Category: amides-buliding-blocks

Application of 224789-21-3, 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 224789-21-3 as follows.

Example 5 Preparation of 2-(2-ethoxy-5-chlorosulfonyl)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][ 1,2,4]triazine-4-one Chlorosulfuric acid (50ml)was added into a 100ml three-neck flask with a stirrer, 2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-one (31.2g (0.1mol))was added in batches under stirring in an ice bath. The reaction was exothermic and was performed for 12 hrs. The reaction solution was slowly poured into icy water (100g), a white solid was separated out, filtered, dried. A white solid (30g)was obtained with a yield of 76%.

According to the analysis of related databases, 224789-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; WANG, Jianping; WANG, Jianguo; EP2666776; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 112257-19-9, 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. 112257-19-9 name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, 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.

Step 6 tert-Butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate A mixture of 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde (21.5 g, 70.24 mmol, 1.00 equiv), tert-butyl N-methyl-N-(2-(methylamino)ethyl)carbamate (20 g, 106.23 mmol, 1.51 equiv) and NaBH(OAc)3 (29.8 g, 137.98 mmol, 1.96 equiv) in dichloroethane (300 mL) was stirred for 1 h at room temperature. The reaction was diluted with 300 mL of dichloromethane and then washed with 3*300 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-7percent methanol in dichloromethane to give 31 g (92percent) of tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate as a yellow oil. 1H NMR (300 MHz, CDCl3): delta 7.62 (s, 1H), 5.34-5.30 (m, 1H), 4.06-4.02 (m, 1H), 3.68-3.62 (m, 1H), 3.42-3.38 (m, 4H), 2.85 (s, 4H), 2.62-2.53 (m, 2H), 2.47-2.46 (m, 2H), 2.13-1.97 (m, 3H), 1.74-1.69 (m, 3H), 1.46 (s, 9H) ppm. LCMS (method A, ESI): RT=1.17 min, m/z=479.0 [M+H]+.

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

Reference:
Patent; Epizyme, Inc.; Mitchell, Lorna Helen; Shapiro, Gideon; Chesworth, Richard; Moradei, Oscar Miguel; US2014/288128; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 90-16-4, These common heterocyclic compound, 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, 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.

A solution of l,2,3-benzotriazin-4(3H)-one (commercially available, 1.0 equiv.), 2- chloromethyl-oxirane (4.0 equiv.) and potassium carbonate (4.0 equiv.) in methyl ethyl ketone was refluxed for about 16 hours. The reaction mixture was concentrated under vacuum; the residue was taken in water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography using mixture of ethyl acetate and hexane as eluent to form 3- (oxiran-2-ylmethyl)-l,2,3-benzotriazin-4(3H)-one. Yield: 75%

The synthetic route of 90-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/117760; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 5004-88-6, These common heterocyclic compound, 5004-88-6, name is 2-Amino-4,5-dimethoxybenzamide, 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.

To a stirred mixture of 4 g of 2-amino-4,5-dimethoxybenzamide and 200 ml of ether was added dropwise, e solution of 3.3 g of benzoyl isothiocyanate in 100 ml of ether over 15 minutes. After 24 hours, the solid was collected, giving 7 g of the desired product as white crystals, mp 204-207 C. (dec.).

Statistics shows that 2-Amino-4,5-dimethoxybenzamide is playing an increasingly important role. we look forward to future research findings about 5004-88-6.

Reference:
Patent; American Cyanamid Company; US5001157; (1991); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 5202-85-7, A common heterocyclic compound, 5202-85-7, name is 2-Amino-5-chlorobenzamide, molecular formula is C7H7ClN2O, 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.

An aromatic amine 1q-1 (0.20 mmol) and a platensimycin acid (0.10 mmol) were weighed.2-(7-Azobenzotriazole)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) (0.30 mmol) was added to the reaction flask and 1.0 ml was added.N,N-dimethylformamide, stirring at room temperature; slowly adding triethylamine (0.45 mmol), stirring for 12 hours, rotary evaporationSolvent to obtain a crude product, which is subjected to column chromatography to obtain a platensimycin analog2q-1, yield 46%.

The synthetic route of 5202-85-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Ha Yao Cihang Pharmaceutical Co., Ltd.; Duan Yanwen; Shen Ben; Huang Yong; Zhu Xiangcheng; Qiu Lin; Tian Kai; (39 pag.)CN107793388; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 618-48-4, name is 3-Chlorobenzamide, 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. Recommanded Product: 618-48-4

Then slowly raise the temperature, turn on the ultrasonic generator at the same time, control the ultrasonic frequency of 20KHz, the concentrated ultrasonic horn is directly immersed in the reaction liquid of the kettle body, and a large amount of energy is directly transmitted to the reaction medium.Effectively convert electrical energy into ultrasonic energy, and control the size of ultrasonic energy by changing the amplitude of the generator. Use a constant temperature system to make the material react at a constant temperature of 230 ~ 250 C for 2h, and then continue to increase the temperature, control the temperature of 250 ~ 270 C, and react for 2h. To generate a mixture containing m-chlorobenzonitrile, turn off the ultrasonic generator.Crude nitrile was distilled off from the mixture containing m-chlorobenzonitrile under reduced pressure, and the residue after distillation contained intermediate products (ammonium m-chlorobenzoate and m-chlorobenzamide) produced by the reaction, which were left in the ultrasonic thermostat and continued at the next feeding reaction.The crude nitrile is washed with water, filtered, dried and then distilled under reduced pressure to obtain the finished product. The content of m-chlorobenzonitrile measured by high performance liquid chromatography was 97.0%. Calculate the yield. Based on m-chlorobenzoic acid, the yield of finished m-chlorobenzonitrile is 92.5%.The wastewater produced by washing the crude nitrile with water contains available raw materials m-chlorobenzoic acid, the intermediate products ammonium m-chlorobenzoate, and m-chlorobenzamide. The water is recovered by distillation and concentration, and the intermediate products are recovered. After drying, During the secondary reaction, it was put into the reaction kettle as part of the raw materials to continue the reaction.

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

Reference:
Patent; Sanmenxia Huanyu Biochemical Technology Co., Ltd.; Duan Jingjie; Zhang Weimin; Liang Zhenxian; Wei Zhanyong; Tan Jing; Zhang Kun; Wang Xinyue; Wang Yan; Wang Zhiquan; (7 pag.)CN110467541; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16375-88-5, 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. 16375-88-5, name is N-(4-(Hydroxymethyl)phenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. (4-Acetamido)-phenylmethyl-4-nitrophenylcarbonate To a solution of 242.8 mg of p-nitrophenyl chloroformate in 5 mL of acetonitrile at 0 C. was added sequentially, 165.2 mg of 4-acetamidobenzyl alcohol and 0.13 mL of 4-methyl morpholine. The mixture was stirred for 24 hours and concentrated in vacuo. The residue was taken up in CH2 Cl2 and washed with 5% sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 320 mg of the title compound. TLC: Rf=0.23, 50% EtOAc/hexane.

The synthetic route of N-(4-(Hydroxymethyl)phenyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals, Incorporated; US5783701; (1998); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 579474-47-8, These common heterocyclic compound, 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, 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.

A solution of 0110-31 (200 mg, 0.4 mmol), TBTU (200 mg, 0.6 mmol), N1, Lambdaf2-diisopropylethane-l, 2-diamine (364 mg, 2.82 mmol), and tert-butyl 2-amino-4- fluorophenylcarbamate (0113-60) (90 mg, 0.4 mmol) in DMF (4 mL) and THF (2 mL) was stirred at r.t. for 3 hours. Then DMF and THF were removed under reduced pressure and the residue was dispensed in water and filtered to get the crude product. The crude compound was further purified by flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to afford pure product tert-butyl 2-(4- (4-(2-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-ylamino)-2- oxoethyl)phenoxy)butanamido)-4-fluorophenylcarbamate (150 mg, 54%) as a pale yellow solid. LCMS : 698 [M+ 1 ]+.

Statistics shows that tert-Butyl 2-amino-4-fluorophenylcarbamate is playing an increasingly important role. we look forward to future research findings about 579474-47-8.

Reference:
Patent; CURIS, INC.; QIAN, Changgeng; CAI, Xiong; ZHAI, Haixiao; WO2010/75542; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, molecular formula is C10H11F2NO4S, 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. Product Details of 1103234-56-5

Triethylamine (4.68 mL, 33.59 mmol) and diphenylphosphonic azide (3.73 mL, 16.79 mmol) were added to a solution of 2,6-difluoro-3-(propylsulfonamido)benzoic acid (4.078 g, 14.6 mmol) in THF (60 mL). The reaction mixture was stirred at room temperature for 3 hours and then warmed to 80C for 2 hours. Water (10 mL) was added, and the mixture was stirred at 80C for 15 hours. The reaction mixture was diluted with EtOAc (300 mL), and the organic layer was washed with saturated aqueous NaHC03 solution and brine. The solvent was removed under reduced pressure, and the residual purified via silica gel column chromatography eluting with 30/70 EtOAc/hexane to obtain 2.03 g (55%) of the title compound. 1H NMR (400 MHz, DMSO-d6) delta 9.32 (s, 1H), 6.90-^.80 (m, 1H), 6.51 (td, J=8.7, 5.5, 1H), 5.28 (s, 2H), 3.05-2.96 (m, 2H), 1.82-1.64 (m, 2H), 1.01-0.90 (m, 3H). LC/MS: w/z 251.1 [M+l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1103234-56-5, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); 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 406233-31-6 as follows. name: 4-Fluoro-3-nitrobenzenesulfonamide

General procedure: To an ice cold stirred solution of compound 4a-4u (1 eq) in anhydrousDCM (10 mL for 1 mmol of substrate), TEA (3 eq) was added dropwise and stirred for 10 min. Compound 5 (1 eq) was added slowly andstirred at RT for 16 h (precipitation was observed during the reactionprogress). TLC showed completion of reaction. The reaction mixturewas concentrated under reduced pressure. Water was added to thecrude material and stirred for 30 min. Obtained solid was filtered,washed with water and dried under vacuum. The solid was trituratedwith ethyl acetate, filtered and dried under high vacuum to affordcompound 6a-v.

According to the analysis of related databases, 406233-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kalisha Vali; Gundla, Rambabu; Singh, Om V.; Tamboli, Yasinalli; Di Cesare Manelli, Lorenzo; Ghelardini, Carla; Al-Tamimi, Abdul-Malek S.; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.; Bioorganic Chemistry; vol. 92; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics