Tag: M.W=100-200

Electric Literature of 13304-62-6,Some common heterocyclic compound, 13304-62-6, name is N-Benzylacrylamide, molecular formula is C10H11NO, 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 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.

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

Reference:
Article; Zhang, Yikai; Lv, Zhiliang; Zhong, Hanyu; Zhang, Mingfeng; Zhang, Tao; Zhang, Wannian; Li, Ke; Tetrahedron; vol. 68; 47; (2012); p. 9777 – 9787;,
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Application of 5004-88-6,Some common heterocyclic compound, 5004-88-6, name is 2-Amino-4,5-dimethoxybenzamide, molecular formula is C9H12N2O3, 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 50 2-(4-(6,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)acetamide A solution of 4-hydroxy-3,5-dimethoxybenzaldehyde (1.0 g, 6.66 mmol) in DMF (10 mL) was cooled to 0 C. under nitrogen. NaH (0.4 g, 10 mmol, 60% in oil) was added portion-wise. The reaction was stirred for 30 min, then 2-bromoacetamide (0.918 g, 6.66 mmol) was added and stirring was continued for 36 h at room temperature. The DMF was removed under reduced pressure and water (50 mL) was added. The mixture was extracted with EtOAc (50 mL*3). The combined organic layers were washed with an aqueous solution of NaOH (50 mL, 10%), washed with water (50 mL) and brine solution (50 mL) and dried over MgSO4 and concentrated to give 0.6 g of crude intermediate, which was purified by flash column chromatography to provide the desired intermediate (366 mg, 26%), as a white solid. A mixture of 2-amino-4,5-dimethoxybenzamide (0.2 g, 1.019 mmol), 2-(4-formyl-2,6-dimethyl-phenoxy acetamide (0.211 g, 1.019 mmol), sodium hydrogensulfite (0.116 g, 1.121 mmol) and p-toluenesulfonic acid (20 mg) in N,N-dimethyl acetamide (5 mL) was stirred at 150 C. for 16 h under nitrogen. The reaction mixture was cooled to room temperature and water (50 mL) was added. The white precipitate was filtered off and washed with cold water (30 mL*2) and dried under high vacuum to provide 2-(4-(6,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)acetamide (300 mg, 76%) as a off white solid. Selected data: MS (ES) m/z: 384.1 (M+1); MP 354-356 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,5-dimethoxybenzamide, its application will become more common.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter Ronald; US2013/281397; (2013); A1;,
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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 142-26-7 as follows. Computed Properties of C4H9NO2

To a solution of 4-((2′, 3, 3′, 5-tetrafluoro-5′ -(anti-3-methoxycyclobutoxy)-[1, 1′-biphenyl]-4-yl)oxy)butanoic acid (56 mg, 0.13 mmol) in dry DCM (0.6 mL) was added thionyl chloride (19 muL, 0.26 mmol) at 0 C, stirred at 55 C for 8h. The reaction solvent was removed under reduced pressure. The crude product was dissolved in dry DCM (0.6 mL). The mixture was added N-(2-hydroxyethyl) acetamide (12 muL, 0.13 mmol), then was stirred at r.t. for 0.5-1h. Add triethylamine (46 muL, 0.065 mmol) to the reaction mixture stirred at r.t. for 3h. The reaction solvent was removed under reduced pressure to afford crude product. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 1 : 1 as eluent) to give 4-((2′, 3,3′,5-tetrafluoro-5′-(anti-3-methoxycyclobutoxy)-[1,1′-biphenyl]-4-yl)oxy)butanoate (18 mg, 27% yield) as colorless oil. 1H NMR (300 MHz, CDCl3) delta 7.16-6.99 (m, 2H), 6.65-6.56 (m, 1H), 6.54-6.51 (m, 1H), 5.86 (s, 1H), 4.83-4.76 (m, 1H), 4.29-4.15 (m, 4H), 4.15-4.07 (m, 1H), 3.54 (dd, J = 10.5 Hz, J = 5.5 Hz, 2H), 3.28 (s, 3H), 2.64 (t, J = 7.2 Hz, 2H), 2.51-2.36 (m, 4H), 2.17-2.07 (m, 2H), 2.00 (s, 3H); HRMS (ESI): Exact mass calcd. for C25H27F4NO6Na [M+Na] + 536.1672 found 536.16667.

According to the analysis of related databases, 142-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sheng, Ren; Yang, Liu; Zhang, Yanchun; Xing, Enming; Shi, Rui; Wen, Xiaoan; Wang, Heyao; Sun, Hongbin; Bioorganic and Medicinal Chemistry Letters; vol. 28; 15; (2018); p. 2599 – 2604;,
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2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, 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. SDS of cas: 2675-89-0

To a stirred mixture of 8-piperidin-4-yl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid (2-hydroxy-ethyl)-isopropyl-amide hydrochloride (127 mg, 0.23 mmol) in DMF (2 mL) was added potassium carbonate (127 mg, 0.92 mmol), N,N-dimethyl-2-chloroacetamide (36 mg, 0.3 mmol) and KI (catalytic) and stirring continued at RT for 72 h before concentrating in vacuo. The resultant residue was diluted with ethyl acetate and washed with water followed by brine, then dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was passed down an Isolute SCX-2 cartridge eluting with DCM/methanol then 2M NH3 in methanol. Basic fractions were combined and concentrated in vacuo, the residue subjected to RPHPLC (C18 column, gradient 5 to 95% CH3CN in water+0.1% HCO2H) to give 356 as a colourless glass (22 mg, 20%). LCMS: RT=1.90 min, [M+H]+=484 1H NMR 400 MHz (CDCl3) delta: 8.42 (2H, s), 8.20 (1H, br, s), 8.34 (1H, d, J=8.32 Hz), 7.81 (1H, s), 7.04 (1H, dd, J=8.40, 1.77 Hz), 6.90 (1H, d, J=1.69 Hz), 4.63 (2H, m), 4.45-4.44 (4H, m), 3.38 (3H, m), 3.32 (2H, m), 3.16 (2H, d, J=11.21 Hz), 3.11 (3H, s), 2.99 (3H, s), 2.56 (1H, m), 2.48 (2H, m), 1.87 (4H, m), 1.42 (6H, d, J=6.46 Hz)

The synthetic route of 2675-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blaquiere, Nicole; Do, Steven; Dudley, Danette; Folkes, Adrian; Heald, Robert; Heffron, Timothy; Jones, Mark; Kolesnikov, Aleksandr; Ndubaku, Chudi; Olivero, Alan G.; Price, Stephen; Staben, Steven; Wang, Lan; US2011/76292; (2011); A1;,
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Some common heterocyclic compound, 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, molecular formula is C11H12FNO, 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. Quality Control of 3-(4-Fluorophenyl)-N,N-dimethylacrylamide

General procedure: Cyanothioacetamide (for X=S) (1.5 equiv) or cyanoacetamide (for X=O) (1.5 equiv) was added to a solution of the 1, 3-diones (for R4= -CF3 and -CH3) (1.0 equiv) or enaminones (for R4=H) (1.0 equiv) in ethanol in the presence of DABCO (1.0 equiv) at room temperature. The reaction mixture was stirred under reux for 3-6 h until complete conversion of the starting materials, as monitored by TLC. After cooled to room temperature, the solvent was evaporated under reduced pressure and the residue was neutralized with diluted hydrochloric acid (1 N) to precipitate the crude products. After filtrated and dried in vacuo, the product can be straight used for step d. Yield: 70-90%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 75175-77-8, its application will become more common.

Reference:
Article; Wang, Ning-Yu; Zuo, Wei-Qiong; Xu, Ying; Gao, Chao; Zeng, Xiu-Xiu; Zhang, Li-Dan; You, Xin-Yu; Peng, Cui-Ting; Shen, Yang; Yang, Sheng-Yong; Wei, Yu-Quan; Yu, Luo-Ting; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1581 – 1588;,
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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. 39549-79-6, name is 2-Amino-4-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 39549-79-6

2-amino-4-methylbenzamide (4.93 g, 32.8 mmol) obtained in above was added with formic acid (30 mL, 787.9 mmol), followed by stirring for 6 hours at 100° C. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and washed with water. The filtered solid was dried with warm wind in an oven (40° C.) for 6 hours or more to obtain the title compound (4.79 g, 91percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 8.06 (s, 1H), 8.00 (d, 1H), 7.47 (s, 1H), 7.34 (d, 1H), 2.45 (s, 3H) MS (ESI+, m/z): 161 [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 39549-79-6.

Reference:
Patent; HANMI PHARM. CO., LTD; Bae, In Hwan; Son, Jung Beom; Han, Sang Mi; Kwak, Eun Joo; Kim, Ho Seok; Song, Ji Young; Byun, Eun Young; Jun, Seung Ah; Ahn, Young Gil; Suh, Kwee Hyun; US2014/371219; (2014); 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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl cyclopent-3-en-1-ylcarbamate

product was obtained which was recrystallised twice from heptane. After crystallization, 1.01 g of syn epoxide was obtained in the form of white needles. The mother liquors were subjected to chromatography (silica, toluene/EtOAc = 9:1 – 7:1) to yield 3.51 g of anti epoxide in the form of a white amorphous solid. [0058] Syn epoxide: is NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.36 (s, 9H), 6.79 (d, 1H, J=8Hz), 1.47 (dd, 1H, J=8Hz and 14Hz), 2.17 (dd, 1H, J=8Hz and 14Hz), 3.44 (s, 2H), 3.54 (m, 1H). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3:1, Rf = 0.4. [0059] Anti epoxide: 1H NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.35 (s, 9H), 1.78 (d, 2H, J=15Hz), 1.98 (dd, 1H, J=8Hz and 15Hz), 3.51 (s, 2H), 3.89 (q, 1H, J=8 and 16Hz), 5.70 (d, 1H, J=8Hz). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3:1, Rf = 0.45.

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; Nabriva Therapeutics AG; Mang, Rosemarie; Thirring, Klaus; Heilmayer, Werner; EP2433926; (2012); A1;,
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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. 116332-54-8, name is 4-Fluoro-N-methoxy-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Fluoro-N-methoxy-N-methylbenzamide

(b) 4-Fluoro-2-(4-pyridyl)acetophenone–A solution of lithium diisopropylamide was prepared at -78 C. in the usual manner from diisopropylamine (21 ml, 0.15 mol) and n-bultyllithium (54 mL of 2.5M solution in hexanes, 0.135 mol), and to this was added at -78 C., 4-picoline (10 g, 0.108 mol). After Stirring an additional 15 min at -78 C., 4-fluoro-N-methoxy-N-methylbenzamide (20 g, 0.109 mol) was added, and the mixture was allowed to slowly warm to rt. The reaction mixture was poured into saturated aqueous NaCl and extracted with 4:1 THF/CH2 Cl2, and the organic extract was dried (MgSO4). The solvent was removed in vacuo, and to the oily brown residue was added Et2 O. The title compound was obtained as a brown solid (16.8 g, 72%) which was recrystallized from Et2 O/Hex: 1 H NMR (CDCl3): d 8.55 (d, 2H); 8.03 (dd, 2H); 7.16 (m, 4H); 4.24 (s, 2H).

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 116332-54-8.

Reference:
Patent; SmithKline Beecham Corporation; US5916891; (1999); A;,
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Adding a certain compound to certain chemical reactions, such as: 25900-61-2, name is 3-Amino-N-methylbenzamide, 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 25900-61-2, Recommanded Product: 3-Amino-N-methylbenzamide

Step 4 Synthesis of 3-{2-[4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-acetylamino}-N-methyl-benzamide [4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-oxo-acetyl chloride (105 mg, 0.286 mmol) (prepared by the similar method described in example 57, Step-2 using 5-Fluoro-2-trifluoromethyl-phenyl)-piperazin-1-yl-methanone hydrochloride salt as starting material which is being prepared by the general method mentioned in the earlier examples using 5-fluoro-2-trifluoromethyl benzoic acid as starting material, Aldrich, St. Louis, Mo.) in DCM (2.5 mL) was added to cold(0 C.) solution of 3-Amino-N-methyl-benzamide (43 mg, 0.28 mmol), Et3N (86 mg, 0.12 mL, 0.86 mmol) in DCM (2.5 mL) and stirring was continued at ambient temperature for 2 hr. The reaction mixture was diluted with DCM, washed with cold water, followed by 2N HCl and brine solution. The organic layer thus collected was dried over sodium sulphate, concentrated under reduced pressure to afford the residue. The residue obtained was purified by recrystallisation from a mixture of ethyl acetate and hexane to afford 70 mg (51.09%) of 3-{2-[4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-acetylamino}-N-methyl-benzamide. LCMS Purity: 99.7%. 1H NMR (DMSO-d6): delta 10.95 (d, 1H), 8.4 (m, 1H), 8.2-8.0 (d, 1H), 8.6-7.9 (m, 1H), 7.8-7.6 (m, 1H), 7.6-7.4 (m, 4H), 3.9-3.4 (m, 6H), 3.3-3.1 (m, 2H), 2.8 (m, 3H).

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Reference:
Patent; Bischoff, Alexander; Subramanya, Hosahalli; Sundaresan, Kumar; Sammeta, Srinivasa Raju; Vaka, Anil Kumar; US2010/160323; (2010); A1;,
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Synthetic Route of 98-64-6, These common heterocyclic compound, 98-64-6, name is 4-Chlorobenzenesulfonamide, 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: The prepared TfOH-SiO2 (60 mg, containing 0.05 mmol TfOH) was added to the toluene (2 mL) solution of alkene (2 mmol or 4 mmol) and sulfonamide (1 mmol) and the reaction mixture was stirred at 70 oC (or 85 oC). The course of the reaction was monitored by TLC. After the completion of the reaction, the mixture was cooled to room temperature and the reactor was centrifuged (2000 r/min) for 2 min and the solution was removed by syringe. The catalyst was then washed with toluene (1 mL) twice with the same procedure and a new reaction was carried out by adding the new batch of alkene (2 mmol), sulfonamide (1 mmol) and toluene (2 mL) to the recovered catalyst. The solution containing the product was purified through a silica gel flash column to afford the product.

The synthetic route of 98-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Pei Nian; Xia, Fei; Zhao, Zheng Le; Wang, Qing Wei; Ren, Yu Jie; Tetrahedron Letters; vol. 52; 46; (2011); p. 6113 – 6117;,
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