Amides-buliding-blocks

Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, 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. Formula: C8H6FNO2

To a stirred solution of step 2 intermediate (2.7 g, 16.157 mmol) in sulphuric acid (3 ml) a mixture of nitric acid (69 %, 0.72 ml, 16.157 mmol) and concentrated sulphuric acid (2 ml) was drop wise added at 0 C under nitrogen atmosphere. The reaction mixture was stirred at 0 C for 30 min. The reaction mixture was quenched with ice-cooled water and solid was precipitated. The precipitated solid was dissolved in ethyl acetate (30 ml) and washed with aqueous saturated solution of sodium bicarbonate (150 ml). The ethyl acetate layer was dried and filtered and dried (Na2S04) and concentrated to yield 2.6 g of product as yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 4.79 (s, 2H), 7.26 (d, J = 12.0 Hz, 1H), 7.63 (d, / = 7.2 Hz, 1H), 1 1.03 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103361-99-5, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin Sundarlal; KUMAR, Sukeerthi; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; WO2013/153539; (2013); A1;,
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Reference of 201162-53-0, These common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, 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.

A solution of tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate (1 g, 4.71 mmol, 1.00 equiv), potassium carbonate (1.3 g, 9.41 mmol, 2.00 equiv), 5-chloropyridin-2-carbonitrile (651 mg, 4.67 mmol, 1.00 equiv) in DMF (10 mL) was stirred for 2 h at 80 C. in an oil bath. The solids were filtered out. The resulting solution was extracted with 3*20 mL of ether and the organic layers combined. After concentration, the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (1:2) to afford 1 g (68%) of the title compound as a solid. LCMS (ESI, m/z): 315.17 [M+H]+

Statistics shows that 3-Boc-3,8-Diazabicyclo[3.2.1]octane is playing an increasingly important role. we look forward to future research findings about 201162-53-0.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
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Electric Literature of 1888-91-1, A common heterocyclic compound, 1888-91-1, name is N-Acetylcaprolactam, molecular formula is C8H13NO2, 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: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde(7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.

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; Antoniak, Damian; Sakowicz, Arkadiusz; Loska, Rafal; Makosza, Mieczyslaw; Synlett; vol. 25; 9; (2014);,
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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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6FNO2S

General procedure: A dry round bottom flask was cooled to rt under nitrogen, and was charged with Pd2(dba)3 (3.38mg, 0.0037mmol), cesium carbonate (361mg, 1.11mmol), and arenesulfonamide (69mg, 0.44mmol). Tertiary-butanol (2mL) was added, followed by ligand, xantphos (6.4mg, 0.011mmol) and 9-chloroacridine (80mg, 0.37mmol). The resulting suspension was stirred at rt for 5min, then heated to 80C for 12-17h. The reaction mixture was then cooled to rt and filtered through suction filtration. The organic fraction was evaporated, and the resulting residue was purified by silica gel chromatography with a hexane/Et-OAc as eluent (60:40).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chourasiya, Sumit S.; Wani, Aabid A.; Nagaraja; Chakraborti, Asit K.; Bharatam, Prasad V.; Tetrahedron; vol. 74; 27; (2018); p. 3634 – 3641;,
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Synthetic Route of 37073-15-7, The chemical industry reduces the impact on the environment during synthesis 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, I believe this compound will play a more active role in future production and life.

A flame-dried, two necked, round bottomed flask was charged with methanesulfonyl benzotriazole (34b) (1.0 g, 0.005 mol), 2-furoic acid (0.57 g, 0.005 mol), dry triethylamine (2 ml_), and dry THF (20 ml_) under argon. The resulting solution was heated at reflux for 18 hours. After this time, the THF was removed under reduced pressure to afford a cream coloured residue, which was taken up in ethyl acetate and washed with 1 M HCI (3 chi 30 ml_). The ethyl acetate was dried (MgS04) and removed in vacuo to afford a white solid which was recrystallised from toluene to give the title compound (34c) as fluffy white crystals (0.82 g, 77.0 %); mp 171 – 172 C; Rf = 0.48 (DCM : petroleum ether, 5 : 5); Analysis Calcd. for Cn H7N302: C, 61.97; H, 3.31 ; N, 19.71 %. Found C, 61.73; H, 3.31 ; N, 19.71 %; vmax (KBr) / cm”1 3142 (NH), 1681 (C=0), 1556, 1447; deltaEta (d6-DMSO, 300 MHz) 8.30 (3H, m, H5, H8, H5), 8.08 (1 H, dd, 3. 4.= 3.8, Jy, v= 0.6, H3), 7.82 (1 H, td, J6, 5/ 7= 7.2, 6, 8= 1.2, H6), 7.65 (1 H, td, J7, 6/s=7.2, J7, 5= 1.2, H7), 6.94 (1 H, dd, 4. 3.= 3.8, 4. 5.= 1.8, H4); 5c(d6-DMSO, 75 MHz) 155.0 (CO), 150.8 (C5), 145.5 (C9), 144.4 (C2) 132.1 (C4), 131.3 (C6), 127.1 (C7), 125.4 (C3), 120.6 (C5 or C8), 114.7 (C5 or C8), 113.9 (C4).

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, 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF SUNDERLAND; TODD, Adam; ANDERSON, Rosaleen Joy; SMALL, David Antony Philip; GROUNDWATER, Paul William; BENTON, Matthew Richard; WO2014/96864; (2014); A1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, 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 19047-31-5, Computed Properties of C5H8ClNO

General procedure: To a solution of 5- bromine -2- chlorophenol (2.9g, 14.3mmol) in 50mL acetonitrile was added K2CO3 (2.5g,17.1mmol), and stirred for 30min intermediate product 10 was added and the solution was heated to 80C for 4h. The reaction solution was concentrated, water (100mL) was added, and extracted with EtOAc. The organic layer was collected and washed with water and brine for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford intermediate product 11.

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-Chloro-N-cyclopropylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yan, Guoyi; Pu, Chunlan; Lan, Suke; Zhong, Xinxin; Zhou, Meng; Hou, Xueyan; Yang, Jie; Shan, Huifang; Zhao, Lifeng; Li, Rui; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 667 – 686;,
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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,
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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

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,
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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);,
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Amide – an overview | ScienceDirect Topics