Month: March 2021

Electric Literature of 91893-69-5, A common heterocyclic compound, 91893-69-5, name is 2-Amino-N,N-dimethylethanesulfonamide hydrochloride, molecular formula is C4H13ClN2O2S, 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.

General procedure: General procedure C: A mixture of amine hydrochloride (1.73 mmol), NaOH (0.10 g, 2.59 mmol) and ethanol (50 mL) was stirred and heated to reflux for 1 h. Then gossypol acetic acid (0.50 g, 0.86 mmol) was added and the reaction liquid continued to reflux for 5 h. The reaction mixture was cooled to room temperature and then the resulting solid was filtered, washed with ethanol and then recrystallized with pyridine and ethanol or chloroform and ethanol to give the desired gossypol derivatives. Data for 19: General procedure C; yellow solids; yield, 61.0%; mp, 235-237C; 1H NMR (400MHz, CDCl3) delta 13.47-13.37 (m, 2H), 9.64 (d, J=12.2Hz, 2H), 7.89 (s, 2H), 7.59 (s, 2H), 5.61 (s, 2H), 3.95 (dd, J=11.8, 6.5Hz, 4H), 3.76-3.66 (m, 2H), 3.26 (t, J=6.5Hz, 4H), 2.88 (s, 12H), 2.11 (s, 6H), 1.55-1.50 (m, 12H); 13C NMR (100MHz, CDCl3) delta 173.51, 162.80, 149.02, 146.96, 132.25, 129.22, 128.09, 118.37, 115.97, 114.40, 103.70, 48.57, 45.17, 37.28, 27.45, 20.34, 20.29, 20.07; HRMS (ESI) calcd for C38H49N4O10S2 (M-H)- 785.2896, found 785.2873.

The synthetic route of 91893-69-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Ling; Li, Zheng; Wang, Kailiang; Liu, Yuxiu; Li, Yongqiang; Wang, Qingmin; Bioorganic and Medicinal Chemistry; vol. 24; 3; (2016); p. 474 – 483;,
Amide – Wikipedia,
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Some common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, molecular formula is C10H15NO2S, 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 4-(tert-Butyl)benzenesulfonamide

General procedure: To a solution of 12 3,4-diphenyl-1H-pyrrole-2,5-dione 4b (4.96mmol) in 83 CH3CN (20mL), 84 K2CO3 (4.96mmol), 85 TBAB (0.5mmol) and 16 1,4-dibromobutane (19.84mmol) were added and the mixture was stirred at 45¡ãC overnight. Solvent was evaporated to dryness, 86 water (50mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and solvent evaporated to dryness. 17 8 was obtained by a silica gel column chromatography. The solution of 88 BBr3 (1M, 9.47mmol) in anhydrous 89 CH2Cl2 was added to compound 17 8 (3.94mmol) in 20mL anhydrous CH2Cl2 under nitrogen atmosphere at ?78¡ãC. The mixture was stirred at ?78¡ãC for 1h. The temperature rised to 0¡ãC, 10mL 90 H2O was added and the resulting solution was stirred for 0.5h and extracted with ethyl acetate. Collected organic layers were washed with brine and dried over anhydrous Na2SO4, and solvent was evaporated to dryness to afford compound 18 9, a yellow solid with sufficient purity to be used without further purification. To a solution of 18 9 (1.86mmol) and 84 K2CO3 (2.28mmol) in 10mL 92 acetone, methyl bromoacetate was added. The reaction proceeded reflux overnight and was added 30mL 86 water. Then, the mixture was extracted with ethyl acetate and dried over anhydrous Na2SO4. The residue was purified by a silica gel column chromatography to give 93 10. K2CO3 (1.76mmol), KI (1.32mmol), substituted aromatic sulfonamide (1.32mmol) and compound 10 were added to 2mL CH3CN. The mixture was stirred reflux overnight, and solvent was concentrated, H2O (12mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and evaporated. 11 was obtained by a silica gel column chromatography. 1M aqueous solution of LiOH (1.11mmol) was added to the solution of compound 11 (0.742mmol) in 4mL THF at ?5¡ãC. The mixture was stirred at ?5¡ãC until complete by TLC and adjusted to pH 5 by 1M HCl. The resulting mixture was extracted with diethyl ether, and the organic layer was wash by brine and dried over anhydrous Na2SO4. The solution was evaporated to afford compound 12. To a solution of glycylglycine methyl ester hydrochloride (0.81mmol) and DIPEA (1.62mmol) in 5mL CH3CN, 12 (0.67mmol), HOBt (0.81mmol) and EDCl (0.81mmol) were added at 0¡ãC. The mixture proceeded at 50¡ãC overnight, diluted with CH2Cl2 and washed with brine. The organic layer was dried over anhydrous Na2SO4 and evaporated. Compound 13 was obtained by the silica gel column chromatography. For the synthesis of 14a-j, Et3N (0.866mmol) and LiCl (0.94mmol) were added to the solution of compound 13 in 5mL CH3CN: H2O (95: 5) at 0¡ãC. The solution was adjusted to pH 5 by 1M HCl and evaporated by CH2Cl2. Combined organic layer was washed by brine, dried over anhydrous Na2SO4 and concentrated. The resulting residue was triturated with ethyl acetate and filtrated to give target compound 14a-j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6292-59-7, its application will become more common.

Reference:
Article; Yuan, Xinrui; Xia, Yineng; Lu, Peng; Zhu, Lijuan; Zhong, Yuejiao; Wang, Yubin; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1435 – 1447;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 104863-65-2, name is N-Methoxy-N-methylpropionamide, 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 104863-65-2, name: N-Methoxy-N-methylpropionamide

The reaction formula of this embodiment is as follows:In a 25 ml reaction flask, add compound 1a (0.3 mmol, 0.1561 g), compound 2i (15 mmol, 1.7573 g), water (30 muL), DCM (5 mL) to dissolve the above materials, and stir the reaction at 60 C. The reaction time is 3 h. After the reaction was completed, the solvent was removed by spin-drying, and the residue was subjected to flash column chromatography (PE: EA = 20: 1) to obtain pure product 3ai (0.0534 g) with a yield of 76%.

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, N-Methoxy-N-methylpropionamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xuzhou Medical University; Wu Nan; Xu Zhou; Mi Jiajia; Li Chuang; Yuan Changyong; Zheng Yan; (15 pag.)CN110668937; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 108-13-4, name is Malonamide, molecular formula is C3H6N2O2, 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 108-13-4

General procedure: An example of the preparation of the amide intermediate was carried out. Blocking the reaction vessel (when the amide intermediate is at a boiling point under normal pressure, etc.At or below the reaction temperature TB below) or to keep the reactor open (when the boiling point of the amide intermediate at normal pressure is higher than the reaction temperature TB described below), stirring is continued (600 r / min), The reaction temperature is changed to TB, and after maintaining the reaction temperature TB for TD hours, the reaction vessel is closed and connected to a vacuum pump, so that the degree of vacuum in the reaction vessel reaches 20-50 mbar (adjusted according to the type of nitrile product) to distill off As a nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic resonance spectroscopy and elemental analysis to characterize the obtained nitrile product. The specific reaction conditions and characterization results are shown in Tables A-6, A-7, A-8, A-9 and A-10 below. These characterization results indicate that the obtained nitrile product has an extremely high purity (99% or more).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-13-4, its application will become more common.

Reference:
Patent; Sinopec Yangzi Petrochemical Co., Ltd.; Sinopec Corporation; Sun Hailong; Gao Yilong; Wei Yanyu; Chen Xinhua; Miao Jun; Li Na; Kan Lin; Bai Jiye; Chen Shaohui; Yang Aiwu; Xu Yuexing; (32 pag.)CN105016941; (2018); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, 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: 2-Chloro-N-methylacetamide

Step 3. Preparation of 2-[4-(5-cyano-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide (4)4-Methoxy-3-(piperidin-4-yloxy)benzonitrile hydrochloride salt (3, 28.36 g, 95.82 mmoles), 2-chloro-N-methylacetamide (12.37 g, 114.98 mmoles) and potassium carbonate (33.11 g, 239.55 mmoles) were suspended in acetonitrile (161.36 g). The reaction mixture was heated at reflux for 3 hours. The reaction mixture was cooled to 20 C. and water (386.26 g) was charged. The reaction was heated to 75 C. and the volume reduced by distillation. Upon cooling crystallisation occurred. The resulting solid was isolated by filtration, washed twice with water (77.25 g and 128.75 g) and then dried to give the title compound (27.95 g, 94% yield); 1H NMR (400 MHz, DMSO-d6) delta ppm 1.68 (m, 2H) 1.91 (m, 2H) 2.29 (m, 2H) 2.61 (d, J=4.7 Hz, 3H) 2.67 (m, 2H) 2.88 (s, 2H) 3.83 (s, 3H) 4.41 (tt, J=8.3, 4.0 Hz, 1H) 7.11 (d, J=8.4 Hz, 1H) 7.40 (dd, J=8.4, 1.9 Hz, 1H) 7.47 (d, J=1.9 Hz, 1H) 7.68 (q, J=4.7 Hz, 1H); Mass Spectrum: m/z (M+H)+ 304.2.

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

Reference:
Patent; ASTRAZENECA AB; US2009/286982; (2009); 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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, A new synthetic method of this compound is introduced below., COA of Formula: C8H18N2O2

tert-Butyl methyl(2-(3-(5-(trifluoromethyl)-1 ,2,4-oxadiazol -3- yI)benzamido)ethyl)carbamate 3-(5-(Trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzoic acid (1 .24 g, 4.8 mmol), EDCI(922 mg, 4.8 mmol), HOBt (648 mg, 4.8 mmol), and DIPEA (774 mg, 6mmol) were added to a solution of crude tert-butyl (2-aminoethyl)(methyl)carbamate in DCM (5OmL). The reaction mixture was stirred at room temperature overnight. Water (20 mL) was added to the mixture and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (40 mL x3). The combined organic solvents was washed with brine (30 mL), driedover Na2SO4. After removal of solvents, the crude compound was purified by flash column (EtOAc: PE = 2:1) to provide tert-butyl methyl(2-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamido)ethyl)carbamate as a white solid (1.1 g, yield 66%). MS (ESI) m/z: Calculated for C18H21F3N404: 414.15; found: 437 (M-f-Na).

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

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; BALOGLU, Erkan; WO2013/6408; (2013); 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. 5202-85-7, name is 2-Amino-5-chlorobenzamide, A new synthetic method of this compound is introduced below., Formula: C7H7ClN2O

General procedure: 2-aminobenzamide 2 (1.0 mmol) was added to a suspensionof the catalyst 5 (2.1 mmol/g, 0.05 g, 0.1 mmol) inCHCl3 (10 mL) and stirred for 10 min, followed by N-Bocimines 1 (1.1 mmol) and stirred at -15 C for 24-36 h, thereaction was ascertained by TLC. When the reaction wascompleted, the mixture was filtered and washed severaltimes with CHCl3. The filtrate was concentrated and purifiedby silica gel chromatography to obtain pure product.

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:
Article; Zhang, Baohua; Shi, Lanxiang; Guo, Ruixia; Catalysis Letters; vol. 145; 9; (2015); p. 1718 – 1723;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

98-64-6, name is 4-Chlorobenzenesulfonamide, 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

General procedure: To a mixture of PS-tet-Cu(II) 2 (0.05 g) and arylboronicacid (0.7 mmol) in water (5 mL), K2CO3(1 mmol), sulfonamide(0.7 mmol) and water (5 mL) was added and the mixture was vig-orously stirred for the appropriate times under reflux conditions.After completion (as monitored by TLC), the catalyst was filteredand the reaction mixture was cooled to room temperature. Theresulting product was filtered and purified by recrystallizationusing ethyl acetate and n-hexane to afford N-arylated product. Allcompounds were compared with the corresponding compoundsprepared by the reported procedure [4,23?40]. All compounds wereknown and were characterized by spectral analysis or meltingpoints.1H NMR data of some compounds are given below.

The synthetic route of 98-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nasrollahzadeh, Mahmoud; Rostami-Vartooni, Akbar; Ehsani, Ali; Moghadam, Majid; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 123 – 129;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 38267-76-4, name is tert-Butyl ethylcarbamate, 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 38267-76-4, HPLC of Formula: C7H15NO2

[00753] Step F: 5-chloro-3-(4-(2-fluorophenoxy)cyclohex-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (0.75 g, 1.58 mmol) and tert-butyl ethylcarbamate (0.92 g, 6.33 mmol) were dissolved in dioxane (16 mL) and dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphane (0.29 g, 0.63 mmol), sodium t-butoxide (0.30 g, 3.2 mmol) and Pd2dba3 (0.29 g, 0.32 mmol) were added and purged with nitrogen. The tube was sealed and heated to 100 C overnight, partitioned between EtOAc and water, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (10-30% EtOAc in hexanes) to afford tert-butyl ethyl(3-(4-(2-fluorophenoxy)cyclohex-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamate (615 mg, 66.7% 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, tert-Butyl ethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); 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. 79722-21-7, name is tert-Butyl benzyloxycarbamate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 79722-21-7

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue 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 79722-21-7.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics