Author: tianli

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. 3144-09-0, name is Methylsulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3144-09-0

Reference Example 42 To a mixture of methane sulfonamide (1.96 g), triethylamine (3.2 mL), 4-(dimethylamino)pyridine (252 mg), and dichloromethane (30 mL) was added a mixture of di-tert-butyl dicarbonate (5.17 g) and dichloromethane (40 mL) at room temperature for 30 minutes. The mixture was concentrated after stirring for 2 hours, and the residue was distributed with ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with water, dried and concentrated. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl methylsulfonyl carbamate (2.44 g). 1H-NMR (300 MHz, CDCl3) delta: 1.52 (9H, s), 3.28 (3H, s).

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1553074; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112101-81-2, A common compound: 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, 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 3;Preparation of Tamsulosin HydrochlorideTamsulosin Hydrochloride is also prepared according to this example by first repeating the initial reaction, cooling, and filtering steps of Example 2 to produce the filtrate at 0 C.Instead of using ammonia, the filtrate is then alkalinized with DIEA until a pH of 8.5 is obtained, and the desired product is extracted with 2 x 50 mL of AcOEt. The combined organic layers are then extracted twice with 50 mL of water at pH 6 (adjusted with HCl). The EPO aqueous phases are combined and the pH is again adjusted to 8.5 with DDEA, and the product is then extracted with 2 x 25 mL of AcOEt.The combined organic phases obtained from the extractions are dried over Na2SO4 and the solvent is evaporated to obtain 3.28 g of crude tamsulosin. The content of byproduct as determined by HPLC method 1 was 0.261% (area percentage).The residue is dissolved in ethanol (32 mL) and 1.65 mL (7.76 mmol) of ethanol HCl 4.7 N are charged. Then, the mixture is cooled down to 0 C and the solid is collected by filtration, washed with ethanol and dried in vacuum at 60 C until constant weight to yield 2.17 g (4.87 mmols, 26% molar yield) of tamsulosin hydrochloride. By subsequent analysis, the content of by-product (formula (VE)) by HPLC method 1 at this stage is 0.08 area %.The tamsulosin hydrochloride thus obtained is further purified by repeating twice the following procedure: treating with 29 mL of ethanol at 78 C, stirring for 30 minutes, cooling to 0 C, filtering, washing with ethanol and then drying at 60 C in vacuum until constant weight. After drying, 1.98 g of tamsulosin hydrochloride are obtained (4.45 mmols, 91% partial molar yield). (Assay: 100.21%; IR: matches the standard; melting point: 227.4-229.3 C; chemical purity: 99.31 area % by HPLC method 1; XRD (20), see Figure 1; content of byproduct (formula (VII)) by HPLC method 1 : 0.02 area %)

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, R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICHEM, S.A.; WO2007/4077; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

109903-35-7, Adding a certain compound to certain chemical reactions, such as: 109903-35-7, name is 4-Amino-N-methylbenzenemethanesulfonamide, 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 109903-35-7.

To the [NITRO-LH-INDAZOLE-3-CARBOXYLIC] acid (1 equiv. ) of Example 63A in DMF (0.3 M) was added EDC (1.2 equiv. ), HOBT (1.2 equiv. ), NMM (1.2 equiv. ) and then 4- [METHYLSULPHAMOYLMETHYL-PHENYLAMINE] (1.3 equiv. ) at room temperature. The reaction was heated to [70 C] for 2 hours and then stirred at room temperature for 48 hours. Water was added to the reaction mixture and the precipitated product was filtered. The solid was washed with water, then a small volume [OF MEOH,] and then dried in a vacuum oven to leave a yellow solid.

According to the analysis of related databases, 109903-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2004/14864; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

749927-69-3, A common heterocyclic compound, 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, molecular formula is C8H7BrFNO, 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.

Step 14-bromo-N-methyl-2- 14-(2,2,2-trifluoroethyl)piperazin-1-ylj benzamide4-Bromo-2-fluoro-N-methylbenzamide (1.17 g, 5.04 mmol) was dissolved in dimethyl sulfoxide (8 mL). 1-(2,2,2-Trifluoroethyl)piperazine (1.69 g, 10.05 mmol) and K2C03 (1.5511.22 mmol) were added, and the reaction mixture was heated to 120 C for 17 hours. The reaction mixture was partition between water (100 mL) and ethyl acetate (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over Mg504, filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate, Rf=0.51) to give the titled compound (1.60 g, 83%). ?H NMR (300 MHz, DMSO-d6) 5 ppm2.75-2.80 (m, 7H), 2.92-2.95 (m, 4H), 3.24 (q. J=10.3 Hz, 2H), 7.25-7.28 (m, 2H), 7.48 (d, J=8.5 Hz, 1H), 8.58(q, J=4.4 Hz, 1H); MS(ESI+) m/z 380 & 382 (M+H).

The synthetic route of 749927-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; SCANIO, Marc; BUNNELLE, William; KOENIG, John Robert; DRIZIN, Irene; PLIUSHCHEV, Marina; COWART, Marlon; WO2015/112445; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

22227-26-5, 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. 22227-26-5, name is 3,5-Bis(trifluoromethyl)benzamide, A new synthetic method of this compound is introduced below.

A, 1560 g of intermediate 2,6.24 L of ~ N ‘N-dimethylformamide was charged into a 50 L autoclave, and the reaction was cooled to 12 ¡ã C; B, adding sodium hydroxide in batches, And control the reaction system temperature does not exceed 15 ¡ã C, Add to continue stirring 20min; C, the reaction system is cooled to 10 ¡ã C, adding the magnesium chloride hexahydrate to the reaction system, the temperature of the reaction system is 10 ~ 15 D, the reaction system to room temperature, stirring 4h; E, with hydrochloric acid to adjust the reaction system pH to 2.2, and the body reaction system temperature below 20 ¡ã C; F was added to the reaction system by the addition of 5 L of methyl tert-butyl ether, and the layers were separated and then extracted with methyl tert-butyl ether (2.5 L X). The organic layers were combined and washed with saturated sodium chloride (2.5 LX 2); G, concentrated, the residue was added to petroleum ether beating and dried at room temperature to give 1931 g of intermediate 5;H, 1.9 kg of intermediate 5 and 8.9 kg of methanol were charged into a 50 L autoclave, and the reaction was cooled to 10 ¡ã C; I, dropping formylhydrazide into the reaction system; J, the reaction system to cool to 0 ¡ã C; K, 666 g of ethyl formate was added dropwise and the temperature was controlled at 0 to 5 ¡ã C; L, the reaction system temperature to 90 ~ 95 ¡ã C, and at this temperature for 6h; M, the reaction system to cool to 35 ~ 40 ¡ã C, and then to the reaction system by adding 28L of water; N, the addition of methyl tert-butyl ether 12L extraction, standing after the separation, the water phase and then 10L methyl tert-butyl ether extraction; combined organic layer, with saturated sodium chloride (6L X 2) O, the solvent was removed, the crude product was beaten with methylene chloride 3L at room temperature, filtered and dried to give 1.28 kg of intermediate 4 with a liquid phase purity of 98.6percent.

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; Guangzhou Wenhao Biological Technology Co., Ltd.; Chen Xinying; Xu Liang; Liu Wenzhong; (6 pag.)CN106831617; (2017); A;,
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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide, This compound has unique chemical properties. The synthetic route is as follows., 2895-21-8

. Then filtered and purified by silica column chromatography eluting with 0-100% EtOAc in Pet. Ether to give 2-[2-chloro-4-[1-methyl-5-[(1-tetrahydropyran-2-ylindazol-5-yl)amino]-1,2,4-triazol-3-yl]phenoxy]-N-isopropylacetamide (108 mg, 0.20 mmol, 44% yield). LC-MS (ES+, Method F): 3.76 min, m/z 524.1 [M+H]+

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (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. 402-46-0, name is 4-Fluorobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., 402-46-0

Ar under the protection, A solution of 1-methyl-4 – ((3-methoxyphenyl) amino) -7-chloro-1H-indole- (1001 ^, 0 ¡¤ 30mmo 1) Dissolved in dry DCM, Followed by addition of HATU (172 mg, 0.45 mmo 1) DMAP (18 mg, 0.15 mmo 1) And TEA (92 mg, 0.90 mmol), After stirring, 4-fluorobenzenesulfonamide (80 mg, 0.45 mmol) was added and incubated overnight at room temperature, After the reaction, the solvent was distilled off, Followed by dilute hydrochloric acid, washed with water, combined EA layer, column separation of light yellow green solid (75mg, 51.4%)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Shen Zhufang; Bie Jianbo; Mu Yongzhao; Chen Hualong; Liu Lvnan; Zhou Jie; Li Caina; Cao Ran; Huan Yi; Sun Shujuan; (258 pag.)CN107098846; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1943-79-9, 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. 1943-79-9, name is Phenyl methylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a DMF suspension of sodium hydride (containing 40% mineral oil, 430 mg), 4-(1H-5-indolyloxy)-2-pyridinamine (2.253 g, CAS No.417722-11-3) described in International Publication No. WO02/32872 was slowly added under a nitrogen atmosphere at room temperature. The reaction mixture was stirred for 10 minutes at room temperature and then cooled in an ice-cold water bath, followed by addition of phenyl N-methylcarbamate (1.587 g). The reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was added to ethyl acetate and water and partitioned between them to separate the organic layer. The resulting organic layer was washed sequentially with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then evaporated to remove the solvent. The residue was crystallized from ethyl acetate, and the precipitated crystals were collected by filtration and dried under ventilation to give N1-methyl-5-(2-amino-4-pyridyl)oxy-1H-indolecarboxamide (2.163 g) as a light brown crystal. The physical property data of the resulting compound are as shown below. 1H-NMR (CDCl3) delta (ppm): 3.09 (d,J=4.8 Hz,3H), 4.36 (m,2H), 5.49 (m,1H), 5.92 (d,1H,J=2.0 Hz), 6.30 (dd,J=6.0,2.0 Hz,1H), 6.61 (d,J=3.6 Hz,1H), 7.07 (dd,J=8.8,2.4 Hz,1H), 7.30 (d,J=2.4 Hz,1H), 7.45 (d,J=3.6 Hz,1H), 7.92 (d,J=6.0 Hz,1H), 8.17 (d,J=8.8 Hz,1H).

The synthetic route of 1943-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US2006/241038; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2, 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. 127828-22-2 name is tert-Butyl (2-(2-aminoethoxy)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.

To a chilled solution (-15 C) of 2 (1.41 g, 4.61 mmol) in THF (20 mL) was added N-methylmorpholine (NMM; 0.51 mL, 4.61 mmol) and subsequently isobutylchloroformate (IBCF; 0.61 mL, 4.61 mmol) under N2 atmosphere. After 5 min, a solution of 1 (0.857 g, 4.19 mmol) in THF (10 mL) was added dropwise at the same temperature, and the mixture was stirred for 30 min at the same temperature and then at room temperature for 1 h. After removing the solvent in vacuo, the residue was dissolved in ethyl acetate (50 mL). The organic phase was washed with 5% NaHCO3 (30 mL ¡Á 2), 5% citric acid (30 mL ¡Á 3), saturated NaCl solution (30 mL ¡Á 1), successively and dried over anhydrous MgSO4. After removal of the solvent in vacuo, the residue was subjected to flash chromatography on silica gel using a mixture of chloroform/methanol (100:1) as an eluent to provide 3 as a pale yellow solid (1.67 g, 80.6%) melting at 128-129 C. 1H NMR (CDCl3): delta 1.44 (9H, s, Boc), 3.17-3.51 (10H, overlapped, CH2), 4.76-4.78 (1H, dd, CH), 6.89 (1H, d, NH), 7.35-7.37 (2H, d, aromatic), 8.14-8.16 (2H, d, aromatic). ESI-MS (M+Na)+: m/z 515, found: 515. Anal. Calcd for C20H27N4O7F3: C, 48.78; H, 5.53; N, 11.38. Found: C, 48.46; H, 5.30; N, 11.21.

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:
Article; Suzuki, Hiroyuki; Kanai, Ayaka; Uehara, Tomoya; Guerra Gomez, Francisco L.; Hanaoka, Hirofumi; Arano, Yasushi; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 978 – 984;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 7341-96-0, name is Propiolamide, 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 7341-96-0. 7341-96-0

The imine (0.2mmol), rhodium acetate (0.002mmol), Molecular sieve (300 mg) and the mixture is dissolved 1.5 ml dichloromethane solvent, into mixed solution 1, in 20 C stirring for 10 minutes. Then the propargyl amide (0.24mmol) and inter-methoxyphenyl diazo acetic acid methyl ester (0.24mmol) dissolved in 1.0 ml methylene chloride solvent, into solution 2. The solution 2 for 20 C lower, in 1 hour for adding and mixing the solution in the injection pump 1. The reaction mixture is purified by rapid column chromatography, to obtain the pure product, its structure is formula (c) is shown. The yield is 90%, dr value is equal to the 95:5. The product of the1As shown in Figure 5, H NMR schematic view thereof13C NMR schematic view as shown in Figure 6.

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 Propiolamide.

Reference:
Patent; EAST CHINA NORMAL UNIVERSITY; HU, WENHAO; WU, YONG; WANG, WENKE; TANG, MIN; (29 pag.)CN106146334; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics