Month: August 2021

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 98-64-6 as follows. Application In Synthesis of 4-Chlorobenzenesulfonamide

General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 °C, and acidified to pH 1 with addition of HCl aqueous solution (10percent), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 .x. 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).

According to the analysis of related databases, 98-64-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Yin; Qiu, Ke-Ming; Lu, Xiang; Liu, Kai; Fu, Jie; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4730 – 4738;,
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Synthetic Route of 17641-08-6, 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. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To the appropriate Schiff bases of isatin (10 mmol) in8-10 cm3 of anhydrous DMF, K2CO3 (15 mmol) was addedand stirred at room temperature for 1 h. After completion of1 h, the solution turned red brown in color. Appropriatechloroanilides (10 mmol) and KI (2 mmol) were then addedto this solution drop wise and heated at 60 C for 5.5-9 h.After conforming the end of reaction by TLC (ethyl acetate:n-hexane 30:70), the mixture was poured into ice cold water.Precipitated crude product was filtered and washed thoroughlywith cold water (3 9 200 cm3). Compounds wererecrystallized from ethanol/water mixture (1:1). Reactiontimes, melting points, and yields are depicted in Table 1.

The synthetic route of 2-Chloro-N-(3-methoxyphenyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Debnath, Biplab; Ganguly, Swastika; Monatshefte fur Chemie; vol. 147; 3; (2016); p. 565 – 574;,
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Reference of 35303-76-5, The chemical industry reduces the impact on the environment during synthesis 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, I believe this compound will play a more active role in future production and life.

A solution of 4-(2-aminoethyl)benzenesulfonamide (80 mg, 0.40 mmol), AcOH (0.05 mL) and di-tert-butyl 4-(2-bromoacetamido)-4-(3-(tert-butoxy)-3- oxopropyl)heptanedioate (447 mg, 0.81 mmol) in DCE (20 mL) was stirred at 80 °C for 30 min under nitrogen. The reaction mixture was cooled to 0 °C, and treated with NaBH(QAc)3 (0,254 g, 1 ,2 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by biotage over silica gel to afford the desired product (322 mg, 63percent). NMR (400 MHz, DMSO-d6) 7.77 (s, 2 H), 7.64 (d, J – 8.0 Hz, 2 H), 7.23 (s. 2 H), 7.21 (d, J = 8.4 Hz, 2 H), 7.01 (s, 2 H), 6.80 (s. 2 H), 4.57 (s. 4 H), 3.61 (s, 4 H), 2.79-2,62 (m, 4 H), 2,09 (t, J = 8.0 Hz, 12 H), 1.76 (t, J = 8.0 Hz, 12 H), 1.32 (s, 54 H); MS (ESI), 636.5 (M/2+H)+.

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, 4-(2-Aminoethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MOLECULAR INSIGHT PHARMACEUTICALS; BABICH, John, W; ZIMMERMAN, Craig; JOYAL, John; LU, Genliang; HILLIER, Shawn; MARESCA, Kevin, P; MARQUIS, John; WO2013/103813; (2013); A1;,
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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. 437998-34-0, name is 2-Amino-3-bromobenzamide, A new synthetic method of this compound is introduced below., SDS of cas: 437998-34-0

General procedure: 2-Aminobenzamides (1 mmol) and 1,1-dichloro-2-nitroethene (1.2 mmol) were added to 5 mL of water in a 25 mL round-bottom flask. Then stirred at corresponding temperature and corresponding reaction time, after completion, the product precipitated from the reaction mixture and can be easily separated by filtration, then give the pure products.

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; Zhu, Fengjuan; Song, Runjiang; Li, Shen; Shao, Xusheng; Synlett; vol. 27; 14; (2016); p. 2167 – 2170;,
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Synthetic Route of 830-43-3, The chemical industry reduces the impact on the environment during synthesis 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, I believe this compound will play a more active role in future production and life.

A solution of l-[3-cyano-5-(isopropoxycarbonyl)-6-methylrhoyridin-2-yl]azetidine-3- carboxylic acid (0.091 g, 0.3 mmol), DIPEA 0.074 g, 0.6 mmol) and TBTU (0.039 g, 0.3 mmol) in leq. DCM/ 1 eq .DMF (2 mL) was added to sulfonamide^ .4 mmol), e.g. 4- (trifluoromethyl)benzenesulfonamide. The reaction mixture was stirred for 48h followed by addition of TBTU (0.013 g, 0.1 mmol). After 2Oh the solvents were removed in vacuo. The crude reaction mixture was added NaHSO4 (2 mL, IM) and due to differences in solubility between products DCM and DCM/ethyl acetate was used for extraction. The organic phase was isolated and the solvents were removed in vacuo. The crude material was purified using preparative HPLC (see below for details) in order to isolate the desired product, e.g. isopropyl 5-cyano-2-methyl-6- {3-[({ [4-(trifiuoromethyl)phenyl]sulfonyl}amino)carbonyl]azetidin- 1 – yl}nicotinate.

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, 4-(Trifluoromethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2007/8140; (2007); A1;,
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Some common heterocyclic compound, 78191-00-1, name is N-Methoxy-N-methylacetamide, molecular formula is C4H9NO2, 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. HPLC of Formula: C4H9NO2

A suspension of 6-bromo-3-isopropyl[1 ,2,4]triazolo[4,3-a]pyridine hydrochloride (1.00 g, 3.62 mmoi) in THF (18.0 mL) was charged with a positive stream of nitrogen and cooled to 0 0C. The resulting suspension was then treated with commercially available solution of isopropylmagnesium chloride in diethyl ether (2.0 M THF solution, 3.5 mL, 7.0 mmol). The internal temperature of the reaction was not allowed to exceed 0 0C. The resulting dark solution was allowed to stir for 1 hour and then the reaction was treated with N-methoxy-N-methyl acetamide. After 4 hours, the reaction was quenched with 100 mL of saturated ammonium chloride solution and was extracted with ethyl acetate (3 X 250 mL). The resulting organic extract was Na2SO4 dried, filtered, and concentrated in vacuo to a residue that was directly subjected to normal phase silica chromatography (60 % ethyl acetate, 30 % hexanes, 10 % MeOH) to furnish a gum (743 mg, 85 %). 1H NMR (300 MHz, O4-MeOH) delta 9.02 (s, 1 H), 7.87 (dd, J= 9.7, 1.5 Hz, 1 H), 7.68 (dd, J= 9.6, 1.1 Hz, 1 H), 3.72 (septet, J = 6.8 Hz, 1 H), 2.68 (s, 3H), 1.51 (d, J= 6.8 Hz1 6H); LC/MS C-18 column, tr = 0.48 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50 0C). ES-MS m/z 204 (M+H). ES-HRMS m/z 204.1158 (M+H calcd for C11H14N3O requires 204.1131).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 78191-00-1, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/18735; (2006); A2;,
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Reference of 263349-73-1, 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 263349-73-1 as follows.

EXAMPLE 342: 3-fluoro-4-(6-(trifluoromethyl)-lH-indazol-4- yl)benzenesulfonamide [0976] To a 5 mL vial equipped with a magnetic stir bar were added 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-lH-indazole (40 mg, 0.128 mmol), 4-bromo-3- fluorobenzenesulfonamide (39.1 mg, 0.154 mmol), aqueous saturated sodium bicarbonate (0.274 mL, 0.513 mmol), PdCl2(dppf) (9.38 mg, 0.013 mmol), and dioxane (2 mL) to give an orange suspension. The vial was sealed and then heated in a microwave reactor at 140C for 30 minutes. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-60% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a white solid (13.7 mg, 22.6%). 1H NMR (400 MHz, DMSO-<) delta ppm 7.50 (s, 2 H), 7.53 (s, 1 H), 7.75-7.80 (m, 1 H), 7.92-7.94 (m, 1 H), 8.02 (s, 1 H), 8.06 (dt, J=8.02, 1.29 Hz, 1H), 8.21 (t, J=1.64 Hz, 1 H), 8.40 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci4H9F4N302S, 360.0; found 360.1. According to the analysis of related databases, 263349-73-1, the application of this compound in the production field has become more and more popular. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (2013); A1;,
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These common heterocyclic compound, 127033-74-3, name is N-(3-Methoxyphenyl)cinnamamide, 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: N-(3-Methoxyphenyl)cinnamamide

In a 1000 mL reaction flask, 60 g of N- (cinnamoyl) -3-methoxyaniline was charged,100 g of anhydrous aluminum trichloride,500 mL of anhydrous chlorobenzene,Heating to 120 ,After refluxing for 2 hours,The reaction solution was poured into 500 mL of ice water,Produce a lot of hydrochloric acid gas,After stirring for 2 hours,The filter cake was added to 500 mL of methanol to recrystallize,To give 39 g of a light red solid,Yield: 60%Purity 94.5%.

The synthetic route of N-(3-Methoxyphenyl)cinnamamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Nuoxing Pharmaceutical Technology Co., Ltd.; Jiang Kaiyuan; Zheng Zhiwei; Sun Weihong; (6 pag.)CN107098855; (2017); A;,
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Reference of 610302-03-9, 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 610302-03-9 as follows.

Step B – Synthesis of Intermediate Compound 6c To a solution of compound 6b (4.1 mg, 19.04 mmol), 4-nitrobenzoic acid (3.82 g, 22.85 mmol), and PPh3 (9.9g, 38.1 mmol) in THF (60 ml) was added DEAD (6.03 mL, 38.1 mmol) at 0C. The reaction mixture was then stirred at 25C for 16 h, quenched with water (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic phase was washed with water (100 mL x 2), dried over Na2S04, and concentrated in vacuo. The residue was purified using column chromatography (Si02, Petroleum ether: EtOAc = 10: 1 to 5: 1) to provide compound 6c (1.3 g, 81% yield) as a white solid.

According to the analysis of related databases, 610302-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; NEELAMKAVIL, Santhosh F.; WALJI, Abbas; MARCO, Christine Ng Di; COLEMAN, Paul; WAI, John; RAHEEM, Izzat T.; HU, Lihong; PENG, Xuanjia; WO2015/39348; (2015); A1;,
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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. 3792-04-9, name is 2-Chloro-N-(2-(trifluoromethyl)phenyl)acetamide, A new synthetic method of this compound is introduced below., SDS of cas: 3792-04-9

Chrysin (1) (100 mg, 0.39 mmol), 2-chloro-N-(2-(trifluoromethyl)phenyl)acetamide (6) (98 mg,0.41 mmol) and anhydrous potassium carbonate (112 mg, 0.81 mmol) were dissolved in DMF (4 mL).The reaction mixture was stirred at 75 C for 9 h, then, it was poured into water (30 mL). Afterfiltering off the precipitate, the filtrate was diluted with saturated NaCl solution (30 mL) andextracted with DCM (4 x 30 mL). The combined organic layer was washed with water (30 mL), driedover MgSO4 and concentrated in vacuo. The filtered precipitation and the crude product obtained byextraction were purified separately with preparative TLC (DCM : MeOH = 60 : 1). Combining thepure products 50 mg (28 %) of compound 20 was isolated as a white solid. M.p.: 210-212 C. TLC(DCM : MeOH = 60 : 1); Rf = 0.71.

The synthetic route of 3792-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mayer, Szabolcs; Keglevich, Peter; Abranyi-Balogh, Peter; Szigetvari, Aron; Dekany, Miklos; Szantay, Csaba; Hazai, Laszlo; Molecules; vol. 25; 4; (2020);,
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