Month: August 2021

Reference of 1485-70-7, 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. 1485-70-7, name is N-Benzylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Amide 1a (48 mg, 0.25 mmol, 1 equiv), and Selectfluor (221 mg, 0.625 mmol, 2.5 equiv) were dissolved in 5 mL of acetonitrile at room temperature, and CuBr (42.6 mg, 0.3 mmol, 1.2 equiv) was added over a 40 min period in six portions. After all CuBr was added, the resulting mixture was stirred for extra 20 min, and then acetonitrile was evaporated under reduced pressure. Then, 20 mL of a saturated ammonium chloride solution was added into the reaction mixture and extracted by diethyl ether (25 mL × 4), the ether layers were combined and dried over Na2SO4, filtered, and evaporated under reduced pressure to give the crude product. Silica gel flash chromatography of the crude product (hexanes-ethyl acetate (10:1) to hexanes-ethyl acetate (4:1)) yielded pure imide 2a (45 mg, 0.22 mmol, 88% yield) together with unreacted 1a (3.2 mg, 0.017 mmol, 7%).

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

Reference:
Article; Jin, Zhuang; Xu, Bo; Hammond, Gerald B.; Tetrahedron Letters; vol. 52; 16; (2011); p. 1956 – 1959;,
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. 98-64-6, name is 4-Chlorobenzenesulfonamide, A new synthetic method of this compound is introduced below., Quality Control of 4-Chlorobenzenesulfonamide

General procedure: To a mixture of PS-tet-Cu(II) 2 (0.05 g) and arylboronicacid (0.7 mmol) in water (5 mL), K2CO3(1 mmol), sulfonamide(0.7 mmol) and water (5 mL) was added and the mixture was vig-orously stirred for the appropriate times under reflux conditions.After completion (as monitored by TLC), the catalyst was filteredand the reaction mixture was cooled to room temperature. Theresulting product was filtered and purified by recrystallizationusing ethyl acetate and n-hexane to afford N-arylated product. Allcompounds were compared with the corresponding compoundsprepared by the reported procedure [4,23?40]. All compounds wereknown and were characterized by spectral analysis or meltingpoints.1H NMR data of some compounds are given below.

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; Nasrollahzadeh, Mahmoud; Rostami-Vartooni, Akbar; Ehsani, Ali; Moghadam, Majid; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 123 – 129;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 354-38-1,Some common heterocyclic compound, 354-38-1, name is 2,2,2-Trifluoroacetamide, molecular formula is C2H2F3NO, 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.

g) Iodobenzene diacetate (18.98 g, 58.94 mmol) was added to (R)-4-(2-chloro-6-((R)-methylsulfinylmethyl)pyrimidin-4-yl)-3-methylmorpholine (17.08 g, 58.94 mmol), 2,2,2-trifluoroacetamide (13.33 g, 117.88 mmol), magnesium oxide (9.50 g, 235.76 mmol) and rhodium(II) acetate dimer (0.651 g, 1.47 mmol) in DCM (589 ml) under air. The resulting suspension was stirred at 20 C. for 24 hours. Further 2,2,2-trifluoroacetamide (13.33 g, 117.88 mmol), magnesium oxide (9.50 g, 235.76 mmol), iodobenzene diacetate (18.98 g, 58.94 mmol) and rhodium(II) acetate dimer (0.651 g, 1.47 mmol) were added and the suspension was stirred at 20 C. for 3 days. The reaction mixture was filtered and then silica gel (100 g) added to the filtrate and the solvent removed in vacuo. The resulting powder was purified by flash chromatography on silica, eluting with a gradient of 20 to 50% EtOAc in isohexane. Pure fractions were evaporated to afford N-[({2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidin-4-yl}methyl)(methyl)oxido-lambda6-(R)-sulfanylidene]-2,2,2-trifluoroacetamide (19.39 g, 82%); 1H NMR (400 MHz, DMSO-d6) 1.22 (3H, d), 3.17-3.27 (1H, m), 3.44 (1H, td), 3.59 (1H, dd), 3.62 (3H, s), 3.74 (1H, d), 3.95 (1H, dd), 4.04 (1H, br s), 4.28 (1H, s), 5.08 (2H, q), 6.96 (1H, s); m/z: (ESI+) MH+, 401.12 and 403.13.

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

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); A1;,
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 18469-37-9 as follows. COA of Formula: C9H10BrNO

General procedure: An 8.0 mL screw-cap vial containing a stirring bar was charged with [Ni(dMeObpy)(H 2 O) 2 (Br) 2 ] (8.5 mg, 0.018 mmol, 6 mol %), [[Ir{dF(CF 3 ) 2 ppy} 2 (bpy)]PF 6 ] (9.0 mg, 0.009 mmol, 3 mol %), amide (0.36 mmol, 1.2 equiv), aryl bromide (if solid) (0.3 mmol, 1.0 equiv) and Bu 4 N[OP(O)(OBu) 2 ] (338.8 mg, 0.75 mmol, 2.5 equiv). Next, the vial was closed, and three vacuum/argon cycles were carried out. Under inert atmosphere, a 2:1 mixture of dry t-BuOH/PhCF 3 was added (6.0 mL, 0.05 M) followed by addition of the aryl bromide (if liquid). After further sealing with Parafilm, the reaction was placed in the blue LED bay and stirred at rt until completion (a fan was added to disperse any heat coming from the blue LEDs). When completed, the reactions were taken to dryness and purified by column chromatography using an automated system (hexanes/EtOAc gradient), delivering the corresponding pure product.

According to the analysis of related databases, 18469-37-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zheng, Shuai; Gutierrez-Bonet, Alvaro; Molander, Gary A.; Chem; vol. 5; 2; (2019); p. 339 – 352;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, 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. Recommanded Product: tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

Intermediate 3 (400 mg, 1.6 mmol), tert-butyl [1-(hydroxymethyl)cyclopropyl]carbamate (390.5 mg, 2.01 mmol) andtriphenylphosphine (1683 mg, 6.4 mmol) were combined in THF (10 mL) and cooled to 0 C in an ice bath. DIAD (0.63 mL, 3.2 mmol) was added dropwise and the reaction mixture stirred for 10 mm before being allowed to warm to RT and stirred for a further 96h. The reaction mixture was concentrated under reduced pressure, and purified by Biotage Isolera chromatography (silica gel, eluting with heptaneEtOAc, 1:0 to 1:1). A second purification by Biotage Isolera chromatography (silicagel, eluting with heptane-EtOAc, 20:3) afforded 208.9 mg (23% yield) of the title compound as a colourless oil.LCMS (Analytical Method A) Rt = 1 .47 mm, MS (ESipos): m/z = 419 (M+H)+.

The synthetic route of 107017-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 122334-37-6,Some common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, 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.

To a -780C stirred solution of trimethyl (2-methylbut-3-yn-2-yloxy) silane (1 1.79 g, 75.15 mmol) in dry THF (100 mL), H-BuLi (14.08 mL, 22.54 mmol, 1.6 M in hexane) was added dropwise over 10 minutes under an inert atmosphere. After being stirred for 30 min at -78 0C, a solution of 4-chloro-N-methoxy-N-methylbenzamide (5.0 g, 25.0 mmol) in dry THF ( 10 mL) was added to reaction mixture and stirring was continued for an additional 1 h at -78 0C. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography eluting with 5-7 % EtOAc in hexanes to afford l-(4- chlorophenyl)-4-methyl-4-(trimethylsilyloxy) pent-2-yn-l-one (3.8 g, 57 %) as a light green oil.

The synthetic route of 122334-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2009/158393; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 158580-55-3,Some common heterocyclic compound, 158580-55-3, name is Methyl 2-chloro-4-(methylsulfonamido)benzoate, molecular formula is C9H10ClNO4S, 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 165 4-(N-(2-(lH-pyrrol-l-yl)ethyl)methylsulfonamido)-2-chloro-N-(4-chloro-3- (pyridin-2-yl)phenyl)b enzamide 200 muL of l-(2-bromoethyl)-lH-pyrrole and 556 mg of Cesium Carbonate were added to 150 mg of methyl 2-chloro-4-(methylsulfonamido)benzoate in DMF and stirred at room temperature for 16 hours. The reaction mixture was extracted in Ethyl Acetate twice with saturated bicarbonate and once with brine, dried over Magnesium Sulfate, filtered and concentrated to give methyl 4-(N-(2- (lH-pyrrol-l-yl)ethyl)methylsulfonamido)-2-chlorobenzoate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-chloro-4-(methylsulfonamido)benzoate, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CURIS, INC.; WO2009/126863; (2009); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 50667-69-1, A common heterocyclic compound, 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, molecular formula is C3H4F3NO2, 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.

Step i): A mixture of 2,6-dichlororbenzoic acid (4 g; 20,94 mmol), cone. H2S04 (50 mL) and N-(hydroxymethyl)trifluoroacetamide (2,996 g; 20,94 mmol) was stirred at rt overnight. The mixture was diluted with 500 mL crushed ice and 200 mL H20, the precipitate was filtered and dried to give crude 3-(trifluoromethylcarbonylamino-methyl)-2,6-dichloro-benzoic acid.

The synthetic route of 50667-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; PRIEPKE, Henning; DOODS, Henri; KUELZER, Raimund; PFAU, Roland; STENKAMP, Dirk; ROENN, Robert; PELCMAN, Benjamin; WO2011/48004; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 37073-15-7,Some common heterocyclic compound, 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, molecular formula is C7H7N3O2S, 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 alpha,beta-unsaturated aromatic or aliphatic acid (10 mmol), CH3SO2Bt (10 mmol) and Et3N (15 mmol) were refluxed in dry THF (50 mL) overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2 (100 mL). The organic phase was washed with brine (3 times) and dried over anhydrous Na2SO4. The organic phase was concentrated under vacuum to give a crude product, which could be further purified by recrystallization from a proper solvent.

The synthetic route of 37073-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xia, Ziming; Lv, Xin; Wang, Wencun; Wang, Xiaoxia; Tetrahedron Letters; vol. 52; 38; (2011); p. 4906 – 4910;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 63920-73-0,Some common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, 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 28. Preparation of 2-[4-(4-hydroxy-butoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one [0261] To a solution of 4-hydroxy-3,5-dimethyl benzaldehyde (5.00 g, 33.3 mmol) in DMF (30 ml_) were added 4-bromo butan-1-ol (6.11 g, 39.9 mmol) and CS2CO3 (16.24 g, 50.0 mmol). The reaction mixture was stirred at room temperature for 48 hours. Water was added and the products were extracted with ethyl acetate (2 * 200 ml_). The combined organic phase was washed with water (100 ml_), brine (100 ml_), and dried over anhydrous Na2SO4. Solvent was removed and the crude compound was purified using the Simpliflash system (40% ethyl acetate in hexane as eluent) to give 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde as a colorless liquid. Yield: 0.66 g (7%).[0262] To a solution of 2-amino-4,6-dimethoxy-benzamide (0.50 g, 2.53 mmol) and 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde (0.66 g, 2.53 mmol) in N,N-dimethyl acetamide (10 ml_), NaHSO3 (0.50 g, 2.79 mmol) and p-TSA (96 mg, 0.50 mmol) were added and the reaction mixture was heated at 115C for 16 hours, then cooled to room temperature. Solvent was removed under reduced pressure. Water (100 ml_) was added and the mixture was stirred for 1 hour. The solid separated was filtered and dried. The solid was again washed with diethyl ether to give the title compound as a white solid. Yield: 1.69 g (82%). 1H NMR (400 MHz, CDCI3): delta 9.10 (s, 1H), 7.66 (s, 2H), 6.83 (d, J = 2.4 Hz, 1 H), 6.46 (d, J = 2.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.85 (t, J = 6.0 Hz, 2H), 3.78 (m, 2H), 2.36 (s, 6H), 1.94 (m, 2H), 1.85 (m, 2H). MS (ES) m/z: 399.12 (M+1) (100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,6-dimethoxybenzamide, its application will become more common.

Reference:
Patent; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics