Category: amides-buliding-blocks

Related Products of 4793-24-2,Some common heterocyclic compound, 4793-24-2, name is 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, molecular formula is C7H5ClFNO4S, 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.

To a solution of 2-chloro-4-fluoro-5-sulfamoylbenzoic acid (3.2 g, 12.65 mmol) in THF (10 mL) was added 1M BH3 THF (38 mL, 38.0 mmol). After stirring 12h, the reaction mixture was quenched with MeOH and concentrated in vacuo. The residue was purified by chromatography (silica, EtO Ac-Hex) to afford 4-chloro-2-fluoro-5- (hydroxymethyl)benzenesulfonamide (1.9 g). To a suspension of 4-chloro-2-fluoro-5- (hydroxymethyl)benzenesulfonamide (1.78 g, 7.43 mmol) in DCM (10 mL) was added PBr3 (2.2 lg, 8.17 mmol). The reaction was stirred for 24 h when it was determined to be complete by GCMS. The reaction was carefully quenched with H20 and then partitioned between THF and brine. The organic layer was dried over Na2S04 and concentrated in vacuo to afford 5-(bromomethyl)-4-chloro-2-fluorobenzenesulfonamide (1.98 g) as an off-white solid. 1H-NMR (DMSO-d6, 400 MHz) delta 8.08 (d, J = 7.8 Hz, 1H), 7.84 (s, 2H), 7.80 (d, J = 9.9 Hz, 1H), 4.83 (s, 2H).

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-4-fluoro-5-sulfamoylbenzoic acid, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WO2011/71565; (2011); 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. 3984-14-3, name is N,N-Dimethylsulfamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-. 1,1?-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) ? ppm 1.28-1.49 (m, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below. 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). were added to a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, and the mixture was placed under N2. After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 C. for 2 h. After cooling to 30 C., N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered, and then concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 C., and heptane (2 L) was then added slowly. The resulting mixture was stirred and cooled to 0 C. It was then filtered. The filter cake was rinsed with a small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) ? 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/275930; (2007); 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. 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, A new synthetic method of this compound is introduced below., Formula: C10H15NO2S

Example 3Preparation of 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzene sulfonamide potassium salt using Acetone as a solvent and potassium hydroxide as a base; Acetone (45.0 ml), Potassium hydroxide (1.13 gm) and 4-tert-butylbenzenesulphonamide (1.65 gm) were added at 30 C. and stirred for 5 minutes. 4,6-dichloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidine (3.0 gm) was added at 30 C. and the temperature of the reaction mass was raised to reflux. The reaction mass was stirred at reflux for 6.5 hrs. The reaction mass was cooled gradually to room temperature. Acetone was distilled out from the reaction mass under vacuum below 40 C. Water (30.0 ml) was added to the reaction mass at room temperature and the resulting mass was stirred for 3.0 hrs. The precipitated solid was filtered, washed with water (2¡Á3.0 ml) and dried under vacuum at 55-60 C. for 6.0 hrs to obtain 4.04 gms of 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzene sulfonamide potassium salt. (% Yield: 89%)MS of solid: 564.1 (M+H), 548.1, 514.2, 434.1, 370.0, 352.1, 340.0, 324.1, 249.2, 237.1, 197.6, 182.9

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANDOZ AG; US2012/136015; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 6292-59-7, These common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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: To a solution of substituted acetophenone (72.4mmol) 10 in CH3CN (100mL), Br2 (11.57 g, 72.4 mmol) in CH3CN (20 mL) was addeddropwise. The reaction was stirred at room temperature overnight. Solvent wasconcentrated in vacuum and the residue was diluted with ethyl acetate (150 mL)and washed with brine. The organic layer was dried over anhydrous Na2SO4and evaporated. The resulting solid was triturated with cyclohexane (50 mL) andfiltrated to give alpha-bromoacetophenone 11as a white solid. The aqueous solution of NaN3 (4.71 g, 72 mmol) wasadded to the solution of 11 (60mmol) in CH3OH (80 mL) with stirring and cooling. After 4 h, 200 mLwater was added and a large amout of white precipitate was formed. Compound 12 was obtained by filtration. A mixture of 12 (26.3 mmol), hydrochloric acid (7.98 g, 78.8 mmol) and thecatalytic amount of Pd/C was stirred at room temperature under H2 (1atm) overnight. Solvent was separated from Pd/C by filtration through Celite.The solvent was removed and the resulting residue was triturated with ethylacetate (10 mL) and filtrated to give compound 13. A mixture of 14(29.1 mmol), EDCl (7.5 g, 39.67 mmol), HOBT (5.5 g, 39.67 mmol)and N-methylmorpholine (10.5 g, 105.80 mmol) in anhydrous CH2Cl2(50 mL) proceeded with stirring and cooling for 30 min. The reaction was addedby 13 and stirred at roomtemperature for 10 h. The white solid formed was filtrated to give part ofphenylacetamide 15. The filtrate was washed with waterand dried over anhydrous Na2SO4 and evaporated. Theresidue was chromatographed to give another part of 15. Et3N (10.55 g, 104.38 mmol) was added to asuspension of 15 (12.28 mmo) inacetic anhydride (15.65 g, 153.51 mmol) under nitrogen atmosphere at 0 ¡ãC. The mixture was stirred at 75 for 4 h and concentrated in vacuum. Water and CH2Cl2were added to the residue, and the organic layer was separated, washed withbrine, dried over anhydrous Na2SO4 andconcentrated. The resulting residue was triturated with diethyl ether (20 mL)and filtrated to give 16. To asuspension of 16 (21.87 mmol) inanhydrous CH3OH (120 mL), 28percent sodium methoxide in CH3OH(4.76 g, 22.97 mmol) was added slowly under nitrogen atmosphere at 0 ¡ãC. Thereaction was stirred at the same temperature for 1 h and acetic acid (1.48 g,22.97 mmol) was added slowly. The mixture was concentrated in vacuum and theresidue was diluted with CH2Cl2. The organic layer waswashed with water, dried over anhydrous Na2SO4 andconcentrated in vacuum. The resulting solid was triturated with diethyl ether(30 mL) and filtrated to give 17 as a pale yellow solid. NaH (0.13 g,3.25 mmol) was added to the solution of 17(1.28 mmol) in anhydrous DMF (5 mL) at 0 ¡ãC. The reaction was stirred at the sametemperature for 30 min, diluted with ethyl acetate (100 ml) and washed withwater (3 ¡Á 30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated todryness. 18 was obtained by a silicagel column chromatography as a yellow solid. A mixture of 18 (4.96 mmol), K2CO3 (0.69 g, 4.96 mmol),TBAB (0.16 g, 0.5 mmol) and 1,4-dibromobutane (4.28 g, 19.84 mmol) in CH3CN(20 mL) was stirred at 45 ¡ãC. The solvent was removed and the residue was diluted withethyl acetate (100 mL) and washed with water (3¡Á 30 mL). Theorganic layer was dried over anhydrous Na2SO4and concentrated. Intermediate 19was obtained by a silica gel column chromatography. To a solution of 19 (0.37 mmol) in CH3CN (5mL) were added KI (0.11 g, 0.75 mmol), K2CO3 (0.093 g,0.56 mmol) and substituted aromatic sulfonamide (0.56 mmol ). The reaction wasstirred in the refluxing CH3CN overnight. The solvent wasconcentrated and the residue was diluted with ethyl acetate (50 mL) and washed withbrine. The organic layer was dried over anhydrousNa2SO4 and concentrated in vacuum followed by a silicagel column chromatography to yield compounds 20a-m.

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Xinrui; Lu, Peng; Xue, Xiaojian; Qin, Hui; Fan, Chen; Wang, Yubin; Zhang, Qi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 849 – 853;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 20348-09-8 as follows. Safety of 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one

a) 3,4-Dihydro-2H-pyrido[3,2-&][l,4]oxazine; To an ice-cold solution of 4H-rhoyrido[3,2-][l,4]oxazin-3-one (5.00 g, 33.3 mmol) in TetaF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in TetaF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 00C and quenched the reaction with H2O (4 mL) followed by NaOH (4 mL, 15%) and H2O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85%) as a blue-gray powder: 1H NMR (500 MHz, OMSO-d6) delta 7.53 (dd, J= 4.5, 1.0 Hz, IH), 6.90-6.89 (m, IH), 6.61 (br s, IH), 6.44 (dd, J= 8.0, 3.0 Hz, IH), 4.08 (t, J= 4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e 31 (M + eta)

According to the analysis of related databases, 20348-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 147291-66-5, A common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, molecular formula is C12H18N2O2, 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.

The solution of EDCI (3.14g, 16.38mmol) and DMAP (100mg, 0.82mmol) in 10mL DCM was added dropwise to a mixture of tert-butyl-3-aminobenzyl-carbamate (2.0g, 9.01mmol) and benzoic acid (1.0g, 8.19mmol) in 20mL DCM at 0C under nitrogen atmosphere, and the mixture was warmed to r.t. and stirred overnight. After quenched with water and extracted with DCM, the organic layer was washed with 1M NaOH (20mL), 1M HCl (20mL), and saturated NaHCO3 (10mL), dried over Na2SO4, and concentrated under reduced pressure. The Boc-protected 12a was dissolved in DCM (5mL), trifluoroacetic acid (5mL) was added. The reaction mixture was allowed to stir for 2hat r.t. and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel and further purified by recrystallization (ethyl ether) to obtain the title compound as a white solid (1.2g, yield 64.8%). 1H NMR (600MHz, DMSO-d6) delta: 10.42 (1H, s), 8.34 (3H, s), 8.01-7.96 (3H, m), 7.70 (1H, d, J=8.4Hz), 7.61 (1H, t, J=8.4Hz), 7.54 (2H, t, J=7.8Hz), 7.41 (1H, t, J=7.8Hz), 7.22 (1H, d, J=7.8Hz), 4.04 (2H, s). 13C NMR (150MHz, DMSO-d6) delta: 166.1, 139.9, 135.2, 134.9, 132.1, 129.4, 128.8, 128.1, 124.4, 121.3, 121.0, 42.9.

The synthetic route of 147291-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Yaxue; Wang, Zhongli; Zhang, Jianchen; Zhou, Huchen; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 178 – 184;,
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. 147962-41-2, name is N-Propylsulfamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H10N2O2S

The compound of Example 1 (10 g; 20.6 mmol), propylsulfamide (3.1 g; 22.6 mmol; 1.1 eq.; prepared as described in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861), TBAF.3H20 (19.5 g; 61.7 mmol; 3 eq.) and potassium carbonate (8.5 g; 61.7 mmol; 3 eq.) were suspended in DMSO (100 mL). The mixture was heated to 100C for 1 h and then cooled to 20-25C. Water (100 mL) and DCM (100 mL) were added. The org. layer was washed 3 times with water (100 mL each time), 20% aq. citric acid (100 mL) and water (100 mL) before being concentrated under reduced pressure to dryness. The residue was suspended in EA (15 mL) and heated to reflux. Hept (30 mL) was added. The mixture was allowed to cool to 20-25C on its own. The precipitate was filtered off and rinsed with Hept (10 mL). The beige solid thus collected (11.0 g) was recrystallized from EA (30 mL) and Hept (25 mL) to afford the title compound as a white solid (6.4 g; 53% yield). (0323) The product had MS and NMR data equivalent to those reported in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861. LC-MS (method 1): tR = 1.89 min; 100% a/a.

According to the analysis of related databases, 147962-41-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; ABELE, Stefan; FUNEL, Jacques-Alexis; SCHINDELHOLZ, Ivan; WO2015/121397; (2015); 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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., COA of Formula: C7H7NO4S

Pathway ii: A mixture of 4-(aminosulfonyl)benzoic acid (4)(2 mmol) and N,N,N,N-tetramethyl-O-(1H-benzotriazol-1-yl)uraniumhexafluorophosphate (HBTU) (2 mmol) in DMF(2 mL) was stirred at room temperature for 1 h. Then, a solution of the appropriate amine derivative (2 mmol) in TEA (2 mmol) was added dropwise. The reaction mixture was left overnight and then quenched with water (10 mL) and extracted with EtOAc (3 5 mL).The organic phase was dried with Na2SO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography(DCM/MeOH 96:4), crystallized by treatment with a mixtureof Et2O and EtOH (1:1) to give the desired final compounds 5b, 5c,6a, 7a-f and 8a-d as white crystals. For compounds 5 a-d, 6a, 8a and 8d registered CAS numbers have been already assigned. However,their synthetic procedures, chemical properties and structural characterization are not available in literature.

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; Buemi, Maria Rosa; Di Fiore, Anna; De Luca, Laura; Angeli, Andrea; Mancuso, Francesca; Ferro, Stefania; Monti, Simona Maria; Buonanno, Martina; Russo, Emilio; De Sarro, Giovanbattista; De Simone, Giuseppina; Supuran, Claudiu T.; Gitto, Rosaria; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 443 – 452;,
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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Amino-4,6-dimethoxybenzamide

A mixture of N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide (0.770 g, 2.5 mmol), NaHSO3 (0.350 g, 3.3 mmol), and p-TsOH (0.100 g, 0.51 mmol) was added to a solution of 2-amino-4,6-dimethoxybenzamide (0.500 g, 2.5 mmol) in DMA (20 mL). The reaction was stirred at 130 C. for 5 hours and concentrated in vacuo. The residue was diluted with H2O and saturated NaHCO3, then extracted with CH2Cl2. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, afforded the title compound (0.670 g, 56%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6): delta 12.02 (s, 1H), 8.13 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 6.74 (d, J=1.9 Hz, 1H), 6.54 (d, J=2.0 Hz, 1H), 3.85-3.95 (m, 7H), 3.43-3.71 (m, 3H), 2.55-3.00 (m, 3H), 1.97-2.09 (m, 5H), 1.70-1.77 (m, 1H), 1.58-1.61 (m, 1H), 1.25-1.30 (m, 4H), 1.11-1.13 (m, 3H). ESI MS m/z 479 [M+H]+

The synthetic route of 63920-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 7341-96-0,Some common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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.

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 phenyl diazonium 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 shown as formula (g) is shown. The yield is 89%, dr value is equal to the 88:12. The product of the1As shown in Figure 13, H NMR schematic view thereof13C NMR schematic view as shown in Figure 14.

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

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