Category: amides-buliding-blocks

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. 108448-77-7, name is (1R)-(+)-2,10,Camphorsultam belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: (1R)-(+)-2,10,Camphorsultam

EXAMPLE 3; (E)-3-Benzyloxypropenoyl-(2’S)-bornane-10,2-sultam (Scheme 3, 3-3); To a solution of (E)-3-benzyloxyacrylic acid (1.74 kg, 9.88 mol) and dichloromethane (20 L) is added thionyl chloride (1.75 kg, 14.7 mol) over a period of 30 min. The reaction mixture is heated at reflux and the SO2 and HCl generated are scrubbed through a solution of aqueous NaOH. After 4 h (reaction progress is monitored by 1H NMR analysis), the solvent is removed under vacuum and the residual thionyl chloride is removed under vacuum overnight to give 2.00 kg (104%) of the desired acid chloride 3-2. To a solution of camphor sultam (1.72 kg, 7.98 mol) in THF (16 L) at -40 C. is added methyl magnesium bromide (2.79 L, 8.38 mol; 3M solution in ether) at a dropwise rate while maintaining the internal temperature between -30 C. and -40 C. The reaction mixture is stirred for an additional hour at 40 C. To the anion at -40 C. is added slowly, acid chloride 3-2 (1.92 kg, 96% purity based upon the use of acid, 9.4 mol) in THF (8 L) while maintaining the internal temperature below -25 C. The reaction mixture is further stirred between -30 C. and -40 C. for 1 h and allowed to warm to +10 C. over a period of 5-6 h. The reaction mixture is then quenched with saturated aqueous NH4Cl (16 L). The aqueous layer is separated and extracted twice with ethyl acetate (10 L). The combined organic layers are washed with saturated aqueous sodium carbonate (20 L) and brine (20 L). The organic layer is filtered through a pad of anhydrous MgSO4 and concentrated under vacuum to dryness to furnish 3.12 kg of the crude product 3-3. The crude product is taken up in ethyl acetate (8.3 L) and heated to 60 C. to dissolve the crude residue. The homogenous solution is diluted slowly with hexanes (30 L) while maintaining the solution at reflux. The reaction mixture is kept in a cold room for 16 h at 4 C. The crystalline material that separated is collected by filtration and washed with hexanes to give 1.906 kg (60%) of the desired product 3-3. The filtrate also contains the product, but no attempts are made to recover this material from the filtrate.

The synthetic route of 108448-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BioCryst Pharmaceuticals, Inc.; US2006/128789; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 2895-21-8, These common heterocyclic compound, 2895-21-8, name is N-Isopropyl-2-chloroacetamide, 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 of 2-chloro-N-isopropylacetamide (201 mg, 1.48 mmol) in ethanol (1.73 mL) was added 4-bromo-o-anisidine (300 mg, 1.48 mmol) and potassium carbonate (615 mg, 4.45 mmol). The reaction mixture was then allowed to stir at 80 C overnight. The reaction was cooled to r.t. and concentrated under reduced pressure. The residue was taken up in EtOAc, and washed with NaOH (4.0 M). The aqueous layer was extracted with EtOAc (x3), the organic layers combined, washed with saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography eluting with 30-50% acetonitrile (0.1% formic acid additive) in water (0.1% formic acid additive) to yield 2-(4-bromo-2-methoxy-anilino)-N-isopropylacetamide (110 mg, 0.36 mmol, 25% yield) as a white solid. UPLC-MS (ES+, Method A): 1.65 min, m/z 301.2 [M+H]+.1H NMR (400 MHz, CDCl3) delta6.98 (dd, J = 8.3, 2.7 Hz, 1H), 6.90 (d, J = 2.0 Hz, 1H), 6.47-6.41 (m, 1H), 6.34 (d, J = 8.3 Hz, 1H), 4.18-4.08 (m, 1H), 3.87 (s, 3H), 3.73 (s, 2H), 1.11 (d, J = 6.6 Hz, 6H).

The synthetic route of 2895-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 782-45-6, 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. 782-45-6 name is 4-Amino-N-phenylbenzamide, 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 triphosgene (1 eq) in 5 mL dry THF was cooled to -78C. A solution of 4-(4-morpholin-4-yl-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine HCl salt (3 eq) and N,N-diisopropylethylamine (4.8 eq) in dry THF (5 mL) was added dropwis to the triphosgene solution. The mixture was warmed to room temperature and stirred for 50 min. A solution of the second amine (3 eq.) and N,N-diisopropylethylamine (2.5 eq) in dry THF (5 mL) was added dropwise. The reaction mixture was stirred for 48-72 h. The solvent was removed under reduced pressure then saturated aqueous sodium bicarbonate solution (5 mL) was added to the residue to neutralize any acid. Then the solvent was removed under reduced pressure. The crude product was dissolved in 3 mLof DMSO, filtered and purified reversed phase HPLC (15 min gradient acetonitrile in water, 0.1% trifluoroacetic acid or formic acid as a m odifier).The pure product was obtained as trifluoroacetate or formate salt.

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

Reference:
Article; Al-Ashmawy, Aisha A.K.; Ragab, Fatma A.; Elokely, Khaled M.; Anwar, Manal M.; Perez-Leal, Oscar; Rico, Mario C.; Gordon, John; Bichenkov, Eugeney; Mateo, George; Kassem, Emad M.M.; Hegazy, Gehan H.; Abou-Gharbia, Magid; Childers, Wayne; Bioorganic and Medicinal Chemistry Letters; vol. 27; 14; (2017); p. 3117 – 3122;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
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. 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,
Amide – an overview | ScienceDirect Topics

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;,
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. 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;,
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. 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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
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. 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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics