Category: ethers-buliding-blocks

Electric Literature of 1535-75-7,Some common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, 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: General Procedure A: To a pressure tube containing ethyl 4,4,4- trifluoroacetoacetate (1.2 eq) and Eaton”s reagent [7.5% wt. phosphorous pentoxide p- toluenesulfonic acid solution ( 1 mL/0.3 mmol)], was added the corresponding aniline (1 eq). Then the pressure vessel was sealed and heated to 130 , and the reaction mixture was stirred overnight. After cooling to 0 C, the reaction was poured into ice water (~5 mL/1 mmol) and the solution pH was adjusted to 5 by the addition of saturated aqueous potassium carbonate. In situations when a pale yellow precipitate was formed, the solution was filtered and the residue was washed with water and cold ethanol, then dried in vacuo to yield the crude 4-hydroxyquinoline. Alternatively, the solution could be extracted with CHCl3 (20 mL x 3) and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo to give the crude 4-hydroxyquinoline. Then the residue was purified by column chromatography using hexane”EtOAc as an eluent (30% of EtOAc) to give the desired products with yields ranging from 45% to 60%. (0217) Characterization data for compound 1 and 1a e have been reported by Kozikowski. [0140] 8-trifluoromethoxy-2-trifluoromethyl-4-quinolinol (compound 1): Yield 51%.1H NMR (DMSO-d6) 7.19 (1H, s), 7.74 (1H, apparent t, J = 8.4 Hz), 7.88 (1H, d, J = 7.2 Hz), 8.28 (1H, d, J = 8.4 Hz), 9.71 (1H, br s).13C NMR (DMSO-d6) 101.5 (q, J = 2.4 Hz), 119.9, 120.8 (q, J = 258 Hz), 122.4 (q, J = 273 Hz), 123.5, 123.7, 127.3, 128.8, 141.8 (q, 1.8 Hz), 144.5 (q, J = 36 Hz), 163.9. UVmax: 294 nm, 303 nm, 315 nm

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

Reference:
Patent; THE TRUSTEES OF DARTMOUTH COLLEGE; CHEUNG, Ambrose Lin Yau; NAIR-SCHAEF, Dhanalakshmi R.; WU, Jimmy; CHEN, Ji; (73 pag.)WO2017/136642; (2017); A1;,
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Reference of 36805-97-7, The chemical industry reduces the impact on the environment during synthesis 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, I believe this compound will play a more active role in future production and life.

To a hot (80 C)solution of 4-bromo-3-methyl benzoic acid (3.00 g, 13.95 mmol) in toluene (250mL), N,N-dimethylformamide di-tert-butylacetal (11.35 g, 50.2 mmol) was added. The mixture was stirred at 80 C for 8 hand at rt for 16 h before another portion of N,N-dimethylformamidedi-tert-butyl acetal (5.67 g, 25.1mmol) was added. Stirring was continued at 80 C for 16 h. The mixture wascooled to rt, diluted with EtOAc and washed with sat. aq. NaHCO3-solutionfollowed by water. The org. layer was separated, dried over Na2SO4,filtered, evaporated and dried under high vacuum at 40 C to give tert-butyl 4-bromo-3-methyl benzoate(2.31 g, 61%) as a pale yellow oil; LC-MS: tR = 1.10 min, [M+1]+ = not detectable. 1HNMR (CDCl3): d 7.86(s, 1 H), 7.66 (d, J = 8.3 Hz, 1 H), 7.59 (d, J = 8.3 Hz, 1 H),2.46 (s, 3 H), 1.61 (s, 9 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, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lescop, Cyrille; Mueller, Claus; Mathys, Boris; Birker, Magdalena; De Kanter, Ruben; Kohl, Christopher; Hess, Patrick; Nayler, Oliver; Rey, Markus; Sieber, Patrick; Steiner, Beat; Weller, Thomas; Bolli, Martin H.; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 222 – 238;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 171290-52-1

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 ¡Á 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (3 mL) in the compound 7d (85.3 mg, 300 mumol),1-ethynyl -3,5-dimethoxy-benzene (121 mg, 750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. Using ascorbate (60.0 mg, 300 mumol) was prepared in the desired compound. The reaction mixture was stirred at 40 for 47 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 20: 1 CH2Cl2 / MeOH) to yield a compound 2d as a brown solid using (98.8mg, 74%) .

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 171290-52-1.

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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Application of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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.

b) 2-Methyl-2-{[1-(2-phenoxy-ethylamino)-naphthalene-2-carbonyl]-amino}-propionic acid3 mg copper(l)iodide, 127 mg potassium phosphate and 105 mg 2-[(1-bromo- naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester were placed in a reaction vial, which was evaporated and backfilled with argon three times. A solution of 62 mg 2-phenoxyethylamine and 12 mg N,N-diethylsalicylaminde in 0.5 ml of dry DMF was then added via septum. Under inert conditions the reaction mixture was heated to 1000C for 20 h. It was then diluted with ethyl acetate and water, the pH was adjusted to neutral, the layers were separated and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate and evaporated. After purification by RP-HPLC 12 mg 2-methyl-2-{[1-(2-phenoxy- ethylamino)-naphthalene-2-carbonyl]-amino}-propionic acid were obtained.C23H24N2O4 (392.46), LCMS (ESI): 393.16 (MH+).

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

Reference:
Patent; SANOFI-AVENTIS; WO2008/409; (2008); A1;,
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Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 163N-(2,2-diethoxyethyl)-5-{4-[4-({[(2-fluoro-5- methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamideA mixture of 5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2- yl}-1H-pyrrole-3-carboxylic acid (500mg, 1.12mmol), HATU (467mg, 1.23mmol) and N,N- diisopropylethylamine (322mg, 2.5mmol) in anhydrous DMF (10ml) was stirred at room temperature for 10 minutes, followed by addition of aminoacetaldehyde diethyl acetal (194mg, 1.46mmol). The mixture was stirred for another 10 minutes and poured into 100ml of water. The precipitates were filtered, washed with water and dried in vacuo to give N-(2,2- diethoxyethyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2- yl}-1H-pyrrole-3-carboxamide as white solid. Yield: 580mg, 92%. 1H NMR (DMSO-d6): 11.83 (br. s., 1H), 9.18 (s, 1H), 8.49 (d, J = 2.9 Hz, 1H), 8.38 (d, J = 5.6 Hz, 1H), 7.99 (dd, J = 7.9, 2.3 Hz, 1H), 7.94 (t, J = 6.0 Hz, 1H), 7.54 – 7.60 (m, 2H), 7.40 (dd, J = 3.1, 1.6 Hz, 1H), 7.10 – 7.19 (m, 4H), 7.08 (t, J = 2.2 Hz, 1H), 6.78 – 6.84 (m, 1H), 6.71 (dd, J = 5.6, 2.3 Hz, 1H), 4.56 (t, J = 5.6 Hz, 1H), 3.62 (dq, J = 9.7, 7.0 Hz, 2H), 3.47 (dq, J = 9.7, 7.0 Hz, 2H), 3.24 (t, J = 5.7 Hz, 2H), 2.28 (s, 3H), 1.11 (t, J = 7.0 Hz, 6H) LR MS (ES+): 562 (MH+) LR MS (ES-): 560 (M-H)

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLERGAN, INC.; GUO, Xialing; ZHU, Zhen; WO2015/69287; (2015); A1;,
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Electric Literature of 458-52-6, These common heterocyclic compound, 458-52-6, name is 2-Fluoro-4-methoxyaniline, 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.

Step C 2-Fluoro-4-methoxyphenyl isocyanate A solution of 8.8 grams (0.062 mole) of 2-fluoro-4-methoxyaniline in 70 mL of toluene was stirred, and a solution of 12.3 grams (0.062 mole) of trichloromethyl chloroformate in 30 mL of toluene was added dropwise. Upon completion of addition, the reaction mixture was warmed to reflux, where it was stirred for about 18 hours. After this time the reaction mixture was cooled and concentrated under reduced pressure, yielding about 10.4 grams of 2-fluoro-4-methoxyphenyl isocyanate. The product was used immediately in the next reaction.

The synthetic route of 458-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5399543; (1995); A;,
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Electric Literature of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3). 4.1.11.1. trans-N-(2-Phenoxyethyl)-3-phenyl-1,4-dioxane-2-carboxamide (26a). This compound was prepared starting from 24a and 2-phenoxyethanamine: a solid was obtained (73% yield;mp 109-110 C). 1H NMR (CDCl3) d 3.56 (m, 2H), 3.84e4.01 (m, 6H),4.08 (d, 1H, J 9.0 Hz), 4.42 (d, 1H, J 9.0 Hz), 6.60 (br t, 1H,exchangeable with D2O), 6.86e7.38 (m, 10H). ESI/MS: m/z 328.2[M H]. Anal. Calcd for C19H21NO4: C, 69.71%; H, 6.47%; N, 4.28%.Found: C, 69.87%; H, 6.23%; N, 4.39%.

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

Reference:
Article; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H14O3

Step A: Methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (922 mg, 3.6 mmol) from Step C of Example 13 was stirred in glacial acetic acid (2.5 mL) and(trimethoxymethyl)benzene (2.0 g, 10.9 mmol) at 70 0C for 3 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate) to give methyl l-(2,2- dimethoxyethyl)-2-phenyl-lH-benzo[J]imidazole-7-carboxylate as a brown oil (1.0 g, 83%): 1H NMR (500 MHz, CDCl3) delta 7.99 (d, J = 8.0 Hz, I H), 7.95 (d, J= 8.0 Hz, I H), 7.72-7.70 (m, 2H), 7.53-7.51 (m, 3H), 7.33 (t, J = 8.0 Hz, I H), 4.76 (d, J= 5.0 Hz, 2H), 4.24 (t, J= 5.0 Hz, I H), 3.99 (s, 3H), 3.07 (s, 6H); MS (ESI+) m/z 341 (M+H).

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; GUZZO, Peter, R.; MANNING, David, D.; EARLY, William; WO2011/8572; (2011); A2;,
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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. 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Methoxyethoxy)ethanamine

2.55 g (20 mmol) of oxalyl chloride are added to 10 g (16.5 mmol) of the title compound from Example 1a in 100 ml of dichloromethane and the mixture is stirred at room temperature for 14 h. It is evaporated to dryness in vacuo, the residue is dissolved in 100 ml of dichloromethane, 3.93 g (33 mmol) of 2-(methoxyethoxy)ethylamine (Whitesides et al., JACS, 1994, 5057-5062) are added and the mixture is subsequently stirred at room temperature for 4 h. The reaction solution is treated with 100 ml of 1 N hydrochloric acid, and thoroughly stirred for 15 min. The organic phase is separated off, dried over magnesium sulphate and evaporated to dryness in vacuo. The residue is chromatographed on silica gel (eluent: ethyl acetate/hexane 1:1). Yield: 11.2 g (96% of theory) of a colourless wax

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; Platzek, Johannes; Schirmer, Heiko; Weinmann, Hanns-Joachim; Misselwitz, Bernd; Zorn, Ludwig; US2008/159954; (2008); A1;,
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Reference of 6346-09-4, 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Under an argon atmosphere, a solution is prepared containing amino acetal (1.2 mmol) and triethylamine (2.0 mmol) in dry chloroform (10 mL). The mixture is cooled to 0 C and a solution of the acid chloride (1 mmol, in 5 mL of CHCl3) is added slowly with stirring. The mixture is allowed to warm to room temperature for 3 h. Following this reaction period, the mixture is extracted twice with chloroform. The organic extracts are then washed with 1 M HCl, with water, and twice with brine solution. After drying over anhydrous sodium sulphate, the organic solvent is removed by reduced pressure and the crude product is subject to column chromatography (SiO2, hexanes:ethyl acetate).

The chemical industry reduces the impact on the environment during synthesis 4,4-Diethoxybutan-1-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kennedy, Sean; Kethe, Anila; Qarah, Ahmad; Klumpp, Douglas A.; Tetrahedron Letters; vol. 59; 20; (2018); p. 1932 – 1935;,
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