Month: August 2021

Application of 109903-35-7, A common heterocyclic compound, 109903-35-7, name is 4-Amino-N-methylbenzenemethanesulfonamide, molecular formula is C8H12N2O2S, 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.

N-Methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride A solution of 2-chloro-4-phenylamino-quinazoline (0.92 g) (prepared as described in Example 1a and N-methyl-(4-aminophenyl)-methanesulfonamide (0.80 g) in 10 ml of isopentylalcohol is stirred under nitrogen at 170 C. for 15 min in a sealed vessel. The warm reaction mixture is diluted with 10 ml ethanol and the hydrochloride salt, which is crystallizing on cooling, is filtered off to yield N-methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride as light yellow crystals melting at 259-263 C.; Rf (A2) 0.11, FAB-MS: (M+H)+ =420. Analytical data: C22 H21 N5 O2 S+HCl.

The synthetic route of 109903-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synaptic Pharmaceutical Corporation; US5968819; (1999); A;,
Amide – Wikipedia,
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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. 83948-54-3, name is tert-Butyl (5-bromopentyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Compound 5-1 (0.95 g, 4.29 mmol) was dissolved in N, N-dimethylformamide,Join in sequence5- (tert-butoxycarbonylamino) bromopentane(1.7 g, 6.43 mmol)And potassium carbonate (1.78 g, 12.9 mmol) were reacted at 90 C for 6 hours,The solvent was evaporated under reduced pressure, and ethyl acetate (40 ml) and water (30 ml) were added. After extraction, the organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and subjected to column chromatography to give compound 5-2 (1.6 g, Yield 89%).

The synthetic route of 83948-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Guangzhou Bio-pharmaceutical And Health Institute; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; China Pharmaceutical University; Jiang Sheng; Tu Zhengchao; Zhu Jidong; Yao Hequan; Yao Yiwu; Tan Xiaochu; Gu Shoulai; Qiu Yatao; (30 pag.)CN106928192; (2017); A;,
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Electric Literature of 4141-08-6, 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. 4141-08-6, name is 2-Amino-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.

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

Reference:
Article; Chen, Xiuling; Qi, Hongxue; Wu, Shaofeng; Liu, Leng; Wen, Jianhui; Li, Wanxi; Guo, Fang; Bian, Yongjun; Li, Jun; Heterocycles; vol. 94; 1; (2017); p. 86 – 94;,
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Electric Literature of 108468-00-4, 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 108468-00-4 as follows.

100 mg (0.109 mmol) of compound 3d was dissolved in 4 ml of DMF and cooled to -15 C. After addition of 36 tl (0.327 mmol) of NMM and 15 tl (0.109 mmol) CKIBE, the solution was stirred for 15 mm, followed by addition of 40mg (0.169 mmol) ofBoc-p-diaminoxylene and 12 tl (0.109 mmol) of NMM. The mixture was stirred for one hour at 0 C. and overnight at RT. The solvent was removed in vacuo, the residue was mixed with 1 ml 90% TFA and stirred for 2 h at RT. After removing the solvent in vacuo, the residue was dissolved in 8 ml of 30% B and purified by prep. HPLC (start at 10% B). Fractions containing the product were combined, the solvent was removed in vacuo and the residue dissolved in 80% t-butanol/water and lyophilized.jOllO] Yield: 39

According to the analysis of related databases, 108468-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHILIPPS-UNIVERSITAeT MARBURG; Steinmetzer, Torsten; Saupe, Sebastian; US2014/213781; (2014); A1;,
Amide – Wikipedia,
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Some common heterocyclic compound, 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, molecular formula is C7H6F3NO2S, 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. Formula: C7H6F3NO2S

Accurate weighing of the quinoline nitrogen oxides (44.3 mg, 0 . 25mmol), 4 – trifluoromethylbenzene sulfonamide (55.0 mg, 0 . 25mmol), double (trifluoroacetic acyloxy) iodobenzene (107.2 mg, 0 . 25mmol), 4 – N – morpholine – phenyl diphenyl phosphine (100.9 mg, 0 . 75mmol), and in turn to 25 ml of the bottle in the Schlenk, adding refined over-dimethyl sulfoxide (3.0 ml), is 120 C in oil bath reaction 30h. After the reaction, the solvent is removed under reduced pressure, the use of petroleum ether/ethyl acetate as eluant, separating by silica gel column, 4 – Trifluoromethyl – N – (quinolin – 2 – yl) benzenesulfonamide of yield is 67%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 830-43-3, its application will become more common.

Reference:
Patent; Dalian University of Technology; Yu Xiaoqiang; Bao Ming; Feng Xiujuan; Zhang Yue; Guo Mingju; (19 pag.)CN104447536; (2017); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 154748-63-7, A common heterocyclic compound, 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)carbamate, molecular formula is C9H17NO3, 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: To a solution of tert-butyl (1S,3R)-3-hydroxycyclopentylcarbamate (0.50g, 2.5mmol),4-(trifluoromethyl)phenol (0.49g, 3mmol) and triphenylphosphine (0.98g, 3.75mmol) in anhydrous THF (8mL) was dropwise added DIAD (0.98mL, 4.68mmol) in anhydrous THF (7mL). The reaction solution was stirred at room temperature overnight. The resulting solution was concentrated in vacuo, and the residue was subjected to flash column chromatography on silica gel (eluting with EtOAc-heptane by a gradient of EtOAc from 4% to 32%) to deliver title compound as colorless crystals (0.63g, 73%)

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; Aktas, Bertal H.; Bohm, Andrew; Chorev, Michael; Du, Ronghui; Halperin, Jose; Reis Monteiro dos Santos, Guilherme Rodrigo; Yefidoff-Freedman, Revital; Zhang, Qingwen; European Journal of Medicinal Chemistry; vol. 187; (2020);,
Amide – Wikipedia,
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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 144072-29-7 as follows. HPLC of Formula: C12H17NO3

To a solution of 31 (8.2 g, 36.7 mmol) in DCM (150 mL) were added TEA (11.1 g, 110 mmol) and MsCl (6.3 g, 55.1 mmol) at 0 C. The mixture was stirred at rt for 3 h, and quenched with water (80 mL), the aqueous layer was extracted with DCM (100 mL × 2), dried over Na2SO4, and concentrated under vacuum to yield crude 32 (7.5 g, 68%) as a yellow oil. This product was used in the following reaction without further purification

According to the analysis of related databases, 144072-29-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fujimoto, Jun; Hirayama, Takaharu; Hirata, Yasuhiro; Hikichi, Yukiko; Murai, Saomi; Hasegawa, Maki; Hasegawa, Yuka; Yonemori, Kazuko; Hata, Akito; Aoyama, Kazunobu; Cary, Douglas R.; Bioorganic and Medicinal Chemistry; vol. 25; 12; (2017); p. 3018 – 3033;,
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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. 214973-83-8, name is tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate, A new synthetic method of this compound is introduced below., Product Details of 214973-83-8

370 ml (350 mmol) of a 0.95 M sec-butyl lithium/n-hexane solution was added dropwise to a solution of 50 g (160 mmol) of 1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene (Reference Compound 4-1) in 800 ml of diethyl ether at -78 C. in an argon stream with stirring, and the mixture was stirred for 30 minutes. Then, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane was added dropwise thereto at -78 C. and the mixture was stirred at -50 C. for 2 hours. After the reaction was completed, 300 g of a saturated aqueous solution of ammonium chloride was added to the resulting solution, and 450 ml of water was poured into the solution to separate the mixture into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 100 ml of n-hexane was added to the resulting residue and the resulting solid was collected by filtration and successively washed with 100 ml of a mixed solvent (n-hexane:ethyl acetate=4:1 (v/v)) and 100 ml of n-hexane, whereby 33 g of the title compound was obtained as white powder (yield: 58%). Melting point: 142 to 144 C. Rf value: 0.38 (n-hexane:ethyl acetate=4:1 (v/v)) Mass spectrum (CI, m/z): 362 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)

The synthetic route of 214973-83-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Seike, Hisayuki; Matsugi, Takeshi; Shimazaki, Atsushi; US2009/12123; (2009); 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. 25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H7BrF3NO

A solution of 3-[3-(2-pyridinyl)phenyl]-1 ,4-diazaspiro[4.5]dec-3-en-2-one (D24) (21 mg) in DMF (4ml) was cooled to 00C. Sodium hydride (2.75mg of 60% in mineral oil, 0.069mmol) was added. The solution was stirred at 00C for 45 minutes before the slow addition (1 hr) of 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D8) (19.40mg) in DMF (1 ml) using a syringe pump. The resulting solution was allowed to warm to room temperature overnight and stirred for another 18 hours. The solution was then cooled again whilst stirring to 00C and sodium hydride (2.75mg, 0.069mmol) was added. Stirring continued for 45 minutes before the slow addition (1 hr) of 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D8) (19.40mg) in DMF (1 ml) using a syringe pump. The resulting solution was allowed to warm to room temperature and stirred over the weekend, then methanol (5ml) was added and the solution was evaporated to dryness, then re-dissolved in DCM (5ml) and water (5ml) was added. The resulting solution was poured through a phase separating cartridge and evaporated to dryness Purification using mass directed auto-purification chromatography gave the title compound as a white solid (22mg). 1H NMR (CD3OD) delta: 1.39-1.51 (3H, m), 1.81-1.91 (3H, m), 1.98-2.10 (assume 4H, m), 4.39 (2H, s), 7.37-7.41 (2H, m), 7.48-7.52 (1 H, t), 7.61-7.65 (1 H, t), 7.56-7.77 (1 H, d), 7.92-7.93 (2H, m), 8.01 (1 H, s), 8.12-8.15 (2H, m), 8.48-8.50 (1 H, m), 8.63-8.97 (1 H, m), 8.98 (1 H, s). Mass Spectrum (Electrospray LC/MS): Found 507 (MH+). C28H25F3N4O2 requires 506. Ret. time 3.14 min.

The synthetic route of 25625-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 56987-35-0, name is 3,3-Dibromo-azepan-2-one, 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. category: amides-buliding-blocks

A. 1-t-Butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one To a suspension of 300 mg of sodium hydride in 25 ml THF add a solution of 2.71 g of 3,3-dibromoperhydroazepin-2-one [R. Wineman et al., J. Am. Chem. Soc., 80, 6233 (1958)] and 2.50 g of t-butyl iodoacetate in 25 ml THF, carrying out the operation under N2. Stir the reaction at room temperature for several hours, quench with aqueous NaHSO3, isolate the organic phase, dry and concentrate in vacuo to obtain 1-t-butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one.

The synthetic route of 3,3-Dibromo-azepan-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US4409146; (1983); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics