Tag: M.W=200-300

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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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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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. 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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Application of 174799-52-1, A common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, molecular formula is C14H22N2O2, 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.

41 c (5.00g, 17.96 mmol) and 56 (4.497g, 17.96 mmol, 1 eq) were dissolved in EtOH (30 mL) and a few drops of water added, before splitting the mixture into 2 x 30 mL W vessels. Each mixture was heated at 100 C for 30 mins in the MW reactor (dynamic program with maximum pressure 250 psi, maximum power 300W). Concentration of the reaction mixture gave approximately 10 g of crude residue. This was purified by FCC (eluent PE/DCM 1 :1 to prime/load the column, with the gradient increasing to 100% DCM over 5CV, 1 00% DCM for a further 3 CV and then raise to DCM/MeOH 99:1 over 1 CV, then to 95:5 over 3 CV, holding at this concentration to elute the desired product). This gave 7.30 (77%) g of white crystalline solid.

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; THE UNIVERSITY OF NOTTINGHAM; MISTRY, Shailesh; DARAS, Etienne; FROMONT, Christophe; JADHAV, Gopal; FISCHER, Peter Martin; KELLAM, Barrie; HILL, Stephen John; BAKER, Jillian Glenda; WO2012/4549; (2012); A1;,
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Reference of 112101-81-2,Some common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, 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 1: Preparation of 5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2- methoxybenzene-sulfonamide (Tamsulosin base)(R)-5-(2-arriinopropyl)-2-methoxybenzenesurfonarnide (60 g; 245.59 mmol) and l-(2- bromoethoxy)-2-ethoxybenzene (57.25 g; 233 mmol) were dissolved in 240 mL of N5N- dimethylformamide and 50.5 mL of diisopropylethylamine. The reaction mixture was heated to 100 C and stirred for 90 minutes. The mixture was then cooled to 20 C and 720 mL of ethyl acetate and 300 mL of water added to the vessel. The mixture was then stirred for 20 minutes at atmospheric condition, and then was allowed to settle. The aqueous layer was separated and re-extracted twice with 300 mL of ethyl acetate. The organic layers were combined and washed with 600 mL of water.The organic phase (1120 mL of ethyl acetate) was then concentrated by distillation at atmospheric pressure during which a white solid was precipitated. The mixture was then cooled to 2 C and stirred for 1 hour. The resulting crystals were isolated by filtration and washed with ethyl acetate to yield 133.59 g of wet tamsulosin base (Loss on Drying: 55.08% (corresponding to 60.01 g of dry material); HPLC Purity: 95.025%).EXAMPLE 3: Preparation of 5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2- methoxybenzene-sulfonamide (Tamsulosin base)(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide (100 g; 409.31 mmol) and 1- (2-bromoethoxy)-2-ethoxybenzene (95.4 g; 388 mmol) were dissolved in 400 mL of N,N- dimethylformamide and 84 mL of diisopropylethylamine. The reaction mixture was heated to 100 C and stirred for 90 minutes. The mixture was then cooled to 20 C, and 1200 mL of ethyl acetate and 500 mL of water were added. The mixture was then stirred for 20 minutes at atmospheric conditions and was allowed to settle. The aqueous layer was then separated and re-extracted twice with 500 mL of ethyl acetate. Next, the organic layers were combined and washed with 1000 mL of water.The organic phase (~1570 mL of ethyl acetate) was then concentrated by distillation at atmospheric pressure during which a white solid was precipitated. The mixture was then cooled to 2 C, and stirred for 1 hour. The resulting crystals were isolated by filtration and washed with ethyl acetate to yield 125.93 g of wet tamsulosin base (Loss on Drying: 24.09% (corresponding to 95.59 g of dry material); HPLC Purity: 97.62%). EXAMPLE 4: Preparation of 5-[(2R)~2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyI]-2- methoxybenzene-sulfonamide (Tamsulosin base)(R)-5-(2-arninopropyl)-2-methoxybenzenesulfonamide (3 g; 12.27 mmol) and l-(2- bromoethoxy)-2-ethoxybenzene (2.86 g ; 11.63 mmol) were dissolved in 12 mL of N5N- dimethylformamide and 2.55 mL of diisopropylemylamine. The reaction mixture was heated to 100 C and stirred for 90 minutes. The mixture was then cooled to 20 C, and 36 mL of ethyl acetate and 15 mL of water were added. The mixture was then stirred for 20 minutes at atmospheric conditions and was allowed to settle. The aqueous layer was then separated and re-extracted twice with 15 mL of ethyl acetate. Next, the organic layers were combined and washed with 75 mL of water.The organic phase (~80 mL of ethyl acetate) was concentrated by distillation at atmospheric pressure during which a white solid was precipitated. The mixture was then cooled to 2 C and stirred for 1 hour. The resulting crystals were isolated by filtration and washed with ethyl acetate to yield 5.14 g of wet tamsulosin base (Loss on Drying: 39.68% (corresponding to 3.1 g of dry material); HPLC Purity: 96.65%).The solid obtained in the previous step was then combined with 31 mL of ethanol. The reaction mixture was then heated to 78 C and stirred for 40 minutes, cooled to 0 C and stirred for 150 minutes. The resulting crystals were isolated by filtration to yield 4.92 g of wet tamsulosin base (Loss on Drying: 40.59% (corresponding to 2.81 g of dry material); HPLC Purity: 98.70%).

The synthetic route of 112101-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICHEM, S.A.; WO2007/119110; (2007); A2;,
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22117-85-7, name is 2-Methoxy-5-sulfamoylbenzoic acid, 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. category: amides-buliding-blocks

EXAMPLE 53 N-(1-Cyclohexyl-3-pyrrolidinyl)-2-methoxy-5-sulfamoylbenzamide To 3.7 g. (0.022 mole) of 3-amino-1-cyclohexylpyrrolidine in 100 ml. of pyridine was added dropwise with cooling 1.1 g. (0.008 mole) of phosphorous trichloride at 20C. After stirring one hour, 3 g. (0.013 mole) of 2-methoxy-5-sulfamoylbenzoic acid was added and refluxed 6 hrs. The solution was concentrated and the residue partitioned between dilute hydrochloride acid and isopropyl ether. The acid was made basic with ammonium hydroxide and extracted with chloroform which was dried (sodium sulfate) and concentrated. The residue was crystallized from ethyl acetate and recrystallized from isopropyl alcohol. Yield 1 g. (33%); m.p. 184-187C. Anaylsis: Calculated for C18 H27 N3 O4 S: C,56.67; H,7.13; N,11.02. Found: C,56.39; H,7.09; N,11.00.

The synthetic route of 22117-85-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; A. H. Robins Company, Incorporated; US3966957; (1976); A;,
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Application of 864448-41-9, These common heterocyclic compound, 864448-41-9, name is tert-Butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate, 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 a solution tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate (400mg, L75 mmol) and Et3N (0.49 niL, 3.5 mrnol) in DCM (10 mL) was added CbzCl (448 mg, 2.63 mmoi) at room temperature. The reaction mixture was stirred at room temperature for 2 hours and then water (10.0 mL) was added, and the mixture is extracted three times with EtOAc (30 rnL each). The combined organic phase was dried over Na2SO4 and concentrated. The residue was purifiedby silica gel colunm chromatography (PE: EtOAc, from 10:1 to 2: 1) to give a white solid (300 mg). The solid was dissolved in ACN (8 mL) and water (2 rnL), to which were added RuC13 (35 mg, 0.170 mmol) and Na104 (532 mg, 2.48 mmoi). The reaction mixture was stirred at room temperature for 36 hours and water (10 niL) was added, and the mixture was extracted three times with EtOAc (20 mL), The combined organic phase was dried over Na2SO4 andconcentrated. The residue was purified by column (PE: EtOAc, from 10:1 to 1: 1) to give the desired product 13a as a yellow oil (150 mg). LCMS (M-100+H) 277.1

The synthetic route of 864448-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; KOU, Buyu; LIU, Haixia; ZHANG, Zhisen; ZHOU, Zheng; (54 pag.)WO2018/11162; (2018); A1;,
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Application of 72505-21-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 72505-21-6 name is 4-(Trifluoromethyl)thiobenzamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A solution of 3-bromo-1-benzofuran-2(3H)-one (0.5 g,2.35 mmol) in toluene (5 mL) was added dropwise to a suspensionof the corresponding thioamide (2.35 mmol) and pyridine (65 mL,0.8 mmol) in toluene (5 mL) at room temperature. The reactionmixturewas stirred and heated at 80C for 2 h and then cooled. The amorphous precipitate was collected by filtration and thenrecrystallized from 80% aqueous ethanol to give products 1a-h as orange crystals. Alternative method for synthesis of 1a is alsodescribed in Ref. [25].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethyl)thiobenzamide, and friends who are interested can also refer to it.

Reference:
Article; Kammel, Richard; Tarabova, Denisa; Machalicky, Old?ich; Nepra?, Milo?; Frumarova, Bo?ena; Hanusek, Ji?i; Dyes and Pigments; vol. 128; (2016); p. 101 – 110;,
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Electric Literature of 27466-83-7, 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. 27466-83-7, name is 4-Bromo-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate Preparation 154′-(2-(S)-Pyrrolidin-ylmethyl-pyrrolidine-1-carbonyl)-biphenyl-4-carboxylic acid methylamide Procedure Z’: To a stirring solution of 4-bromophenylmethyl amide (11.0 mmol, CAS No. 27466-83-7), bis-(pinacolato)diboron (1.1 mmol) and potassium acetate (3.0 mmol) in dimethyl sulfoxide (0.10M), add palladium(II) dichloride (dppf) complex with dichloromethane (1:1) (0.08 mmol). Heat reaction to 100 C. for 1.5 hours. After this time, cool the reaction to room temperature and add (4-bromo-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone (the product from preparation 14) (1.0 mmol), 2M aqueous sodium carbonate (3.0 mmol) add palladium(II) chloride (dppf) complex with dichloromethane (1:1) (0.08 mmol). Heat reaction to 100 C. for 18 hours. After this time, remove the heat and wash the reaction with water while extracting with 10% isopropanol/dichloromethane. Dry the organics with sodium sulfate, filter and concentrate in vacuo. Purify the title compound via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 392.3 (M+1)

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

Reference:
Patent; Beavers, Lisa Selsam; Finley, Don Richard; Finn, Terry Patrick; Gadski, Robert Alan; Hipskind, Philip Arthur; Hornback, Wiliam Joseph; Jesudason, Cynthia Darshini; Pickard, Richard Todd; Takakuwa, Takako; Vaught, Grant Mathews; US2010/48580; (2010); A1;,
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