Tag: M.W=100-200

A common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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. 102-52-3.

5-Amino-1H-pyrazole-4-carboxylic acidEthyl ester (3.0 g, 19.3 mmol)In acetic acid (40 mL) and ethanol (10 mL)1,1,3,3-Tetramethoxypropane (3.48 g, 21.4 mmol) was added,The resulting reaction was stirred at 90 C overnight,Cool to room temperature,Concentrate under reduced pressure.The resulting residue was diluted with ethyl acetate (100 mL). The resulting solution was washed with saturated aqueous sodium bicarbonate (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (DCM / EA v / v) = 6/1) to give the title compound as a light yellow solid (3.2 g, 85%).

The synthetic route of 1,1,3,3-Tetramethoxypropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; (88 pag.)CN104650092; (2017); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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. 6851-80-5

Step B: To an ice-cooled mixture of the product from Step A (348 mg, 2.3 mmol) and diisopropylethylamine (394 mg, 3.0 mmol) in dichloromethane (10 mL) was added 1-(benzothiophen-5-yl)-2-bromo-ethanone (see Example 96 for preparation) (600 mg, 2.03 mmol). The reaction mixture was stirred at room temperature for 4 hours and then diluted with dichloromethane (100 mL). The mixture was washed with water and brine, dried over sodium sulfate and concentrated to provide the desired product (800 mg, >99% crude yield): ESI-MS m/z=326 [M+H]+. This crude product was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6851-80-5, its application will become more common.

Reference:
Patent; Molino, Bruce F.; Liu, Shuang; Guzzo, Peter R.; Beck, James P.; US2006/52378; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1758-46-9, Adding some certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, 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 1758-46-9.

To a stirred yellow solution of VII (371.8 mg, 1.089 mmol) in anhydrous THF (10 mL) was added 2-phenoxyethylamine (165 mg, 157 muL, 1,1×1.089 mmol) and then, dropwise, triethylamine (121 mg, 168 muL, 1.1×1.089 mmol). The solution was stirred for 1.5 hours at room temperature. The colorless solution was then diluted with CH2Cl2 and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (1:1, v/v) to yield 260.6 mg (67percent) of a 11 as a clear light yellow oil: Rf=0.39 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) delta 7.26 (td, 3J=8.0 Hz, 4J=1.1 Hz, 2H), 6.98 (d, 3J=8.0 Hz, 1H), 6.96 (m, 1H), 6.94 (d, 4J=1.0 Hz, 1H), 6.92 (dd, 3J=8.7 Hz, 1H), 6.86 (d, 3J=8.1 Hz, 2H), 5.21 (bs, 1H, NH), 5.06 (s, 2H), 4.03 (t, 3J=5.0 Hz, 2H), 3.80 (s, 3H), 3.59 (q, 3J=5.2 Hz, 2H, NCH2) and 2.29 (s, 3H). Exact mass (EST) calculated for C19H22NO6 [M+H]=360.1442. found 360.1443.

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 1758-46-9.

Reference:
Patent; Laskin, Jeffrey D.; Heck, Diane E.; Lacey, Carl Jeffrey; Aponte, Erik; Huang, Mou-Tuan; Heindel, Ned D.; US2012/59007; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

( 2R,6R, 1 lR)-tert-butyl 8-(( 2,4-dimethoxybenzyl)carbamoyl)-6, 11 -dimethyl-1, 2,5,6- tetrahydro-2, 6-methanobenzo[d]azocine-3( 4H)-carboxylate Chemical Formula: C 38N205 Exact Mass: 494.28 Molecular Weight: 494.62 To a solution of (2R,6R,1 lR)-tert-butyl 6,11 -dimethyl- 8- (((trifluoromethyl)sulfonyl)oxy)-l,2,5,6-tetrahydro-2,6-methanobenzo[d]azocine- 3(4H)-carboxylate (5.32 g, 11.8 mmol) in degassed dimethyl sulfone (50 mL), was added N-hydroxysuccinimide (2.73 g, 23.7 mmol), palladium acetate (265 mg, 1.18 mmol), triethylamine (3.3 mL, 23.7 mmol) and 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (683 mg, 1.18 mmol). The reaction mixture was heated with carbon monoxide (latm) at 70C overnight. The reaction mixture was cooled to ambient temperature and 2,4-dimethoxybenzylamine (2.17 mg, 13.0 mmol) added. The mixture was stirred for 2 hours diluted with ethyl acetate (800 mL), and filtered through celite. The organic solution was washed twice with water (800 mL), brine (300 mL), and dried (MgS04). Filtration and removal of the solvent under reduced pressure gave crude material that was purified by silica chromatography (EtOAc(l):heptanes(l)) to give (2R,6R,llR)-tert-butyl 8-((2,4- dimethoxybenzyl)carbamoyl)-6, 11 -dimethyl- 1 ,2,5,6-tetrahydro-2,6- methanobenzo[d]azocine-3(4H)-carboxylate (4.0 g, 68% yield); LC/MS(M+H)+ = 495.3.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ALKERMES PHARMA IRELAND LIMITED; BLUMBERG, Laura, Cook; DEAVER, Dan; EYERMAN, David; WO2014/190270; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

405-06-1, Adding some certain compound to certain chemical reactions, such as: 405-06-1, name is 2-Fluoro-4-methoxy-1-methylbenzene, 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 405-06-1.

A 10 mL oven-dried Schlenk tube was charged with magnesium (57.6 mg, 2.4 mmol) and anhydrous THF (1.5 mL), 5 drops of diisobutylaluminium hydride (DIBAL) was added and stirred for 5 min to activate magnesium. 2-bromo-1,3,5-triisopropylbenzene (566 mg, 2 mmol) was added potion-by-potion with vigorous stirring. The tube was capped with a rubber septum and was heated to 70 C. for 2 h (A). In another 10 mL oven-dried Schlenk tube was charged with 2-fluoro-4-methoxy-1-methylbenzene (140 mg, 1 mmol) and anhydrous THF (3.5 mL). The tube was cooled to -78 C. and 1.6 M n-BuLi solution in hexane (0.64 mL, 1 mmol) was added dropwise over 10 min under vigorous stirring. The mixture was stirred at -78 C. for 40 min (B). A was transferred into to B by syringe over 15 min at -78 C. An additional 1 mL of THF was used to rinse the reaction and was also transferred to B. The combined reaction mixture was stirred at -78 C. for another 1 h and then slowly warmed to room temperature and vigorously stirred for overnight. At this time, the mixture was cooled to 0 C. using ice bath, and iodine (762 mg, 3 mmol) in 4 mL anhydrous THF was added drop-wise over 5 min, then the reaction mixture was stirred for 30 min, and then warmed to stir at room temperature for 2 h. Then, the mixture was quenched with saturated Na2S2O3 (aq.) solution until the red color of bromine disappeared. The aqueous phase was extracted with Et2O (10 mL¡Á3) and the combined organic phases were dried over anhydrous MgSO4. After concentration, the crude product was purified by silica gel chromatography (EtOAc/petroleum ether=1/20) followed by crystallization in methanol to get a white solid (185 mg, 34%), labeled as 2MeO-SMeTIP-I. 1H NMR (600 MHz, Chloroform-d) delta 7.46-7.29 (m, 4H), 7.25 (dd, J=8.3, 0.8 Hz, 2H), 7.12 (s, 1H), 6.78 (d, J=8.3 Hz, 1H), 3.97 (s, 3H), 2.73-2.59 (m, 1H), 2.54 (p, J=6.8 Hz, 1H), 2.37 (p, J=6.8 Hz, 1H), 2.13 (s, 3H), 1.37 (d, J=7.0 Hz, 3H), 1.28 (d, J=6.8 Hz, 3H), 1.18-1.07 (m, 6H), 0.88 (d, J=7.2 Hz, 3H), 0.82 (d, J=7.2 Hz, 3H) ppm. 13C NMR (151 MHz, Chloroform-d) delta 156.49, 147.77, 146.49, 144.69, 141.28 (d, J=23.7 Hz), 139.64, 138.22, 131.97, 131.47, 130.62, 130.17, 129.81, 127.88, 126.87 (d, J=11.2 Hz), 126.38, 120.38 (d, J=35.2 Hz), 109.03, 56.39, 34.27, 32.38, 30.78, 30.26, 29.50, 24.63 (d, J=5.6 Hz), 24.47, 24.29, 24.22, 24.11, 23.42 (d, J=11.7 Hz), 21.54 ppm.

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 405-06-1.

Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 454-90-0 name is 3-(Trifluoromethyl)anisole, 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. 454-90-0

General procedure: (b) For isolations of the major products, copper(I) chloride (0.248 g, 2.5 mmol) and Mg powder (0.486 g, 20 mmol) were stirred in DMI (20 ml, 10 ml for 7i, 7j, 7k) and TMS-Cl (5 ml, 40 mmol) for 15 min under an argon atmosphere. Then, a benzotrifluoride derivative 6 (5 mmol) was added dropwise over 5 min into the dark suspension. The solution was stirred for additional time (see Table 2), keeping the temperature 25 C (bath temperature, 50 C for 7i, 7j, 7k). After addition of 5 ml of hexane, Mg-Cu was removed by decantation and the suspension was simultaneously extracted with hexane (5 ml¡Á5). Then, the combined hexane layer was washed with 10 wt % HCl aq and brine. After drying over sodium sulfate, purification by column chromatography on silica gel (hexane eluent) and distillation afforded the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)anisole, and friends who are interested can also refer to it.

Reference:
Article; Utsumi, Shinya; Katagiri, Toshimasa; Uneyama, Kenji; Tetrahedron; vol. 68; 4; (2012); p. 1085 – 1091;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20265-97-8, These common heterocyclic compound, 20265-97-8, name is 4-Methoxyaniline hydrochloride, 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.

p-anisidine hydrochloride (0.01 mol) was dissolved in a solution of concentrated hydrochloric acid (0.02 mol) in 50 ml of water. The mixture was cooled to 273 K on an ice water bath, and then sodium nitrite (0.015 mol) was dissolved in a small amount of water and added dropwise with vigorous stirring. The reaction mixture was stirred for1h, and then ethylenediamine dihydrochloride (0.0025 mol) was added. After the intense stirring for 10 min, KOH (0.04 mol) in 100 ml of water was added dropwise.The reaction took place immediately, and, as a result, the solution changed its color.The precipitate was collected by the vacuum filtration and dried at room temperature in vacuum. Yield 80%.1H-NMR (400 MHz, DMSO-D6, d, ppm) 7.50 (d, 8H, Ar), 6.90 (d, 8H, Ar), 3.84 (s,12H, -CH3), 3.1 (s, 4H, -CH2-) IR (KBr): 3000, 2934, 1602, 1504, 1448, 1248, 1028, 834

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 20265-97-8.

Reference:
Article; Vyshnevsky, Dmitry; Syromyatnikov, Vladimir; Kolendo, Alexey; Molecular Crystals and Liquid Crystals; vol. 672; 1; (2018); p. 73 – 80;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 5961-59-1, name is 4-Methoxy-N-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 5961-59-1

27.4 mg (0.2 mmol) of N-methyl-4-methoxyaniline, 81.2 mg of ethyl bromodifluoroacetate (0.4 mmol), 2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent. The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated. The solvent was removed and the residue was chromatographed on silica gel. It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1. The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator. Drying in vacuo to give the yellow liquid N-(4-methoxyphenyl)-N-methylformamide 26.4 mg, yield 80%.

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou University; Zhang Xiaohong; Li Xiaofang; Zhang Xingguo; (15 pag.)CN108774147; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., 768-70-7

At room temperature, FTA-Au(I)catalyst (2 mol%), AgOTf (5 mol%) was added to a stirring solution of 6a (1.0 mmol) in HOAc/H2O(10:1, 4 mL), then the reaction mixture was heated to 100 oC andstirred overnight (12 h). After the reaction completed, the solvent was removedunder reduced pressure and the residue was purified by flash chromatography onsilica gel (ethyl acetate/hexane = 1 : 80, V/V) to give the title compound 7a in 89% yield as light yellow oil.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Yao, Wei; Zhang, Yilin; Xu, Xiaqing; Yang, Yongchun; Zeng, Wei; Wang, Dawei; Journal of Organometallic Chemistry; vol. 901; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

702-24-9, 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. 702-24-9 name is 4-Methoxy-N-methylbenzylamine, 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.

3-( 5-amino-4-fluoro-2-methylphenyl)-7 -chloro-1-methyl-1 ,6-naphthyridin-2(1H)one(1.36 g, 4.28 mmol, 1.00 eq), 4-methoxy-N-methylbenzylamine (0.971 g, 6.42 mmol,1.50 eq) and DBU (0.960 mL, 6.42 mmol, 1.50 eq) were combined in NMP (20 mL) andheated at 180¡ãC under Ar overnight. The mixture was cooled to R T and poured onto H20(200 mL). The resulting solids were collected by filtration, rinsed very well with H20, driedon the filter to dampness and then dissolved in EtOAc. The solution was dried (MgS04),filtered and evaporated to afford 7-(( 4-methoxybenzyl)(methyl)amino )-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (1.86 g, 100percent yield) as a brittlebrown foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): 88.45 (s, 1H), 7.63 (s, 1H), 7.16 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 8.8 Hz, 2H), 6.86-6.82 (m,1H), 6.57 (d, J = 9.6 Hz, 1H), 6.29 (s, 1H), 4.88 (br s, 2H), 4.85 (s, 2H), 3.69 (s, 3H), 3.52 (s,3H), 3.07 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 433.3 [M+H(

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

Reference:
Patent; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2013/184119; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem