Amides-buliding-blocks

Reference of 518057-72-2, These common heterocyclic compound, 518057-72-2, name is 5-Amino-2-fluorobenzamide, 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.

To 5-amino-2-fluoro-benzamide (70.54 mg, 0.4576 mmol) and diisopropylethylamine (178 mg, 1.37 mmol) in dichloromethane (2.4 mL) cooled at 0C was added dropwise a solution of 6-[2- chloro-4-(trifluoromethoxy)phenoxy]-2-fluoro-3-(trifluoromethyl)benzoyl chloride (200 mg, 0.46 mmol) in dichloromethane (2.4 mL). The reaction was stirred at room temperature overnight. The crude material was purified by silica gel chromatography (ethyl acetate/hexane gradient) to obtain N-(3- carbamoyl-4-fluoro-phenyl)-6- [2-chloro-4-(trifluoromethoxy)phenoxy] -2-fluoro-3 – (trifluoromethyl)benzamide (85 mg, 33%). ESI-MS m/z calc. 554.03, found 555.0 (M+l)+; retention time (Method B): 1.9 minutes (3 minute run). NMR (400 MHz, DMSO-d6) delta 11.06 (s, 1H), 7.98 (dd, J = 6.4, 2.8 Hz, 1H), 7.95 – 7.82 (m, 2H), 7.80 – 7.59 (m, 3H), 7.52 (d, J = 2.4 Hz, 2H), 7.30 (dd, J = 10.0, 9.1 Hz, 1H), 6.85 (d, J = 8.8 Hz, 1H) ppm.

Statistics shows that 5-Amino-2-fluorobenzamide is playing an increasingly important role. we look forward to future research findings about 518057-72-2.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
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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. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrNO2S

To a stirring solution of 5-(3-(difluoromethoxy)-2-hydroxy-4- methoxyphenyl)isobenzofuran-l(3H)-one (80 mg, 0.246 mmol) in acetonitrile (10 mL) was added potassium carbonate (102 mg, 0.738 mmol) and 4- (bromomethyl)benzenesulfonamide (124 mg, 0.496 mmol) and the resultant reaction mixture was heated to 70 ¡ãC for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, 0-70percent ethyl acetate in pet ether) to afford the title compound as a solid (40 mg, 33percent).UPLC-MS (M + l) : 492.08 ; UPLC-MS RT (min) : 2.3

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; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; HORNEMAN, Anne Marie; LAU, Jesper Faergemann; LARSEN, Jens Christian H¡ãjland; WO2011/134468; (2011); A1;,
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Related Products of 885-70-1, 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. 885-70-1, name is 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 1 11-Acryloyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and a mixture thereof with the corresponding 11-(3-chloro-propionyl) compound STR35 Solutions of 3-chloropropionyl chloride (6.3 g) in dioxane (60 ml) and triethylamine (8.4 g) in dioxane (60 ml) were added simultaneously to a refluxing suspension of 5,11-dihydro-6H-pyrido [2,3-b][1,4]benzodiazepin-6-one (9.45 g – see DT-PS 1179943) in dioxane (300 ml) and the mixture was heated under reflux for 6 hours and evaporated to give a mixture of the two title compounds in which the acryloyl compound predominated. Crude mixtures of the 11-acryloyl and 11-(3-chloropropionyl) compounds prepared using this procedure were used in Examples 22-30. The residue was purified by chromatography on silica using dichloromethane plus 0-2% methanol as eluant. Appropriate fractions were combined and evaporated to give the title 11-acryloyl compound as a colourless solid, 3.2 g, (27%) which was used directly in Examples 11-21.

The synthetic route of 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alker; David; Cross; Peter E.; US5418229; (1995); A;,
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Electric Literature of 224789-21-3, 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 224789-21-3 as follows.

Example 8 Preparation of 2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-t hione 2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-one (50g (0.16mol)), phosphorus pentasulfide (17.8g (0.08mol)), pyridine (250ml)were added into a 500ml three-neck flask with a mechanical stirrer, stirred, heated and refluxed for 6 hours, TLC tracing was performed until the reactants were totally disappeared. The solvent pyridine was removed by distilling under reduced pressure, concentrated ammonia water ((25-28%) 75ml)and ethanol (300ml)were added, heated and refluxed for 30 min. It was cooled, filtered, dried, and crude product (45g)was obtained. The crude product was heated and solved into chloroform (150ml), activated carbon (5g)was added, stirring and reflux was performed for 30 min, it was filtered and the filtrate was washed with saturated brine and water consequently and dried with magnesium sulfate anhydrous, chloroform was removed by distilling, the obtained solid was re-crystallized with ethanol and dried, solid (38g)was obtained with a yield of 72%.

According to the analysis of related databases, 224789-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; WANG, Jianping; WANG, Jianguo; EP2666776; (2013); A1;,
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These common heterocyclic compound, 116332-54-8, name is 4-Fluoro-N-methoxy-N-methylbenzamide, 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. COA of Formula: C9H10FNO2

PREPARATIVE EXAMPLE 2 4-Fluoro-2-(2-pyridyl)acetophenone (2) To a solution of lithium diisopropylamide (Aldrich Chemical Co. 2.0M in heptane,THF ethylbenzene) 5.2 mL (10.5 mmol) in 6 mL of anhydrous THF at -78 C. under nitrogen was added 0.93 g (10 mmol) of 2-picoline dropwise. The reaction mixture was stirred for 20 minutes and then treated with a solution of 1.71 g (5.3 mmol) of 4-fluoro-(N-methyl-N-methoxy)-benzamide in THF. The reaction mixture was warmed to 0 C. and quenched by addition of 10 mL of brine. The mixture was extracted with ethyl acetate (3*10 mL) and the combined organic phases were dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo to give a solid. H1 NMR (CDCl3 300 MHz): 4.49 (s); 6.0 (s); 6.97 (m); 7.-3-7.12 (m); 7.62 (m); 7.82 (m); 8.10 (dd); 8.28 (bd); 8.57 (bd). The compound exists in a keto/enol equilibrium as determined by H1 -NMR. FAB ms:216 (M+ +1).

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

Reference:
Patent; Merck & Co., Inc.; US5837719; (1998); A;,
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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. 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H21NO3

To a suspension of 60% sodium hydride dispersion (0.270 g, 6.75 mmol) in 20 mL DMSO, (lR,3r,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (1.0 g, 4.399 mmol) was added. After stirring at room temperature for 20 min, l-(benzyloxy)-4-fluorobenzene (0.89 g, 4.401 mmol) was added and mixture was stirred at 90C (oil bath). After 2.5 d, dark mixture was extracted with water and AcOEt (3x). Combined organic phases were dried over MgS04, filtered, and concentrated. Residue (ca. 3 g) was dissolved in 40 mL CH2C12 and triethylamine (1 mL, 7.175 mmol) and di-teri-butyl dicarbonate (0.961 g, 4.401 mmol) were added. After 10 min, mixture was transferred into a separatory funnel and extracted with water and CH2C12. Organic phases was dried over MgSO/t, filtered, and concentrated. Residue was purified by Biotage column chromatography (Si02, hexane/ AcOEt gradient) to give (lR,3r,55)-teri-butyl 3-(4-(benzyloxy)phenoxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (0.34 g, 0.830 mmol, 18.9%) as a white solid. Exact mass calculated for C25H31F6N04: 409.23, found: LCMS m/z = 410.2 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.47 (s, 9H), 1.93-1.97 (m, 4H), 2.07-2.17 (m, 4H), 4.49-4.53 (m, 2H), 4.50-4.52 (m, 1H), 5.01 (s, 2H), 6.75-6.77 (m, 2H), 6.89-6.91 (m, 2H), 7.31-7.43 (m, 5H).

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; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
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Electric Literature of 7150-72-3,Some common heterocyclic compound, 7150-72-3, name is tert-Butyl vinylcarbamate, molecular formula is C7H13NO2, 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 10 mL round-bottomed flask equipped with a rubber septum and a magnetic stir bar was charged with 1 (1.0 equiv), 2 (2.5 equiv), 3 (2.0 equiv), and fac-Ir(ppy)3 (0.01 equiv). The flask was evacuated and backfilled 3 times with N2. DMSO was then added with syringe under N2. The mixture was then irradiated by white LED strips. After completion of the reaction (6 h, as judged by TLC analysis), the mixture was poured into a separatory funnel containing sat. aq NaHCO3 (20mL) and EtOAc (20 mL). After extraction with EtOAc, the organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure after filtration. The crude product was purified by flash chromatography on silica gel to afford the desired product 4.

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 vinylcarbamate, its application will become more common.

Reference:
Article; An, Xiao-De; Yu, Shouyun; Synthesis; vol. 50; 17; (2018); p. 3387 – 3394;,
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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. 354-38-1, name is 2,2,2-Trifluoroacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2,2,2-Trifluoroacetamide

General procedure: To a solution of trifluoroacetamide (2.00 g,18 mmol), NaI (7.95 g, 53 mmol) and styrene (2.05 mL, 18 mmol) in CH3CN (80 mL) t-BuOCl (6.10 mL, 53 mmol) was added dropwise in argon atmosphere in the dark and cooling to 10 C . The mixture was stirred for one day, the solvent removed under reduced pressure, the residue dissolved in diethyl ether (80 mL), washed with aqueous Na2S2O3 and dried over CaCl2. The solvent was removed in vacuum. Purification of the residue (5.57 g) by separation from resinification products on silica column with successive elution with hexane, ether-hexane (1:1) and ether recovered trifluoroacetamide (0.4 g) and gave the title compound (9) (4.80 g, 79%), which was crystallized from methylene chloride. Colorless crystals, mp 109 C . gammamax (KBr) 3324, 3088, 3035, 2972,2951, 2913, 1699, 1553, 1496, 1455, 1365, 1216, 1182, 1076, 999, 885,804, 762, 729, 702, 655, 599, 573, 498 cm-1; deltaH (CDCl3), ppm: 7.45-7.35 (2H,m,CH), 7.33-7.26 (3H, m, CH), 7.00 (1H,d, J 5.5 Hz,NH), 5.14 (1H, ddd, J 7.1, 5.9, 5.5 Hz,CH), 3.58 (1H, dd, J 10.7, 5.9 Hz, CHB), 3.54 (1H, dd, J 10.7, 7.1 Hz, CHA); deltaC (CDCl3), ppm: 157.0 (q, J 37.6 Hz,C=O), 138.1 (Ci), 129.5 (Cm), 129.2 (Cp), 126.5 (Co), 116.0 (CF3, J 288.5 Hz), 54.9 (CHNH) 8.7 (ICH2).19F NMR, deltaF, ppm: 75.36. Anal. Calcd: C, 35.01; H, 2.64; N, 4.08; I 36.99; F 16.61. C10H9F3INO.Found: C, 35.02; H, 2.53; N, 3.98; I 37.10; F 16.56.

The synthetic route of 354-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shainyan, Bagrat A.; Moskalik, Mikhail Yu.; Astakhova, Vera V.; Sterkhova, Irina V.; Ushakov, Igor A.; Tetrahedron; vol. 71; 45; (2015); p. 8669 – 8675;,
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Reference of 121492-06-6, These common heterocyclic compound, 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, 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.

Example 95; l,l-dimethylethyl (2-{r8-(2.6-difluorophenvn-4-f5-frf4- fluorophenyl)aminolcarbonyl}-2-methylphenv?-7-oxo-7,8-dihvdropyrido[2.3-^rhoyrimidin-2-yl]amino|ethyl)methylcarbarnateTo a solution of 3-[8-(2,6-difluorophenyl)-2-(methylsulfmyl)-7-oxo-7,8- dihydropyrido[2,3-d]pyrimidin-4-yl]-N-(4-fluorophenyl)-4-methylbenzamide (50 mg, 0.09 mmol) in DCM (5 niL) was added 1,1-dimethylethyl (2-aminoethyl)- methylcarbamate (0.09 mL, 0.5 mmol). The resultant mixture was stirred at room temperature overnight. The mixture was concentrated under vacuo. Flash chromatography (90% CH2Cl2 / 7% MeOH / 3% NH4OH) then provide the title compound (61 mg, 100%). LC-MS (ES) m/z 659 (M+H)+; 1H-NMR(CDCl3) delta 1.39 (s, 9H), 1.70 (br, IH), 2.32 (s, 3H), 2.65 (s, 2H), 2.82 (s, 2H), 3.22 (s, 3H), 3.60 (br, IH), 6.34 (d, IH)5 7.03 (m, 4H)5 7.34 (m, IH), 7.48 (m. 2H), 7.64 (m, IH), 7.84 (m, 2H)5 8.14 (d, IH).

Statistics shows that N-Boc-(2-Aminoethyl)-N-methylamine is playing an increasingly important role. we look forward to future research findings about 121492-06-6.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/104915; (2006); A2;,
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Related Products of 17641-08-6, A common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, 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: A mixture of 12-benzyl-6-thioxo-6,7,11b,12-tetrahydro-13H-quinazolino[3,4-a]quinazolin-13-one 8 (1 mmol), 2-chloro-N-substituted acetamide 9 (1 mmol), and potassium iodide (1 mmol) in acetone (8 mL) was heated at room temperature for 5-48 h. After completion of the reaction, water (8 mL) was added to the reaction mixture, and the precipitates were filtered off and recrystallized from EtOH/H2O (90/10) to give the corresponding product 10.

The synthetic route of 17641-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohammadhosseini, Negar; Saeedi, Mina; Moradi, Shahram; Mahdavi, Mohammad; Firuzi, Omidreza; Foroumadi, Alireza; Shafiee, Abbas; Turkish Journal of Chemistry; vol. 41; 1; (2017); p. 125 – 134;,
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