Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, 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 956434-30-3, Safety of tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

(Step 1) A solution of the compound (0.300 g) obtained in Example 29, step 1, 2-methylpiperidine (185.7 muL), XPhos (0.030 g) and tBuONa (0.152 g) in toluene (10 mL) was degassed with argon gas, Pd2(dba)3 (0.019 g) was added, and the mixture was stirred at 100C for 1.5 hr under an argon atmosphere. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with water and brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 20?40% ethyl acetate/hexane) and recrystallized from pentane to give tert-butyl 8-(2-methylpiperidin-1-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.106 g, 29%) as a white powder. 1H-NMR(CDCl3): delta 1.12(3H,d,J=6.8Hz), 1.42(9H,s), 1.40-1.80(6H,m), 2.88(1H,dt,J=2.7,12.9Hz), 3.75-3.85(2H,m), 4.05-4.38(5H,m), 4.58(1H,brs like), 6.26(1H,d,J=8.3Hz), 7.60(1H,d like)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3144-09-0, name is Methylsulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methylsulfonamide

To a mixture of 5-chloro-2,4-dilfluorobenzoic acid (0.291 g, 1.51 mmol), EDCI (0.438 g, 2.29 mmol), and 4-dimethylaminopyridine (0.420 g, 3.44 mmol) in THF (5 mL) was methanesulfonamide (0.222 g, 2.33 mmol). After being stirred at room temperature for 18 h, the mixture was diluted with DCM (10 mL) and washed with 2 N HCl (15 mL*2). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford 5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide (0.388 g, 95% yield) as a white solid. LCMS (ESI) m/z: 268 [M-H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3144-09-0.

Reference:
Patent; XENON PHARMACEUTICALS INC.; GENENTECH, INC; Chowdhury, Sultan; Dehnhardt, Christoph Martin; Focken, Thilo; Grimwood, Michael Edward; Hemeon, Ivan William; Jia, Qi; Ortwine, Daniel; Safina, Brian; Sun, Shaoyi; Sutherlin, Daniel P.; Zenova, Alla Yurevna; US2013/317000; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 78888-18-3, The chemical industry reduces the impact on the environment during synthesis 78888-18-3, name is tert-Butyl allylcarbamate, I believe this compound will play a more active role in future production and life.

(20 g, 127.39 mmoL)Soluble in N,N-dimethylformamide (100mL),Sodium hydride (7.6g, 60%, 191.08mmoL)After treatment with n-hexane,Add N,N-dimethylformamide (400 mL),Under the protection of nitrogen,Add dropwise to the reaction solution at 0 C, and stir at 0 C for 30 minutes.The reaction was continued for 20 minutes at room temperature.Bromopropyne (30.3g, 245.78mmoL) was added dropwise under ice bath.Stir at 0 C for 30 minutes. The reaction solution was slowly added to crushed ice to treat excess sodium hydride.Extracted with ethyl acetate (100 mL ¡Á 3),The organic phases were combined and washed with saturated brine (100 mL¡Á3).Dry over anhydrous sodium sulfate, filter,The filtrate was concentrated under reduced pressure.The residue was purified by silica gel column chromatography ( petroleum ether / ethyl acetate (v/v) = 100:1 – 50:1) to afford(21 g, yield 85%).

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, tert-Butyl allylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Feng Jianchuan; Peng Fei; Chen Qingping; (45 pag.)CN105085530; (2019); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 402-46-0, name is 4-Fluorobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Fluorobenzenesulfonamide

Example 14 31. N-(4-fluorophenyl)sulfonyl-a-dehydrocyclohexylglycine.; 2-cyclohexyl-2-oxoethanoic acid (3.0 g, 19.2 mmol) was combined with p-toluenesulfonamide (2.70 g, 15.4 mmol) in toluene (21 mL) and diethyleneglycol diethyl ether (3 mL). MSA (0.10 mL, 1.5 mmol) was added, and this mixture was heated at reflux for 28h, then cooled to rt. The resulting solids were mixed with EtOAc (35 mL) and NaHC03 (2.6 g) in water (60 mL), until all materials dissolved. The aqueous was separated, and the organics were washed with NaH C03 (0.40 g) in water (10 mL). The combined aqueous layer was then washed with EtOAc (20 mL). The aqueous layer was cooled to 0 C, then treated with HCl (12.1 N, 3.1 mL). The resulting solids were filtered and washed with water and dried to give 3.0 g of crude material. The solids were then recrystallized from toluene/ methanol to give 2.8 g of white solid (58% yield). mp 214-215 C. ?H-NMR (400 MHz, CD30D) d 7.83-7.88 (m, 2H), 7.23-7.29 (m, 2H), 2.61-2.65 (m, 2H), 2.21-2.24 (m, 2H), 1.55-1.59 (m, 4H), 1.41-1.46 (m, 2H); ?3C NMR (100 MHz, CD30D) 167.2, 166.3,163.7, 155.3,136.5 (2 peaks), 129.9 (2 peaks), 118.3,115.5, 115.3,31.0, 30.5, 27.6, 27.2,25.7 ppm. HRMS calcd for C14H15FN04S (M-H) : 312.0706, Found: 312.0707.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 402-46-0.

Reference:
Patent; MERCK & CO., INC.; WO2005/118529; (2005); A2;,
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. 4943-86-6, name is 2-Amino-N-(4-chlorophenyl)benzamide, A new synthetic method of this compound is introduced below., COA of Formula: C13H11ClN2O

General procedure: A dry 50-mL flask was charged with 2-aminobenzamide 1 (1.0 mmol) and 1,2-dicarbonyl compound 2 (1.0 mmol), iodine (13 mg, 0.05 mmol), and [BMIm]Br (2.0 mL). The reaction mixture was stirred at 50 C under anhydrous atmosphere for 6-10 h. After the completion of the reaction as indicated by TLC [a small amount of reaction mixture was dissolved in EtOH, and the developing solvent is a mixture of ethyl acetate and petroleum ether (volume ratio 3:1)], 5 mL water was added to the mixture. The yellow precipitate was filtered off and purified by recrystallization from 95% EtOH to give final product 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:
Article; Wang, Jie; Zhang, Mei-Mei; Wang, Xiang-Shan; Research on Chemical Intermediates; vol. 43; 5; (2017); p. 2985 – 3005;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

(Step 1) A solution of the compound (0.285 g) obtained in Example 29, step 1, phenylboronic acid (0.183 g) and potassium carbonate (0.138 g) in a mixture of toluene (10 mL) and water (0.5 mL) was degassed with argon gas, tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.116 g) was added, and the mixture was stirred under argon atmosphere at 90C for 14 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 10?33% ethyl acetate/hexane) to give tert-butyl 8-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.040 g, 12%) as a white powder. 1H-NMR(CDCl3): delta 1.43(9H,s), 3.85-3.88(2H,m), 4.26-4.29(2H,m), 4.42-4.58(2H,m), 7.38-7.75(5H,m), 7.98(2H,d,J=7.2Hz)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 956434-30-3.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 683-57-8, 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. 683-57-8, name is 2-Bromoacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-bromo-2-hydroxybenzonitrile 1 (1O g, 50.5 mmol) in 50 mL acetone was added potassium carbonate (13.8 g, 100 mmol) and 2- bromoacetamide (6.9 g, 50.5 mmol). The reaction mixture was heated to 60 0C for 18 hours. After cooling, the solids were filtered off and dissolved in a large excess of water (1000 mL). The white solid was collected and dried to afford 11.2 g (89%) of 2- (4-bromo-2-cyanophenoxy)acetamide 2 as a white solid. 1H NMR (400 MHz, d6- DMSO): 8.03 (d, IH), 7.83 (dd, IH), 7.53 (br s, 1 H), 7.45 (br s, IH), 7.03 (d, IH), 4.7 (s, 2H).

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, 2-Bromoacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2009/86264; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 23530-40-7, A common heterocyclic compound, 23530-40-7, name is N-Methyl-2-nitrobenzenesulfonamide, molecular formula is C7H8N2O4S, 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.

2-Trityl-2H-tetrazol-5-ylmethanol (2.00 g, 5.84 mmol), N-methyl-2-nitrobenzenesulfonamide (1.64 g, 7.59 mmol) and triphenylphosphine (1.53 g, 5.84 mmol) were dissolved in a mixed solvent of tetrahydrofuran (30 mL) and toluene (20 mL), then a solution of diethyl azodicarboxylate in toluene (40%, 2.65 mL, 5.84 mmol) was added thereto and the mixture was stirred at room temperature for throughout a night. After the mixture was passed through a silica gel column (eluting solvent: ethyl acetate/hexane = 40/60) to remove original point components, acetone (5 mL) and acetonitrile (25 mL) were added to the residue prepared by concentrating in vacuo. Mercaptoacetic acid (0.73 mL, 11 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (3.1 mL, 21 mmol) were added to the resulting suspension and the mixture was stirred at 60C for 7 hours. The reaction solution was concentrated and the residue was dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated saline solution successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by a silica gel chromatography (eluting solvent: triethylamine/ethyl acetate = 1/99) to prepare N-methyl-N-(2-trityl-2H-tetrazol-5-yl)methylamine (396 mg, 1.11 mmol, yield: 19.0%). 1H NMR (CDCl3) delta(ppm): 2.45 (s, 3H), 4.07 (s, 2H), 7.07-7.36 (m, 15H).

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; KYOWA HAKKO KOGYO CO., LTD.; EP1547616; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 152192-95-5, name is tert-Butyl ethyl(2-hydroxyethyl)carbamate, 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 152192-95-5, COA of Formula: C9H19NO3

To a mixture of tert-butyl ethyl(2-hydroxyethyl)carbamate (1.89 g) obtained in Reference Example 19 and ethyl acetate (20 mL) were added acetic anhydride (1.04 mL), pyridine (0.89 mL) and 4-dimethylaminopyridine (0.061 g). After stirring at room temperature for 3 hrs., ethyl acetate (50 mL) was added, and the mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL). After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. A 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the residue, and the mixture was stirred at room temperature for 1 hr. Ethyl acetate (10 mL) and diethyl ether (20 mL) were added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.54 g) as a white solid.1H-NMR(DMSO-d6) : 1.22 (3H,t,J=7.3Hz), 2.07 (3H,s), 2.95(2H,q,J=7.3Hz), 3.15(2H,t,J=5.3Hz), 4.24-4.30(2H,m), 9.17 (2H,br).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl ethyl(2-hydroxyethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1607088; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 144912-84-5, 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. 144912-84-5 name is tert-Butyl (3-amino-2-hydroxypropyl)carbamate, 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.

The obtained crude product of ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester (283 mg, 1.487 mmol) and 5-[2-amino-6-(3-carboxylpropylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid tert-butyl ester (300 mg, 0.744 mmol) obtained in Step 1 of Example 2-1 were dissolved in N,N-dimethylformamide (7 ml), and then 1-hydroxybenzotriazole monohydrate (377 mg, 2.462 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (152 mg, 2.2 mmol) were sequentially added thereto. The resulting mixture was stirred at room temperature for three hours. The reaction solution was diluted with ethyl acetate, and then washed with a saturated aqueous ammonium chloride solution (twice) and a saturated aqueous sodium bicarbonate solution (twice). After the organic layer was dried over anhydrous sodium sulfate, the inorganic salt was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol = 20:1) to yield ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester. The obtained ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester was dissolved in dichloromethane (20 ml), and then water (0.1 ml) and trifluoroacetic acid (10 ml) were added thereto. After the solution was stirred at room temperature for one hour, the solvent was distilled off under reduced pressure to yield a crude product of 5-{2-amino-6-[2-((R)-3-amino-2-hydroxypropylcarbamoyl)ethylsulfanyl]pyrimidin-4-yl}-2,4-di methylbenzoic acid di(trifluoroacetate).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3-amino-2-hydroxypropyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; EP2119718; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics