Tag: M.W=200-300

Electric Literature of 2982-54-9,Some common heterocyclic compound, 2982-54-9, name is 2-(4-(Benzyloxy)phenyl)ethanamine hydrochloride, molecular formula is C15H18ClNO, 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.

The free base was made by partitioning the solid between Et2O and 2 M aq. NaOH solution. The organic layer was washed with sat. aq. NaCl solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-(4-benzyloxyphenyl)ethyl amine as a white solid, 8.92 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-(Benzyloxy)phenyl)ethanamine hydrochloride, its application will become more common.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; Goff, Dane; Payan, Donald G.; Braselmann, Sylvia; US2013/237524; (2013); A1;,
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Application of 86770-76-5,Some common heterocyclic compound, 86770-76-5, name is 1-Phenyl-2,5,8,11-tetraoxatridecan-13-amine, molecular formula is C15H25NO4, 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: Tert-butyl alcohol (1.5 equiv.) was added drop-wise to a stirredsolution of chlorosulfonyl isocyanate (1 equiv.) in dry DCM (15 mL)at 0 C under nitrogen. The solution was stirred for a further30 min at 0 C before a solution of the amine (1 equiv.) and drytriethylamine (1.5 equiv.) in dry DCM (15 mL)was added drop-wise.The reaction mixture was allowed to warm to room temperature,and then stirred for 16 h. The reaction mixture was then dilutedwith DCM (20 mL), washed with saturated aqueous NaHCO3(3 20 mL) and brine (3 20 mL). The combined organic extractswere dried over anhydrous MgSO4, filtered, and concentrated invacuo to give a residue that was then purified by flashchromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Phenyl-2,5,8,11-tetraoxatridecan-13-amine, its application will become more common.

Reference:
Article; Suthagar, Kajitha; Watson, Andrew J.A.; Wilkinson, Brendan L.; Fairbanks, Antony J.; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 153 – 166;,
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Reference of 104566-41-8, 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 104566-41-8 as follows.

Another procedure involves use amide formation using the acid chloride as shown in the following reaction. To 4-biphenylacetic acid (2.5 g) in a flask, thionylchloride (20 ml) was added and heated to reflux for 1 h, cooled, and the excess thionylchloride removed under vacuum to dryness, then the produced crude acid chloride 2.8 g, dissolved in dry DCM (dichloromethane) (30 ml), and added drop wise at 0 C. to equimolar amount of the 3-benzyloxybenzylamine solution in DCM (10 ml) with (1.5 mol) of triethylamine (TEA) and stirred for 5 hrs, then poured onto acidified cold water, the organic layer washed with water, brine and the solvent removed under reduced pressure to give the target amide in 80% yield. 1H NMR (DMSO, 500 MHz): delta 8.58 (t, J=12 Hz 1H), 7.60-7.57 (m, 4H), 7.44-7.29(m, 10H), delta 7.21(t, J=16.5 Hz, 2H), 6.85(d, J=6.5 Hz, 2H), 6.81(d, J=8.0 Hz, 1H), 5.00(s, 2H), 4.24(d, J=6 Hz, 2H), 3.51(s, 2H).

According to the analysis of related databases, 104566-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangauer, David G.; US2006/160800; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6052-10-4, name is 4,4′-(Ethane-1,2-diylbis(oxy))dianiline, 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 6052-10-4, Recommanded Product: 6052-10-4

The TGAE was synthesized (Fig. 1.) according to the reported procedure [23]. A 250-mL two-neck round bottom flask, equipped with magnetic stirrer, thermometer and condenser was charged with 4-(2-(4-aminophenoxy)ethoxy)benzenamine ethane (5.0 g, 0.02 mol), 40 mLtoluene and 1.5 mL 50% manganese nitrate aqueous solution. The reaction mixture was stirred at 333 K for 50 min, and epichlorohydrin (9.63 mL, 0.12 mol) was added slowly. The reaction mixture was kept at 353 K for1 h; then 50% aqueous tetramethylammonium chloride (TMAC, 0.25 g, 0.00, 228 mol) and 3.65 g (0.091 mol) sodium hydroxide were added slowly in portions within 10 min. After addition, the temperature was maintained at 348-353 K and 12 mL distilled water was added, stirred and heated to separate out organic layers, which was washed with brine, separated and concentrated to get TGAE as a viscous brown liquid. 4-(2-(4-(bis(oxiran-2-ylmethyl)amino)phenoxy)ethoxy)-N,Nbis(oxiran-2-ylmethyl) benzenamine TGAE Colour, dark brown viscous liquid, EEW 170.8 g eq-1, Yield, 80%. FTIR (upsilon cm-1): 905 (C-O-C epoxide, asym), 810 (C-O-C epoxide, sym), 1223, 1067 (C-O, alkyl phenyl alcohol), 1375 (C-N ter. amine), 1507, 1456 (C=C aromatic), 2918 (C-H aliphatic), 1H NMR (300 MHz, CDCl3-d3): delta(ppm) = 2.8 (4H, m, 1a), 2.6 (4H, m, 1b), 3.2 (4H, m, 2), 3.7 (4H, m, 3a), 3.4 (4H, m, 3b), 6.8 (4H, dd, J = 9.3, 3.0 Hz, 4), 6.9 (4H, dd, J = 9.3, 2.4 Hz, 5) and 4.25 (4H, s,8). 13C NMR (300 MHz, CDCl3-d3): delta(ppm) = 45.37 (1), 47.18 (2), 50.74 (3), 114.8 (4), 116.4 (5), 151.3 (6), 143.4(7) and 67.4 (8).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,4′-(Ethane-1,2-diylbis(oxy))dianiline, and friends who are interested can also refer to it.

Reference:
Article; Siddiqi, Humaira Masood; Siraj, Amna; Khalid, Naila; Akhtar, Zareen; Zia Ul Haq, Muhammad; Journal of Thermal Analysis and Calorimetry; vol. 132; 1; (2018); p. 205 – 214;,
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Reference of 104750-60-9, A common heterocyclic compound, 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, molecular formula is C9H11BrO2, 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-Bromo-1-(methoxymethoxy)-4-methylbenzene (2.3 g, 9.95 mmol) from Example I-122A was dissolved in tetrahydrofuran (39.8 mL), and Q-Phos (1,2,3,4,5-pentaphenyl-1′-(di-tert-butylphosphino)ferrocene) (0.141 g, 0.199 mmol) and bis(dibenzylideneacetone)palladium (0.114 g, 0.199 mmol) were added. The reaction was sparged with nitrogen 10 minutes. A solution of freshly-prepared (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (45.2 mL, 19.91 mmol) in tetrahydrofuran was added dropwise. The reaction mixture was stirred at 50 C. for 30 minutes and at 45 C. for 15 hours. The reaction was cooled to ambient temperature and quenched with saturated aqueous ammonium chloride (40 mL). The mixture was diluted with methyl tert-butyl ether. The aqueous layer was extracted once with methyl tert-butyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by flash column chromatography, eluting with 0-20% ethyl acetate/heptanes to provide the title compound. 1H NMR (501 MHz, chloroform-d) delta ppm 7.06-6.99 (m, 2H), 6.97 (d, J=8.1 Hz, 1H), 5.16 (s, 2H), 3.60 (s, 3H), 3.45 (s, 3H), 2.28 (s, 3H), 1.63-1.57 (m, 2H), 1.12 (q, J=4.1 Hz, 2H)+

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; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 954235-78-0, name is 4-Bromo-2-(difluoromethoxy)-1-fluorobenzene, 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 954235-78-0, Recommanded Product: 954235-78-0

A 40-mL vial containing 4-bromo-2-(difluoromethoxy)-1-fluorobenzene (1.00 g, 4.15 mmol) (purchased from Combi-Blocks, Inc.), 1,1′-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (0.169 g, 0.207 mmol), bis(pinacolato)diboron (1.159 g, 4.56 mmol), and potassium acetate (1.222 g, 12.45 mmol) was flushed with N2 and subsequently charged with dioxane (4 mL). The slurry was stirred at 90 C. for 3.5 h. After cooling to rt, the reaction was quenched with H2O and extracted thrice with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a black oil. Column chromatography (25 g Snap Ultra column, 0% to 100% EtOAc/hept) afforded 2-(3-(difluoromethoxy)-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (178 mg, 0.618 mmol, 14.89% yield) as a brown-black oil. m/z (ESI) 289.2 (M+H)+.

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, 4-Bromo-2-(difluoromethoxy)-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
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Synthetic Route of 866633-25-2, 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 866633-25-2 as follows.

A solution of isopropylmagnesium bromide (2M solution in tetrahydrofuran) (83 ml, 0.166 mol) was added drop-wise to a stirred solution of 2-(trifluoromethoxy)-5-fluoro- 1 -bromobenzene (Preparation 49, 27.6 g, 0.107 mol) in anhydrous tetrahydrofuran (125 ml) at -1O0C under an atmosphere of nitrogen. The resulting mixture was stirred at room temperature for 2 hours. Tri/sopropyl borate (26.1 g, 0.139 mol) was then added drop-wise at -100C and the resulting mixture was stirred at room temperature for 16 hours. Hydrochloric acid (1 N aqueous solution) (100 ml) was added drop-wise at O0C and the mixture stirred at room temperature for 30 minutes. Ethyl acetate (150 ml) was added and the layers were separated, the aqueous layer was further extracted with ethyl acetate (2 x 150 ml). The organic extracts were combined and concentrated in vacuo. The residue was dissolved in potassium hydroxide (10% aqueous solution) (50 ml) and extracted with diethyl ether (2 x 150 ml). The separated aqueous layer was acidified to pH~4 by addition of hydrochloric acid (1 N aqueous solution) (100 ml) and extracted with ethyl acetate (3 x 150 ml). The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give an off white solid. Purification by preparative HPLC gave the title compound as an off white solid (5.82 g, 24%).1HNMR (cfe-DMSO): 7.23-7.32 (m, 3H), 7.53-7.55 (m, 1 H), 8.36 (br s, 1 H).MS m/z 223 [MH]-

According to the analysis of related databases, 866633-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
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Application of 1236000-51-3, 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. 1236000-51-3, name is N-Methyl-1-(4-(trifluoromethoxy)phenyl)methanamine hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 41 3-butyn-1-yl(methyl)({4-[(trifluoromethyl)oxy]phenyl}methyl)amine (N-methyI-N-({-4-[(trifluoromethyl)oxy]phenyl}methyl)-3-butyn-1-amine). To a solution of Intermediate 1 (0.480 g) in dry acetonitrile (6 ml) under N2 atmosphere were added K2CO3 (0.792 g) and Intermediate 40 (0.324 g) consecutively. The mixture was refluxed for 4 days, then concentrated to dryness under vacuum. EtOAc and H2O were added, the organic layer washed with H2O (2x) and brine (1x), then dried over Na2SO4. Elimination of the solvent under vacuum gave an oil which was purified by column chromatography on silica gel, eluting with a mixture 3% EtOAc/CH2CI2 to afford 0.18O g of the title compound as a colourless liquid.1H NMR (delta, ppm, CDCI3): 7.36 (d, 2H); 7.16 (d, 2H); 3.54 (s, 2H); 2.64 (t, 2H); 2.41 (td, 2H); 2.25 (s, 3H); 1.98 (t, 1 H). [ES MS] m/z 258 (MH+).

The synthetic route of N-Methyl-1-(4-(trifluoromethoxy)phenyl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BUENO-CALDERON, Jose Maria; FERNANDEZ-MOLINA, Jorge; LEON-DIAZ, Maria Luisa; MALLO-RUBIO, Araceli; MANZANO-CHINCHON, M Pilar; WO2010/81904; (2010); A1;,
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Application of 888318-22-7, 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. 888318-22-7, name is 1-Bromo-3,4-difluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Synthesis of 1-bromo-3,4-difluoro-2-methoxy-5-nitrobenzene Under a N2 gas blanket at room temperature, a solution of Tf2O (1 M in DCM, 7.5 mL) was added dropwise to a stirred suspension of tetramethylammonium nitrate (1.02 g, 7.5 mmol) in 7.5 mL of DCM. After stirring 1.5 h at room temperature, the stirred suspension was cooled to -78 C. To the stirred nitronium triflate suspension was added dropwise 3 dissolved in 2 mL of DCM. The cooling bath was then removed and allowed to warm to room temperature. The reaction mixture was quenched with saturated solution of NaHCO3. The solution was extracted with DCM (2×20 mL). The organic layers were combined, separated, dried over Na2SO4, and concentrated under vacuum. The residue was purified through column chromatography (eluent: hexanes/EtOAc=32/1) to afford YH10 as oil (720 mg, 54%). 1H NMR (300 MHz, CDCl3): 8.12 (ddd, J=5.0, 4.0, 2.5 Hz, 1H), 4.19 (d, J=1.2 Hz, 3H).

The synthetic route of 1-Bromo-3,4-difluoro-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
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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. 349-60-0, name is 1-Methoxy-3,5-bis(trifluoromethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Methoxy-3,5-bis(trifluoromethyl)benzene

In each of the examples in Table 3A, the substrate is reacted with the base in THF to form a metallic organoborate intermediate under the temperature and time conditions specified in Table 3A. The metallic organoborate intermediate is then reacted with the electrophile, E, in THF to form the functionalized products 11b to 11g under the following conditions:Furthermore, disubsituted anisole derivative such as lOf lead after metalation using 2b (25 °C, 0.5 h) followed by cross-coupling (ZnCl2 (10 molpercent), Pd(OAc)2 (3 molpercent), S-Phos (6 molpercent), 65 °C, 1 h) with 12 (0.8 equiv) to the functionalized anisole llf in 96percent yield (Table 3A, entry 6). In particular, tmpBEtyMgCl LiCl (2.2 mL, 1.0 M in THF, 2.2 mmol) was added dropwise at 25 °C to a solution of 3- bis(trifluoromethyl)anisole (lOf; 488 mg, 2.0 mmol) in THF (2 mL) in a flame-dried and Argon-flushed Schlenk-tube equipped with septum and magnetic stirring bar. After stirring for 30 min at 25 °C, ZnCl2 (0.2 mL, 1 M in THF, 10 molpercent), Pd(OAc)2 (14 mg, 3 molpercent), S-Phos (25 mg, 6 molpercent) and ethyl 4-iodobenzoate (12; 441 mg, 1.6 mmol) were added followed by continuously stirring for 1 h at 65 °C. After cooling to 25 °C, the reaction mixture was diluted with Et^O (5 mL) and quenched with sat. NH4C1 (aq.) (5 mL). The aqueous layer was extracted with CH2CI2 (3x 15 mL). The combined organic phases were dried over Na2SC>4 and the solvent was removed under vacuum. Flash column chromatography (pentane-Et^O, 95:5) afforded llf (602 mg, 96percent) as a white solid

The synthetic route of 349-60-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HAAG, Benjamin; WO2012/85169; (2012); A1;,
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