Amides-buliding-blocks

Synthetic Route of 103361-99-5,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.

To a solution of 2H-1 ,4-benzothiazin-3(4H)-one (intermediate 33, 3.1 g, 18.55 mmol) in dry Toluene (15 mL) in a glass tube was added Lawesson’s reagent (4.50 g, 1 1 .13 mmol, 0.6 eqv) and the mixture reacted in a microwave reactor at 100 C for 5 minutes). Cyclohexane was added, and the resulting solid was filtered. The solid was dissolved in Et^O and the solvent removed not quite to dryness. This concentrated mixture was purified using a Biotage SP1 purification system using Normal phase Silica SNAP 4×50 g (because of low solubility) column in the gradient of ethyl acetate in cyclohexane (8 % in 1 CV, 8-30 % in 10 CV, 30-66 % in 10 CV) to give the title compound (2 g); m/z (ES): 184.10 [M+H]+; 1H NMR (600 MHz, DMSO-d6) delta ppm 4.86 (s, 2 H) 6.84 – 6.88 (m, 1 H) 6.92 – 6.97 (m, 1 H) 7.07 – 7.1 1 (m, 1 H) 12.77 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BERTANI, Barbara; CREMONESI, Susanna; GARZYA, Vincenzo; MICHELI, Fabrizio; RUPCIC, Renata; SABBATINI, Fabio Maria; WO2011/151361; (2011); A1;,
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Reference of 16066-84-5, A common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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 1 Preparation of Compound c71 (0551) Compound c70 (1.0g, 4.15mmol) was dissolved in dioxane (16mL), and tertiary butyl methyl carbamate (653mg, 4.98mmol), 2- dicyclohexylphosphino-2 ‘, 4′ , 6’-triisopropyl-biphenyl (297mg, 0.622mmol), potassium phosphate (2.20g, 10.73mmol) and tris (dibenzylideneacetone) palladium (190mg, 0.207mmol) were added to the mixture at 100 C for 5 hours. Tertiary butyl methyl carbamate (218mg, 1.66mmol), 2-dicyclohexylphosphino-2 ‘, 4′, 6’-triisopropyl biphenyl (99mg, 0.207mmol), potassium phosphate (0.73g, 3.57mmol) and tris (dibenzylideneacetone) palladium (0) (63.3mg, 0.069mmol) were added to the mixture and the mixture was stirred for 3 hours. Tertiary butyl methyl carbamate (435mg, 3.32mmol), 2- dicyclohexylphosphino-2 ‘, 4′, 6’-triisopropyl biphenyl (99mg, 0.207mmol) and tris (dibenzylideneacetone) palladium (0) (63.3mg, 0.069mmol) was then added to the mixture and the mixture was stirred for 5.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give compound c71 (0.75g, 74% yield). [M + H] = 244.95, Method Condition 3: retention time 2.08 min

The synthetic route of 16066-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; KOBAYASHI, Naotake; ASAHI, Kentarou; TOMIDA, Yutaka; OHDAN, Masahide; FUMOTO, Masataka; SASAKI, Yoshikazu; KURAHASHI, Kana; INOUE, Takatsugu; URABE, Tomomi; NISHIURA, Yuji; IWATSU, Masafumi; MIYAZAKI, Keisuke; OHYABU, Naoki; WADA, Toshihiro; KATOU, Manabu; (276 pag.)EP3059225; (2016); A1;,
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Electric Literature of 19047-31-5,Some common heterocyclic compound, 19047-31-5, name is 2-Chloro-N-cyclopropylacetamide, molecular formula is C5H8ClNO, 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 2-chloro-N-cyclopropylacetamide (1.33 g, 10 mmol), 3- bromobenzenethiol (1.6 g, 8.5 mmol) and K2CO3 (4.8 g, 35 mmol) in 30 mL of acetone was heated at 70 C overnight. The mixture was filtered and concentrated to give a residue, which was purified by column chromatography (PE/EA, 1/1) to give the title compound (2.4 g, 96%) as a white solid. 1H NMR delta (300 MHz, CDC13) 7.39 (1H, m), 7.31 (1H, m), 7.14 (2H, m), 6.71 (1H, s), 3.58 (2H, s), 2.64-2.77 (1H, m), 0.73-0.84 (2H, m), 0.41 (2H, m); m/e 286 (M+H)+.

The synthetic route of 19047-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KADMON CORPORATION, LLC; BOXER, Michael; RYAN, John; TONRA, James; WO2014/55999; (2014); A2;,
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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. 67341-01-9, name is tert-Butyl (2-hydroxy-1-phenylethyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C13H19NO3

General procedure: To a solution of compound 4 (1 mmol) in CH2Cl2 (3 mL) wereadded trimethylamine (1.3 mmol) and methansulfonylchloride(1.1 mmol). After stirring at room temperature for 30 min, themixture was diluted with dichloromethane and washed withsaturated sodium bicarbonate solution. The organic layer was driedover sodium sulfate and filtered. After concentration, the filtratewas dried in vacuo to give compound 4a. The mixture of compound9 or 10 (1 mmol), the mesylate 4a (2.5mmol) and K2CO3 (5mmol) inDMF (10 mL) was stirred at 70 C overnight. The reaction mixturewas cooled to ambient temperature, diluted with ethyl acetate, andwashed with saturated ammonium chloride solution. The organiclayer was concentrated, then the residue was purified using silicagel and amine silica gel chromatography (hexane/EtOAc, 2:1). Thealkylated compound (1 mmol) in CH2Cl2 (40 mL) was treated withTFA (2 mL), stirring at room temperature for 3 h. The reactionmixture was neutralized with saturated NaHCO3 and extractedwith CH2Cl2 twice. The organic layer was concentrated, then purifiedusing silica gel chromatography (CH2Cl2/MeOH, 15:1-20:1).

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; Kim, Seon-Mi; Lee, Minhee; Lee, So Young; Lee, Soo-Min; Kim, Eun Jeong; Kim, Jae Sun; Ann, Jihyae; Lee, Jiyoun; Lee, Jeewoo; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 413 – 424;,
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Synthetic Route of 263349-73-1,Some common heterocyclic compound, 263349-73-1, name is 4-Bromo-3-fluorobenzenesulphonamide, molecular formula is C6H5BrFNO2S, 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 vessel was charged with 4-bromo-3-fluorobenzenesulfonamide (2, 255 mg, 1.00 mmol), Bis(pinacolato)diboron (280 mg, 1.10 mmol), Potassium acetate (295 mg, 3.01 mmol) and degassed dry 1,4-dioxane (5.02 mL). The vessel was evacuated and backfilled with argon (3x), XPhos Pd G4 (4.32 mg, 0.00502 mmol) was added and the mixture stirred at 85 C for overnight. After cooling to RT, the mixture was diluted with EtOAc and Acetic Acid (0.172 mL, 3.01 mmol), stirred for 30 minutes and filtered over Celite. The solvent was removed under reduced pressure. The residue was dissolved in a minimum amount of EtOAc, precipitated with n-heptane and the solids collected by suction filtration to yield 3-fluoro-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (220 mg, 0,7310 mmol, 73% yield) which was used without further purification. (0844) Analytical data: (0845) 1H NMR (200 MHz, DMSO) delta 7.91- 7.09 (m, 5H), 1.42- 0.95 (m, 12H); (0846) 13C NMR (50 MHz, DMSO) delta 148.6 (d, J = 8.2 Hz), 137.5 (d, J = 8.3 Hz), 121.05 (d, J = 2.1 Hz), 112.48 (d, J = 27.6 Hz), 83.9, 73.6, 25.0, 24.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-fluorobenzenesulphonamide, its application will become more common.

Reference:
Patent; HEPAREGENIX GMBH; PRAEFKE, Bent; KLOeVEKORN, Philip; SELIG, Roland; ALBRECHT, Wolfgang; LAUFER, Stefan; (157 pag.)WO2019/149738; (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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, A new synthetic method of this compound is introduced below., Safety of 1,1,1-Trifluoro-N-phenylmethanesulfonamide

To a solution of N-carbethoxy-4-tropinone (2-1) (15.0 g, 76.1 mmol) in 150 mL anhydrous tetrahydrofuran at-78 C was slowly added KN (TMS) 2 (182 mL, 0.5 ML in toluene). The solution was stirred at-78 C for 30 minutes, and then a solution of N-phenyltrifluoromethane sulfonamide (32.6 g, 91. 3 mmol) in 150 mL anhydrous tetrahydrofuran was added. The mixture was stirred at-78 C for 2 h and quenched with a saturated aqueous ammonium chloride (150 mL). After the removal of tetrahydrofuran under vacuum, the aqueous layer was then extracted with EtOAc (3 x 150 mL). The combined EtOAc layers were washed with IN KOH (150 ml), brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-30% ethyl acetate/hexanes as eluent) afforded (2-2) as a colorless oil.

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; MERCK & CO., INC.; WO2004/87159; (2004); A1;,
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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. 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: tert-Butyl 3-aminobenzylcarbamate

Example 2.4: tert-butyl 3-acetamidobenzyIcarbamate; [0235] To a stirred solution of tert-butyl 3-aminobenzylcarbamate (Hah, Jung-Mi; Martasek, Pavel; Roman, Linda J.; Silverman, Richard B.; J. Med. Chem.; 2003, 46,1661 – 1669) (287 mg, 1.29 mmol) in CH2Cl2 (10 mL) at O0C was added Et3N (0.27 mL, 2.0 mmol) and acetyl chloride (0.10 mL, 1.4 mmol) and the resulting solution was warmed up to room temperature slowly. After further stirring of 4 h, the reaction was quenched with saturated aqueous NH4Cl. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 x 20 mL). The combined organic layer was washed with H2O, brine, dried with Na2SO4 and concentrated under reduced pressure. The residue oil was purified by column chromatography (60% EtOAc in hexanes) to provide acetamide (123.1 mg, 36%).

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

Reference:
Patent; ZAPAQ, INC.; THE BOARD OF TRUSTEES OF THE UNVERSITY OF ILLINOIS; OKLAHOMA MEDICAL RESEARCH FOUNDATION; WO2006/110668; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4563-33-1, name is Phenylmethanesulfonamide, 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 4563-33-1, COA of Formula: C7H9NO2S

(b) tert-Butyl 3-[(benzylsuIfonyI)carbamoyl]azetidine-l-carboxylateTBTU (33.71 g, 105 mmol) and TEA (30.3 g, 300 mmol) was added to a solution of 1- (tert-butoxycarbonyl)azetidine-3-carboxylic acid from above (25.89 g, assumed to contain is 100 mmol) in THF (200 mL) and the reaction was stirred at r.t for 30 minutes. 1- phenylmethanesulfonamide (17.97 g, 105 mmol) and LiCl (1.844 g, 43.5 mmol) was added and the stirring was continued at r.t over night (23 hours). The reaction was concentrated to about 1/3 was left and EtOAc (500 mL) was added and the organic phase was washed with 2 M HCl (1 x 150 mL, 2 x 50 mL), water (2 x 50 mL). Drying (MgSO4), filtration and20 evaporation of the solvent gave a brown powder (48. 6 g). The powder was slurried in 150 mL TBME and stirred 3 hours. The solids was filtered off and washed with TBME (40 mL). This procedure was repeated twice with 100 mL TBME (washing with 25 mL) to give a brownish powder (33 g) still containing some HOBT. The powder was dissolved in about 100 mL warm EtOH and water (130 mL) was added to induce a crystallisation of the25 product. The crystals was filtered off and dried to give pure tert-butyl 3-[(benzylsulfonyl)carbamoyl]azetidine-l-carboxylate as an off white powder. Yield: 25.4 g(71%).1H NMR (400 MHz, DMSO-d6) delta 1.39 (9H, s), 3.30 (IH, m, overlapping with the watersignal in DMSO), 3.78-3.95 (4H, m), 4.73 (2H, s), 7.28-7.34 (2H, m), 7.36-7.41 (3H,30 m), 11.71 (IH, br s). MS m/z: 353 (M-I).

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, Phenylmethanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/4946; (2008); 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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C8H17NO3

(1) t-Butyl (2-hydroxyethyl)methylcarbamate (1.0 g) obtained by the method described in the literature (Synthetic Communications, 1993, p.2443) was dissolved in chloroform (5 ml), and a Dess-Martin reagent (2.54 g) was added to the solution under ice cooling. The resulting mixture was stirred at room temperature for 1.5 hours, then saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate were added to the reaction mixture, and the resulting mixture was stirred for 30 minutes. The reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain an aldehyde compound (1.21 g).

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; Taisho Pharmaceutical Co., Ltd.; Meiji Seika Kaisha, Ltd.; EP2287173; (2011); A1;,
Amide – Wikipedia,
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Related Products of 177906-48-8, A common heterocyclic compound, 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, molecular formula is C11H22N2O2, 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 33; {4-[3-(6-Bromo-pyridin-2-yl)- l-(2-trimethylsilanyl-ethoxymethyl)-lH-pyrazolo[3,4- d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester; The mixture of 3-(6-bromo-pyridin-2-yl)-6-chloro- l-(2-trimethylsilanyl-ethoxymethyl)- lH-pyrazolo[3,4-d]pyrimidine (from Example 31 supra) (2.65 g, 6.01 mmol), tert-butyl (lr,4r)- 4-aminocyclohexylcarbamate (1.53 g, 7.14 mmol) and Et3N (1.4 mL, 9.7 mmol) in IPA (60 mL) was heated at reflux for 16 hours. After cooling to room temperature, the reaction mixture was filtered and solid dried to give {4-[3-(6-bromo-pyridin-2-yl)- l-(2-trimethylsilanyl- ethoxymethyl)-lH-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as white powder. (Yield 3.3 g, 89%).

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; F. HOFFMANN-LA ROCHE AG; LIU, Wenjian; LUK, Kin-Chun Thomas; ZHANG, Xiaohu; WO2012/98068; (2012); A1;,
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