified by preparative reverse phase HPLC to afford the title compound as a white solid, (19.0 mg, 31% yield). MS m/z 649 (MH+), Retention time: 3.685 min; 1H NMR (500 MHz, CD3OD) delta ppm. Compound was observed to exist as inter-converting rotamers, as evidenced from the compound’s NMR spectrum.

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 N,N-Dimethylsulfamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/60565; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

14433-76-2, 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 14433-76-2 as follows.

(0084) The hydrogenolysis of N,N-dimethyldecylamine works best with a 1:2 molar ratio of [Ru(triphos-(OMe)2)TMM] and B(C6F5)3. Thus, when N,N-dimethyldecylamine (1.0 mmol) was reacted at 160 C. under an atmosphere of H2 (100 bar) with [Ru(triphos-(OMe)2)TMM] (10 mumol) and 2 mol % B(C6F5)3, a conversion of 99% of the amide was observed. The reaction produced 3% decanol and 97% dimethyldecylamine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 14433-76-2, and friends who are interested can also refer to it.

Reference:
Patent; Eastman Chemical Company; KLANKERMAYER, Juergen; WESTHUES, Stefan; LEITNER, Walter; HEMBRE, Robert Thomas; (11 pag.)US2019/345178; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

53297-70-4, 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. 53297-70-4, name is 4-Amino-3-methylbenzenesulfonamide, A new synthetic method of this compound is introduced below.

The compounds in Table 2 below were prepared in accordance with the procedures set forth in Example 1, Step 3 using either [(1-mesityl-1H-tetrazol-5-yl)thio]acetic acid (prepared as described in Example 1, Steps 2 and 3) or the appropriate counterpart and the appropriate amine in place of 2-chloro-3-aminopyridine.

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; MERCK & CO., INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2005/115147; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics