Category: amides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 4793-24-2, name is 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, 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 4793-24-2, COA of Formula: C7H5ClFNO4S

THF (3 ml_), 2-{4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}acetohydrazide (70 mg, 0.198 mmol), 5-(aminosulfonyl)-2-chloro-4-fluorobenzoic acid (50.1 mg, 0.198 mmol), HATU (75.2 mg, 0.198 mmol) and DIPEA (0.069 ml_, 0.395 mmol) were combined and the reaction mixture was stirred at rt for 45 min. Burgess Reagent (236 mg, 0.990 mmol) was added and the reaction was stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give 67 mg of the title compound. 1H NMR (CDCI3) delta 8.46 (d, 1 H), 7.47 (d, 1 H), 7.31-7.36 (m, 2 H), 7.23 (m, 1 H), 7.00-7.05 (m, 1 H), 6.94 (m, 1 H), 5.37 (s, 2 H), 4.39 (s, 2 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; SMITHKLINE BEECHAM CORPORATION; WO2008/157330; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1151665-15-4, 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 1151665-15-4 as follows.

To a solution of tert-butyl 2-chloro-7 ,8-dihydro-5H- 1 ,6-naphthyridine-6-carboxylate (1.0 g,3.7 mmol) in toluene (10 mL) was added KOH (0.6 g, 11.1 mmol) at 0 C and the mixture was stirred for 0.5 hr. To the resulting mixture was added a solution of BnOH (0.34 g, 5.6 mmol) in toluene (10 mL) followed by 18-crown-6 (100 mg) at 0C. The resulting mixture was heated with stirring at 130 C for 2 hrs and then filtered. The filtrate was concentrated in vacuo. Theresidue was purified by flash column to give tert-butyl 2-benzyloxy-7,8-dihydro-5H-1,6- naphthyridine-6-carboxylate (1 g).

According to the analysis of related databases, 1151665-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); 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. 4664-01-1, name is 3,4-Pyridinedicarboximide, A new synthetic method of this compound is introduced below., SDS of cas: 4664-01-1

Step 1 To 10% aqueous sodium hydroxide solution (100 mL) was added bromine (1.93 mL, 38.6 mmol) under ice-cooling, and 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione (5.20 g, 35.1 mmol) was subsequently added. 10%-Aqueous sodium hydroxide solution (60 mL) was added to the reaction mixture, and the mixture was stirred with heating at 90 C. for 40 min. After allowing to cool to room temperature, 50% sulfuric acid was added to adjust the reaction mixture to pH 3. The precipitated insoluble material was collected by filtration, and the solid was washed with water to give 3-aminoisonicotinic acid as a pale-yellow powder (5.00 g, 100%). 1H-NMR (200 MHz, DMSO-d6) delta: 7.46 (1H, d, J=5.1 Hz), 7.73 (1H, d, J=5.1 Hz), 8.21 (1H, s).

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; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 17641-08-6,Some common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, 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: A mixture of 4-(5-mercapto-1,3,4-oxadiazol-2-yl)benzenesulfonamide (9) (1mmol), various substituted 2-chloro-N-phenylacetamide 11a-j (1mmol) and K2CO3 (1.5mmol) was refluxed in acetone (15ml) for 3-4h. The reaction was monitored with TLC and after completion of the reaction, excess of solvent was evaporated and diluted with water (about 100ml). The precipitated was separated out, filtered washed with water and recrystallized with an appropriate solvent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-N-(3-methoxyphenyl)acetamide, its application will become more common.

Reference:
Article; Angeli, Andrea; Kumar, Rajiv; Sharma, Pawan K.; Sharma, Vikas; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 193; (2020);,
Amide – Wikipedia,
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Some common heterocyclic compound, 22117-85-7, name is 2-Methoxy-5-sulfamoylbenzoic acid, molecular formula is C8H9NO5S, 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. Safety of 2-Methoxy-5-sulfamoylbenzoic acid

(2) N-(3,5-Bis(trifluoromethyl)phenyl]-2-methoxy-5-sufamoylbenzamide. Using 2-methoxy-5-sulfamoylbenzoic acid and 3,5-bis(trifluoromethyl)aniline as the raw materials, the same operation as the example 24 gave the title compound. Yield: 24.2%. 1H-NMR(DMSO-d6): delta 3.97(3H, s), 7.38(2H, s), 7.39(1H, d, J=8.7Hz), 7.85(1H, s), 7.96(1H, dd, J=8.7, 2.4Hz), 8.06(1H, d, J=2.4Hz), 8.43(2H, s), 10.87(1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22117-85-7, its application will become more common.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1352650; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 60144-53-8,Some common heterocyclic compound, 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate, molecular formula is C11H14FNO2, 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.

Part II: Preparation of (4-fluorophenyl)-(4-iodo-benzyl)-carbamic acid terf-butyl esterA solution of (4-fluorophenyl)-carbamic acid terf-butyl ester (9.98 g, 47.3 mmol) in anhydrous tetrahydrofuran (150 mL) was cooled to 0C and treated with sodium hydride (60% dispersion in mineral oil, 2.3 g, 56.8 mmol). The mixture was warmed to room temperature and stirred for 30 minutes. To the reaction was added 1- bromomethyl-4-iodo-benzene (14.0 g, 47.3 mmol) and the mixture was allowed to stir at room temperature overnight. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, washed with brine (50 ml_), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography (silica gel; 5% ethyl acetate in hexanes) provided (4-fluorophenyl)-(4-iodo-benzyl)-carbamic acid terf-butyl ester (18 g, 42.1 mmol) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (4-fluorophenyl)carbamate, its application will become more common.

Reference:
Patent; WYETH; WO2008/73936; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 317595-54-3, 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. 317595-54-3, name is tert-Butyl (2-aminocyclohexyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 0.3 g (3 mmol) of ethyl glyoxylate was dissolved in 30 mL of anhydrous dichloromethane containing molecular sieves (4A). Then, 0.7 g (3 mmol) of N-[(1R,2R)-2-aminocyclohexyl)benzenesulfonamide (1a) was added and the solution was stirred for 24 h at room temperature. The reaction mixture was then transferred to the three-necked flask equipped with a mechanical stirrer and the source of argon and was cooled to -78 C. 0.25 mL (3 mmol) of trifluoroacetic acid, 0.25 mL(2 mmol) of BF3¡¤Et2O, and 0.35 mL (4 mmol) of freshly distilled cyclopentadiene were then added in 10 min intervals. After 24 h of stirring at -78 C, the reaction was quenched by additionof saturated aqueous NaHCO3 The reaction mixture was filtered through a bed of cellite, and extracted with CH2Cl2 (3¡Á20 mL). The combined organic phases were dried over Na2SO4, filtered, and solvent was evaporated. 2.75 g of solid residue was dissolved in EtOH and 0.15 g of palladium on carbon (10%w/w) and 0.6 g of K2CO3 were added. The suspension was stirred under 1 atm of hydrogen for 24 h. The reaction mixture was filtered through a cellite, and ethanol was evaporated. Than mixture was dissolved in dichloroethane (20 mL), washed with water (3 ¡Á 20 mL) and evaporated. After column chromatography(eluent CHCl3) compound 3a product was obtained as colorless oil. Compounds 3b-c were synthesized analogously using N-((1R,2R)-2-aminocyclohexyl)-4-methylbenzenesulfonamide(1b), and tert-butyl-(2-aminocyclohexyl)carbamate (1c),respectively. In case of 1c substrate, trifluoroacetic acid was not added. When N-((1R,2R)-2-aminocyclohexyl)benzamide(1d) and N-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea (1e) were used, the last step (double bond hydrogenation) was ineffective and 2-azabicyclo[2.2.1]hept-5-ene derivatives 2d, 2e were obtained.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (2-aminocyclohexyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Dorsz, Mateusz; Kleniewska, Karolina; Wojaczy?ska, Elzbieta; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 2; (2016); p. 279 – 282;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 478832-21-2, name is tert-Butyl 4-hydroxyazepane-1-carboxylate, molecular formula is C11H21NO3, 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. Application In Synthesis of tert-Butyl 4-hydroxyazepane-1-carboxylate

To a solution of tert-butyl 4-hydroxyazepane-i-carboxylate (3.0 g, 14.0 mmol, 1.0 equiv.) and N,N-diisopropylethylamine (3.2 mL, 18.0 mmol, 1.3 equiv.) in (1574) dichloromethane (70 mL) was added methanesulfonyl chloride (1.2 mL, 15.0 mmol, 1.1 equiv.). The reaction mixture was stirred at room temperature for 1 hour and then water was added. The organic layer was separated and then washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound (3.87 g, 95 %). (1575) NMR (CDC13) delta 4-97 – 4-76 (m, 1 H), 3.62 – 3.24 (m, 4 H), 3.00 (s, 3 H), 2.14 – 1.83 (m, 4 H), 1.68 (q, 2 H), 1.45 (s, 9 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 478832-21-2, its application will become more common.

Reference:
Patent; INFLAZOME LIMITED; COOPER, Matthew; MILLER, David; MACLEOD, Angus; VAN WILTENBURG, Jimmy; THOM, Stephen; ST-GALLAY, Stephen; SHANNON, Jonathan; (352 pag.)WO2019/8025; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 227940-71-8, name is tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

To a solution of 3 (350 mg, 1.11 mmol) in 30mL of dry ethanol was added 28 % of the Pd, 10 wt. % on activated carbon, and H2 was bubbled through the reaction mixture for 4 hrs. The reaction was monitored by TLC. The solution was filtered through a sintered funnel and evaporated to yield 230 mg of the product 4. Yield: 92 %. (HRMS): calcd for C12H23N2O2 m/z 227.1760, found m/z 227.1750

The synthetic route of 227940-71-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Haridas; Sadanandan, Sandhya; Sharma, Yogesh K.; Chinthalapalli, Srinivas; Shandilya, Ashutosh; Tetrahedron Letters; vol. 53; 6; (2012); p. 623 – 626;,
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. 459817-82-4, name is tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H13NO5S

Methyl 4-chloro-lH-pyrrolo[2,3-b]pyridine-2-carboxylate (2 g, 9.50 mmol) was taken up in DMF (30 ml), cooled to 0 C and KOtBu (1.1 g, 9.80 mmol) was added. After 30 min tert-butyl 2,2-dioxooxathiazobdine-3-carboxylate (2.3 g, 10.3 mmol) was added, the cooling bath removed, and the mixture stirred at rt for 1.5 h. Aq. 10% citric acid (50 ml) and EtOAc (30 ml) were added and the organic layer separated. The aqueous layer was extracted with EtOAc (3 x 15 ml) and the combined organics were washed with water (3 x 20 ml), brine (20 ml), dried over Na^SOr. filtered and concentrated to give the product as a gum, which solidified upon standing (2.9 g, 86%). MS ES+ m/z 354 [M+H]+.

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; PETRA PHARMA CORPORATION; KESICKI, Edward A.; RAVI, Kannan Karukurichi; LINDSTROeM, Johan; PERSSON, Lars Boukharta; LIVENDAHL, Madeleine; VIKLUND, Jenny; GINMAN, Tobias; FORSBLOM, Rickard; RAHM, Fredrik; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (478 pag.)WO2019/126733; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics