Month: November 2020

3984-14-3, 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 3984-14-3 as follows.

EXAMPLE 19; (compound 64) (IC50=B*, EC50=E*)IS-cyclohexyl-N-zetadimethylaminosulfonylJ-YH-indoloftJ-aJftJbenzazepine- 10-carboxamide. A mixture of Example 15 (50 mg, 0.14 mmol), N5N- dimethylsulfamide (21 mg, 0.17 mmol), 4-(dimethylamino)pyridine (17 mg, 0.14 mmol), and l-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (40 mg, 0.21 mmol) in dichloromethane (1 mL) and DMF (1 mL) was stirred for 18 hours at 22 C. The mixture was poured into ethyl acetate and dilute aqueous acetic acid. The ethyl acetate layer was washed (water, brine), dried (Na2SO4), filtered, and concentrated. The residue was crystallized from ethyl acetate to provide the desired product (17 mg, 26% yield) as pale yellow crystals. ESI-MS m/z 358 (MH+); 1H NMR (300 MHz5 CDCl3) delta 1.20-2.30 (m, 10H), 2.81 (m, IH), 3.05 (s, 3H), 3.47 (m, 2H), 4.11 (m, IH,) 4.89 (s, IH), ,6.27 (m, IH), 6.80 (d, J=10.61 Hz, IH), 7.38 (m, 4H), 7.51 (m, IH), 7.89 (d, J=8.42 Hz, IH), 8.02 (s, IH), 8.75 (s, IH).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/92000; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, Adding a certain compound to certain chemical reactions, such as: 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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 6292-59-7.

Example 3: Preparation of propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5- (2-methoxy-phenoxy)-[2, 2′] bipyrimidinyl-4-yloxy]-ethyl ester compound of formula IV.A mixture of 4-tert butyl benzene sulfonamide (49.5g, 1eq), Potassium phosphate (123.8g, 2.5eq) dimethyl acetamide (500ml, 5vol) was heated to 40¡ãC and maintained for 30-60 minutes. Propionic acid 2-[6-chloro-5-(2-methoxy-phenoxy)-[2,2′] bipyrimidinyl-4-yloxy]-ethyl ester of formula V (100g, 1 eq) was added to the reaction mixture and the reaction mass was heated to 90¡ãC for 24-28 hours. Filtered the inorganic solid and washed the solid with dimethyl acetamide (100ml, 1vol). To the mixture of water (2.5L, 25vol) and concentrated hydrochloric acid (150ml, 1.5Vol) was added the filtrate at 0-5¡ãC. Maintained the stirring for 1-2 hours at 0-5¡ãC .Filtered the solid and washed with water (500ml, 5vol). Dissolved the wet cake in DCM (500ml, 5Vol) and added to a mixture of water (700ml,7vol) and concentrated hydrochloric acid (75ml, 0.75vol) at 10-15¡ãC.Stirred, separated the DCM layer and repeated the washing with mixture of water (700ml, 7vol) and concentrated hydrochloric acid (75ml, 0.75vol) at 10-15¡ãC. Separated the DCM layer and washed with water (500ml, 5vol). Distilled DCM under vacuum at 35-40¡ãC to get title compound (yield 110g, HPLC purity- 85percent).

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MATRIX LABORATORIES LTD; GORE, Vinayak; BINDU, Manojkumar; SHINDE, Dattatraya; KOKANE, Dattatrey; GHRAT, Sushant; DANDALA, Ramesh; WO2012/56468; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

915087-25-1, A common compound: 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, 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.

Synthesis of 4-(l-Cyano-cyclobutylamino)-2-fluoro-N-methyl-benzamide 6a.[00195] TMS-CN (29.7g, 300mmol) was added to a mixture of N-methyl-2-fluoro -4- aminobenzamide 4a (16.8g, lOOmmol) and cyclobutanone (14g, 200mmol) in 90%) acetic acid (200mL). The reaction mixture was stirred at 80C for 24h. The mixture was cooled and diluted with water (200mL). The suspension was extracted with ethyl acetate (3x200mL). Combined organic layers were washed with brine (4xl00mL), dried (MgS04) and concentrated in vacuo to dryness. The residue was triturated with a mixed solvent of hexanes and ethylether (20mL-20mL) to remove cyclobutanone cyanohydrin. The solid was collected by filtration, affording the title compound 6a (20g, 84% yield). MS(ES-API Negative): 246 (M-H)-. 1H NMR (CDC13, 500MHz): delta 7.92 (1H, dd, J=8.4, 8.4 Hz), 6.76 (1H, q, J=4.3Hz), 6.48 (1H, dd, J=8.3, 1.9Hz), 6.29 (1H, dd, J=14.3, 1.9Hz), 4.72 (1H, br s), 2.97 (3H, d, J=4.4Hz), 2.85-2.75 (2H, m), 2.4-2.35 (2H, m), 2.3-2.15 (1H, m), 1.95-1.85 (1H, m).

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-Amino-2-fluoro-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TONG, Youzhi; WO2011/29392; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, 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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below.

Step 1. A mixture of 4-fluorobenzenesulfonamide (1 equiv.), tert-butyl N-(azetidin- 3-yl)carbamate (1.3 equiv.), and diisopropylethylamine (1.3 equiv.) was stirred in acetonitrile at 150 C for 1 h in a sealed vial. The reaction mixture was then concentrated and purified by silica gel chromatography using MeOH (0 – 9%) in DCM.

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; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

366-49-4,Some common heterocyclic compound, 366-49-4, name is 2-Acetamido-4-fluorotoluene, molecular formula is C9H10FNO, 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.

Example 24; Preparation of Intermediate Compound 24G; Step A – Synthesis of Compound 24B; 24A 24B; A solution of 5-fluoro-2-methylaniline (24A, 25 g, 200 mmol) in toluene (250 mL) was treated with acetic anhydride (25 mL. 226 mmol) heated at reflux for 1 hour. The reaction mixture was cooled when a colorless solid precipitated out which was filtered and washed with a mixture of ether and hexanes. The colorless solid was taken in acetic acid (150 mL) and treated dropwise with a solution of bromine (9.6 mL, 186 mmol) in acetic acid (20 mL) and stirred at rt. for 12 hours. The solution was diluted with water and the solid separating out was filtered and washed to yield N-(4-bromo-5-fluoro-2-methylphenyl)acetamide (24B, 40 g) as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Acetamido-4-fluorotoluene, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2009/32124; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 138-38-5, name is 4-Ethylbenzenesulfonamide, molecular formula is C8H11NO2S, 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. 138-38-5.

In the same manner as in Example 1, 3-(2-chloro-4-phenylbenzyl)-5-[(4-ethylbenzene)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine (213 mg) was obtained as colorless crystals from 3-(2-chloro-4-phenylbenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (200 mg) and (4-ethylbenzene)sulfonamide (147 mg). 1H-NMR(CDCl3): 1.22(3H, t, J=8 Hz), 2.63-2.75(5H, m), 5.62(2H, s), 6.88(1H, d, J=8 Hz), 7.29(2H, d, J=8 Hz), 7.36-7.50(4H, m), 7.60(2H, d, J=8 Hz), 7.73(1H, d, J=2 Hz), 8.01(2H, d, J=8 Hz), 8.07(1H, d, J=8 Hz), 8.11(1H, d, J=8 Hz). Mass(ESI): m/z 529 (M-1) mp: 205-206 C.

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

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6348474; (2002); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

711007-44-2, A common compound: 711007-44-2, name is 2,3-Diaminobenzamide, 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.

General procedure: In a dark environment, a mixture of 2,3-diaminobenzamide(1.51 g, 10 mmol), PYTZ (20 mg), and ethanol (200 mL)was taken in an open pear-shaped bottle, stirred magneticallyat room temperature, and then aldehyde (10 mmol) wasadded slowly in 2 min. The bottle was exposed to visiblelight (Xenon, 10 A) under stirring condition. The reactionwas monitored by TLC. After the reaction completed, thereaction mixture was transferred to a three-neck bottle outsideof the photochemical reactor and air was introduced toensure that the intermediate was completely oxidized. Then,the solvent was evaporated in vacuum to 40 mL until thesolid appeared. The mixture was cooled down in an ice bathfor crystallization, filtration. The crude solid was recrystallizedfrom 25 mL ethanol (30 C) to get the target products.

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, 2,3-Diaminobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Li-Jie; Yang, Kang; Li, Chun-Yu; Sun, Ya-Quan; Chemical Papers; vol. 73; 11; (2019); p. 2697 – 2705;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

107017-73-2, Name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, 107017-73-2, 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.

Step 2: tert-Butyl[1-(bromomethyl)cyclopropyl]carbamateA solution of 92.5 g of carbon tetrabromide in 150 ml of ether is added at ambient temperature to a solution of 34.5 g of the compound of the above Step 1 and 73.5 g of triphenylphosphine in 750 ml of ether. After stirring for 20 hours, the reaction mixture is filtered and concentrated. Chromatography on silica gel (dichloromethane/cyclohexane: 50/50) allows 15 g of the expected product to be obtained.

Statistics shows that tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate is playing an increasingly important role. we look forward to future research findings about 107017-73-2.

Reference:
Patent; LES LABORATOIRES SERVIER; US2010/317698; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, I believe this compound will play a more active role in future production and life. 121492-06-6

EXAMPLE 365; 5-Bromo-3-[6-(2-methylamino-ethylamino)-2-propyl-2H-pyrazolo[3,4-d]pyrimidin-4-yl]-1,3-dihydro-indol-2-one hydrochloride; salt Example 188 (50 mg, 0.123 mmol) and N-(3-aminoethyl)-N-methyl carbamic acid t-butyl ester (214 mg, 1.23 mmol) were heated in 1 mL EtOH at 130 C. in microwave for 10 min. Upon cooling, the product precipitated in the reaction tube. The resulting solid was filtered and pumped dry before stirring in 5 mL of 4N HCl/dioxane for 1 h at r.t. The reaction mixture was pumped dry, triturated in ether and filtered to afford 38 mg (65%) of a yellow solid. mp 269-271 C.; MS (ES+calculated: 444.34; found: 444.63, 445.75 M+H). HPLC (95%) purity, retention time 3.937 minutes-Method C); 1H NMR (400 MHz, TFA) delta 8.73 (s, 1H), 7.89 (s, 1H), 7.54 (d, J=8 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 4.4 (m, 2H), 4.31 (br s, 2H), 4.07 (m, 1H), 3.85 (m, 3H), 3.10 (br s, 2H), 2.12 (m, 2H), 1.13 (t, J=7 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 121492-06-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cephalon, Inc.; US2007/281949; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, 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. 112101-81-2

EXAMPLE 32 (b) By following the same procedure as in Example 32 (a), (S)(+)-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide was obtained by using (S)(-)-N-acetyl-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide as the starting material. Melting point: 273-276 C. (decomposition). Elemental analysis for C10 H17 ClN2 O3 S: [alpha]D24: 6.0 (c=1.01, methanol). cl EXAMPLE 33 (a) In 120 ml of ethanol were dissolved 2.4 g of (R)(-)-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide and 1.2 g of 2-(o-ethoxyphenoxy)ethyl bromide, and the mixture was refluxed for 16 hours under heating. The solvent was distilled away, and after rendering alkaline the residue by the addition of 10% sodium hydroxide, and the oily material precipitated was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled away, and the residue was subjected to silica-gel column chromatography. The product was eluted with CHCl3 -methanol (9:5) to provide 1.5 g of the crude crystals of (R)(-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide, which was treated with HCl-ethanol to give a hydrochloric acid salt of (R)(-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide. Melting point: 228-230 C. Elemental analysis for C20 H29 ClN2 O5 S: [alpha]D-24: -4.0 (c=0.35, methanol).

Statistics shows that 112101-81-2 is playing an increasingly important role. we look forward to future research findings about R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4731478; (1988); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics