Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, belongs to ethers-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 15799-79-8, Formula: C9H13NO

[0086] (R)-3-(4-Dimethylamino-2-methoxy-phenyl)-butyraldehyde (Table 1, entry 1). To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (12.3 mg, 0.050 mmol, 0.100 equiv), CH2Cl2 (0.50 ml), HCl (as a 4N solution in 1,4-dioxane, 12.5 uL, 0.050 mmol, 0.100 equiv), and N,N-dimethyl-m-anisidine (73.3 uL, 0.500 mmol, 1.00 equiv). The solution was cooled to -40o C. before crotonaldehyde (124 uL, 1.50 mmol, 3.00 equiv) was added. After 36 h, the reaction mixture was subjected directly to silica gel chromatography. Elution with 20% EtOAc in hexanes followed by concentration and removal of residual crotonaldehyde under vacuum afforded the product as a colorless oil in 86% yield (94.9 mg, 0.429 mmol); 89% ee. IR (film) 2958, 2874, 2834, 2719, 1721, 1615, 1568, 1516, 1462, 1441, 1352, 1238, 1133, 1034, 979.6, 814.0 cm-1; 1H NMR (300 MHz, CDCl3) ?9.67 (t, J=2.7 Hz, 1H, CHO), 7.03 (d, J=8.2 Hz, 1H, ArH), 6.31 (dd, J=2.5, 8.2 Hz, 1H, ArH), 6.27 (d, J=2.5 Hz, 1H, ArH), 3.83 (s, 3H, OCH3), 3.63 (dq, J=7.1, 7.1 Hz, 1H, ArCH), 2.94 (s, 6H, N(CH3)2), 2.68 (ddd, J=2.5, 6.9, 15.9 Hz, 1H, CH2CO), 2.55 (ddd, J=2.8, 7.7, 15.9 Hz, 1H, CH2CO), 1.27 (d, 3H, CHCH3); 13C NMR (75 MHz, CDCl3) ?203.7, 157.8, 150.9, 127.5, 121.7, 15.1, 96.6, 55.4, 51.2, 41.0, 27.6, 20.9. HRMS (CI) exact mass calcd for (C13H19NO2) requires m/z 222.1494 for [M+H]+, found m/z 222.1497. [?]D=-9.5 (c=1.0, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (3.0% ethanol/hexanes, 1 mL/min); S isomer tr=21.6 min, R isomer tr=23.1 min.

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; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10075-63-5, name is 1,5-Dimethoxynaphthalene, belongs to ethers-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 10075-63-5, Safety of 1,5-Dimethoxynaphthalene

General procedure: To [Ir(COD)OMe]2 (7.3 mg, 11 mumol) and 4,4′-di-tert-butyl-2,2′-bipyridine (7.0 mg, 26 mumol) in a flame-dried vial under nitrogen were added THF (0.7 mL), pinacolborane (0.18 mL, 1.24 mmol) and 1,4-dimethoxynaphthalene (7) (188 mg, 1.0 mmol). The mixture was stirred at 80 C for 24 h then filtered through Celite and concentrated in vacuo to afford crude pinacol ester 13 (100% conversion by 1H NMR) that was used directly in the next step.

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, 1,5-Dimethoxynaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hume, Paul; Furkert, Daniel P.; Brimble, Margaret A.; Tetrahedron Letters; vol. 53; 29; (2012); p. 3771 – 3773;,
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Reference of 17087-50-2, 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 17087-50-2 as follows.

In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the “dead time” to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode.

According to the analysis of related databases, 17087-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; ARMSTRONG, Daniel, W.; PING, Sun; BREITBACH, Zachary, S.; WANG, Chunlei; WO2010/148191; (2010); A2;,
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Reference of 6850-60-8, 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. 6850-60-8, name is (4-Ethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A corresponding primary amine (1.1 equiv.) and an excess of 37% formalinaldehyde free of paraformaldehyde (1.0 mL, 13.5 mmol) were added to a suspension of Guareschi imide triethylammonium salt 1a-c (0.8-0.9 mmol) in EtOH (6-12 mL). The mixture was refluxed for 3-5 min with stirring and allowed to stand for48 h at 20 C (precipitation of the corresponding “bispidinate”5a-m is possible). The mixture was acidified with 10% aqueousHCl to pH 3-4, after 1 day a precipitate formed was collected by filtration, washed with cold EtOH and diethyl ether, and, if necessary, recrystallized from the acetone-EtOH solvent system

The chemical industry reduces the impact on the environment during synthesis (4-Ethoxyphenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chigorina; Frolov; Dotsenko; Goloveshkin; Bushmarinov; Krivokolysko; Russian Chemical Bulletin; vol. 65; 9; (2016); p. 2260 – 2269; Izv. Akad. Nauk, Ser. Khim.; 9; (2016); p. 2260 – 2269,10;,
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Reference of 131713-50-3, 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. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[(3 S)-(7-BroMo-2-oxo-5-pyridin-2-yl-2, 3 -dihydro- 1H-benzo[e] [1,4] diazepin-3 -yl)-propionic acid Methyl ester (Compound of formula TV, S enantiomer,25.0 gr) and dichloromethane (?IVIDC?, 375 ml) were charged into a clean, dry 4 neck RBF. The reaction mixture was stirred for 5-10 minutes at temperature of 20-25C and a clear solution was obtained. 2-bromo pyridine (29.46 gr) was added to the solution and the obtained reaction mixture was stirred for 5-10 minutes. The obtained reaction mass was cooled down to a temperature of -15 to -20C. Then, Triflic anhydride (26.32 gr) was slowly added, over a period of 30-45 minutes to the cooled reaction mass, at the same temperature of-15 to -20C. After the addition was completed, the obtained reaction mixture was stirred for 30-45 minutes, at the same temperature of -15 to -20C. The reaction progress was monitored by HPLC (monitor intermediate (S)-3 -(2-(methoxycarbonyl)ethyl)-7-bromo-5 – (pyridin-2-yl)-3H-benzo [e] [1,4] diazepin-2-yl trifluoromethanesulfonate formation). Afterwards, 1-amino-2,2-dimethoxypropane (14.81 gr) in dichloromethane (2 vol, 50 mL) solution was slowly added over a period of about 30 minutes to the reaction mixture at temperature of -15 to -20C. After complete addition, Triethylamine (31.44 gr) was slowly added over a period of about 30 minutes at the same temperature of -15 to -20C, and the obtained mixture was stirred at temperature of -15 to -20C for 60-120 minutes. The reaction progress was monitored by HPLC. After the reaction was completed, ammonium chloride solution (20%, 125 ml) was added, and the temperature was raised to 15-20C; the obtained mixture was stirred for 30 minutes. The organic layer was separated, washed with DM water (125 ml) and re-separated. The organic layer was then concentrated to volume of 1-1.5 vol, at a temperature below 45C. Toluene (50m1) was added to the reaction mass, and then stripped out 1 vol under vacuum at a temperature below 60C. Then, Toluene (50m1) was added and the obtained mixture was heated to temperature of 60-65C, and was stirred at this temperature for 30-45 minutes. Heating was discontinued and the reaction mass was slowly cooled to temperature of 0-10C, and was stirred for 3-4 hours – crystallization occurred. The obtained suspension was stirred at temperature of 0-10C for 3 0-45 minutes. The obtained solid was filtered and washed twice with pre-cooled (temperature of about 5-10 C) toluene (12.5 ml X 2 times), and suck-dried for 20-30 minutes. The wet solid was further dried under vacuum at temperature of 40-45C for 6-8 hours. Yield (dry): 26.5 gm (85%)

The synthetic route of 2,2-Dimethoxypropan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WATSON LABORATORIES INC.; BEN-ZION, Dolitzky; MARIOARA, Mendelovici; RAJARAM, Bodkhe Arjun; SHIVAJI, Mane Ganesh; SRIHARI, Samala Rajamouli; VIJAY, Joshi Ashutosh; LUTHRA, Parven Kumar; SINGH, Amit; MUTHUSAMY, Anantha Rajmohan; (62 pag.)WO2018/148361; (2018); 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 1187160-18-4 as follows. name: 7-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride

To a stirred solution of ethyl 4-chloro-2-methyIthiopyrimidine-5-carboxylate (2.24 g, 9.62 mmol) in 35 mL of anhydrous tetrahydrofuran was added triethylamine (4.00 mL, 2.90 g, 28.72 mmol). The solution was cooled to 0-5 0C and 7-methoxy-l -aminoindane hydrochloride (2.00 g, 10.01 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred 48 h. The precipitate was filtered off, washed with ethyl acetate (1 x 25 mL), and the combined filtrates were evaporated to dryness. The residue was dissolved in dichloromethane (35 mL) washed with saturated sodium bicarbonate solution (1 x 17 mL), dried over magnesium sulfate, filtered and concentrated to give 4-(7-methoxy- 2,3-dihydro-l H-inden-l -ylamino)-2-(methylthio)pyrimidine-5-carboxylate as an oil (3.31 g, 9.21 mmol, 95%). ESMS m/z 360 (M+H)+; 1H NMR (400 MHz, CDCl3) delta ppm 8.63 (s, I H), 8.43 (d, J = 6.5 Hz, I H), 7.21 – 7.26 (m, I H), 6.88 (d, J= 7.5 Hz, I H), 6.72 (d, J= 8.3 Hz, I H), 5.69 – 5.78 (m, IH), 4.26 (q, J= 7.2 Hz, 2H), 3.78 (s, 3H), 3.01 – 3.13 (m, I H), 2.82 – 2.94 (m, I H), 2.59 – 2.67 (m, I H), 2.56 (s, 3H), 2.04 – 2.14 (m, IH), 1.33 (t, J= 7.2 Hz, 3H).

According to the analysis of related databases, 1187160-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio G.; VOLLRATH, Benedikt; WADE, Warren; WO2010/71846; (2010); A2;,
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Reference of 82830-49-7, These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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-fluoro-1,4-dimethoxybenzene(18) (3.9 g, 24.9 mmol) in anhydrous THF (150 mL) under argon at -78 C was added n-BuLi(1.6 M in hexane, 18.7 mL, 29.9 mmol) dropwise via syringe. The reaction mixture was stirredunder argon at -78 C for 1 hour and methyl chloroformate (2.30 mL, 29.9 mmol) was thenadded dropwise via syringe. The reaction mixture was stirred under argon at -78 C for another4 hours. Upon completion, the reaction mixture was quenched with water (10 mL) and extractedwith EtOAc (2 x 50 mL). The combined organic layers were washed with water and brine, driedover MgSO4, filtered, and concentrated by rotary evaporation. Purification by flash columnchromatography (silica, 9% EtOAc-hexane) gave methyl 2-fluoro-3,6-dimethoxybenzoate (5.2 g,96%) as a colorless oil. methyl 2-fluoro-3,6-dimethoxybenzoate: Rf = 0.15 (25% EtOAc-hexane); 1H NMR (400 MHz, CDCl3) delta 6.94 (t, J = 9.2 Hz, 1H), 6.59 (d, J = 9.2 Hz, 1H), 3.90 (s,3H), 3.81 (s, 3H), 3.77 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 164.0, 151.2, 150.9, 148.7, 141.7,115.5, 106.1, 57.0, 56.4, 52.6; HRMS calc. for C10H11FO4Na (M + Na)+ 237.0534, found237.0535.

Statistics shows that 2-Fluoro-1,4-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 82830-49-7.

Reference:
Article; Chantarasriwong, Oraphin; Milcarek, Andrew T.; Morales, Theodore Habarth; Settle, Aspen L.; Rezende, Celso O.; Althufairi, Bashayer D.; Theodoraki, Maria A.; Alpaugh, Mary L.; Theodorakis, Emmanuel A.; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 405 – 413;,
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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. 4457-67-4, name is 1-Bromo-4-methoxybutane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-4-methoxybutane

d) Benzyl (3R,4R,5S)-3-hvdroxy-4-[4-(4-methoxy-butoxy)phenvH-5-thiso- propylsilanyloxy-piperidine-1-carboxylate; Analogously to method F, starting from benzyl (3R,4R,5S)-3-hydroxy-4-[4- hydroxyphenyl]-5-triiso-propylsilanyloxypiperidine-1 -carboxylate [873945-27-8] and 1 -bromo-4-methoxybutane [4457-67-4] the title compound is obtained as a yellow oil. Rt = 6.63 (gradient I).; General method F: (phenol alkylation I); The mixture of 20 mmol of “phenol” in 60 ml of N,N-dimethylformamide is stirred with 4.15 g of potassium carbonate and 30 mmol of “halide” or “tosylate” for 24 hours at 1000C. The reaction mixture is then evaporated. The residue is treated with 1 M aqueous sodium hydrogencarbonate solution (40 ml) and extracted with ethyl acetate (2 X 60 ml). The organic phases are washed with brine (1 X 60 ml), dried using sodium sulphate and evaporated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

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 4457-67-4.

Reference:
Patent; Speedel Experimenta AG; WO2008/17685; (2008); A1;,
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Electric Literature of 2338-54-7, 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. 2338-54-7, name is 4-Fluoro-3-methylanisole, This compound has unique chemical properties. The synthetic route is as follows.

To a 250 mL three-necked flask was added 1-fluoro-4-methoxy-2-methylbenzene (18.3 g, 130.6 mmol)Under ice-cooling, sulfonyl chloride (27.4 g, 235.0 mmol) was slowly added dropwise and reacted at room temperature for 2 h. After completion of the reaction, the reaction solution was poured into ice water and analyzed.A large amount of solid was added, and the filter cake was dried in vacuo to give 23.2 g of 5-fluoro-2-methoxy-4-toluenesulfonyl chloride in 74.5% yield.

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-methylanisole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guizhou University; Liu Li; Quan Wen; Zhang Menghui; Huang Zhuyan; (6 pag.)CN106674065; (2017); A;,
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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. 4457-67-4, name is 1-Bromo-4-methoxybutane, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-4-methoxybutane

A solution of 4-methoxybutyl bromide (4.5 g) in acetonitrile (15 ml) is added dropwise under reflux to a mixture of salicylic acid ethyl ester (2.63 ml), powdered potassium carbonate (3.10 [G)] and potassium iodide (10 mg) in acetonitrile (50 ml), and the reaction mixture is then stirred overnight. After cooling, filtration is carried out, the filtrate is concentrated and the residue is added under a high vacuum. The title compound (4.4 g), Rf (C) =0.28, is obtained in the form of a pale-yellow 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; ELAN PHARMACEUTICALS, INC.; WO2003/103652; (2003); A1;,
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