Category: ethers-buliding-blocks

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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Reference of 2186-92-7, A common heterocyclic compound, 2186-92-7, name is P-anisaldehyde dimethyl acetal, molecular formula is C10H14O3, 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: Under an atmosphere of argon, to a mixture of benzaldehyde (0.213 g, 2.0 mmol) and Al-MCM-41 (60 mg, dried prior to use at 120C for 1 h under vacuum) in acetonitrile (3.0 mL), 1-phenyl-1-trimethylsiloxyethene (0.462 g, 2.4 mmol) in acetonitrile (3.0 mL) was added through a syringe at 0C. The reaction mixture wasstirred at 0C for 15 min. The catalyst was removed by filtration and washed with Et2O (40 mL). After the filtrate was concentrated under reduced pressure, crude product was purified by silica-gel column chromatography (hexane/Et2O 20:1) to give 1,3-diphenyl-3-trimethylsiloxypropan-1-one as a colorless oil (0.591 g, 99%). The recovered catalyst was dried at 70C for 15 min. The catalyst (47 mg) was then dried at 120C for 1 h under vacuum and used in a second run.

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:
Article; Ito, Suguru; Tanuma, Kenji; Matsuda, Kohei; Hayashi, Akira; Komai, Hirotomo; Kubota, Yoshihiro; Asami, Masatoshi; Tetrahedron; vol. 70; 45; (2014); p. 8498 – 8504;,
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Synthetic Route of 38603-09-7, A common heterocyclic compound, 38603-09-7, name is 1,3-dibromo-2-methoxybenzene, molecular formula is C7H6Br2O, 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.

Example 21 Preparation of (3-Bromo-2-methoxyphenyl)-(2-methoxyphenyl)methanol 2,6-Dibromoanisole (138.0 g, 0.51 mol) was dissolved in 750 ml of tetrahydrofuran and the solution cooled to -63 C. Butyl lithium (319 ml of 1.6 M, 0.51 mol) was added slowly with stirring and the mixture stirred at -60 C. for 4.5 hours and then 69.4 g (0.51 mol) of o-anisaldehyde in 250 ml of tetrahydrofuran was added slowly with stirring and the mixture allowed to stir cold for 1 hour. The mixture was allowed to warm to ambient temperature and was then poured into a mixture of ice and saturated aqueous ammonium chloride. The resulting mixture was extracted with ether and the ether extract dried over magnesium sulfate and then concentrated by evaporation under reduced pressure to obtain the title compound. This was purified by preparative liquid chromatography eluding with a 5:95 mixture of ethyl acetate and hexane to obtain 44.6 g (24 percent of theory) of material having a proton nmr spectrum consistent with the assigned structure.

The synthetic route of 38603-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4979978; (1990); A;,
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Application of 5307-02-8, These common heterocyclic compound, 5307-02-8, name is 2-Methoxybenzene-1,4-diamine, 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.

2.00 g (1 1.9 mmol) 2-chloro-l,3-dimethyl-4,5-dihydro-lH-imidazoL3-ium chloride (II) in 20 mL acetonitrile were added to a suspension of 0.66 g (4.7 mmol) 2-methoxybenzene-l ,4- diamine in 20 mL acetonitrile and 2.4 mL triethylamine under argon atmosphere. The mixture was stirred for 50 hours at room temperature. After filtration of the precipitate and distillation of the solvent, the residue was suspended in 2 M aqueous sodium hydroxide solution and stirred for 5 minutes at 45 C. The precipitate was filtered, the solvent distilled off, the residue suspended in acetonitrile/methanol mixture and filtered through an alumina pad (Polygram Alox N/UV254). 1.2 g (3.63 mmol; 77 %) orange solid were obtained after drying in vacuo. The product was purified by gradient sublimation for analytical characterisation. (0097) Melting point: 149 C

The synthetic route of 5307-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVALED GMBH; DOROK, Sascha; (34 pag.)WO2016/1425; (2016); A2;,
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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. 27841-33-4, name is 4,5-Dimethoxybenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4,5-Dimethoxybenzene-1,2-diamine

Step (a) Preparation of: 6,7-Dimethoxy-3-(2-pyridyl)-2-quinoxalinol A solution of ethyl 2-pyridylglyoxylate oxime (3.35 g) and 4,5-dimethoxyphenylenediamine (3.05 g) in 35% sulfuric acid (75 mL) was stirred at 75 C. for 17 hours. The solid, which formed on heating, was removed by filtration and dissolved in water. The solution was adjusted to pH 8 with concentrated NH4OH. The precipitate removed by filtration and washed with water. This solid was recrystallized from ethanol to give the product as a light brown solid (3.64 g).

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 27841-33-4.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US6548499; (2003); B1;,
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Synthetic Route of 633335-94-1, 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. 633335-94-1 name is 1-Fluoro-2-methoxy-4-vinylbenzene, 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.

To a solution crude C-16 (110 g, 723.39 mmol) in 39 ethanol (1000 mL) was added 10% 108 Pd/C (50 g). A balloon of hydrogen gas was mounted and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred under a hydrogen atmosphere overnight at room temperature. After stirring at RT overnight, the reaction was complete. It was filtered through a pad of Celite and concentrated in vacuo to provide crude compound, which was purified through column chromatography (100-200) silica gel, eluted using 3-5% 47 ethyl acetate/hexane to obtain the desired product C-15 as colorless liquid (24 g, 48% over the 2 steps).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Fluoro-2-methoxy-4-vinylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); 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. 870563-60-3, name is (4-Fluoro-2-methoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of (4-Fluoro-2-methoxyphenyl)methanamine

To a solution of 2-furaldehyde (41 muL, 0.5 mmol) in methanol (1.5 mL ) 4-fluoro-2- methoxybenzylamine (86 mg, 0.55 mmol), 2,6-dimethylphenyl isocyanide (72 mg, 0.55 mmol) and 2-butynoic acid (46 mg, 0.55 mmol) were added sequentially. The reaction mixture was stirred overnight. The volatiles were removed in vacuum and the residue was dissolved in dioxane (3 mL). Ytterbium trifluoromethanesulphonate (62 mg, 0.1 mmol) was added and the solution was heated at 1000C by microwave irradiation for 15 min. The mixture was cooled down to ambient temperature, filtered, and purified using preparative HPLC. The fractions containing the target compound were combined and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, and concentrated in vacuum to yiled the titled compound as yellowish solid (74 mg, 33%). IH NMR (400 MHz, CDCl3) delta ppm 7.43 (s, 1 H), 7.18 – 7.23 (m, 1 H), 7.02 – 7.11 (m, 3 H), 6.53 – 6.61 (m, 2 H), 6.45 – 6.50 (m, 1 H), 6.23 – 6.26 (m, 1 H), 5.95 (s, 1 H), 4.85 – 4.98 (m, 2 H), 3.75 (s, 3 H), 2.17 (s, 6 H), 1.96 (s, 3 H) MS (ESI) m/z 449 [M+H], MS (ESI) m/z 447 [M-H]

The synthetic route of 870563-60-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/8020; (2008); A1;,
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These common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, 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. Quality Control of (4-Ethoxyphenyl)methanamine

General procedure: A solution of carboxylic acid (0.5 mmol) and HATU (0.55 mmol)in anhydrous DMF (2 mL) was stirred at ambient temperature for10 min. To this solution, DIPEA (0.6 mmol) and correspondingamine (0.54 mmol) were added successively and the mixture wasstirred for 18 h. After concentration under reduced pressure, thereaction mixture was treated with water (5 mL) and extracted withDCM (2 5 mL). After evaporation of the solvent, the residue wascrystallized from an appropriate solvent or subjected to columnchromatography on silica gel (DCM/MeOH) or preparative HPLC

The synthetic route of (4-Ethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krasavin, Mikhail; Gureyev, Maxim A.; Dar’in, Dmitry; Bakulina, Olga; Chizhova, Maria; Lepikhina, Anastasia; Novikova, Daria; Grigoreva, Tatyana; Ivanov, Gleb; Zhumagalieva, Aisulu; Garabadzhiu, Alexander V.; Tribulovich, Vyacheslav G.; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2651 – 2673;,
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121588-79-2, name is trans-4-Methoxycyclohexanamine, belongs to ethers-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. Computed Properties of C7H15NO

Example 625: (2R)-2-[6-(5-chloro-2-{[trans-4-methoxycyclohexyl]amino}pyrimidin-4-yl)-1 – oxo-2,3-dihydro-1 H-isoindol-2-y l]-N-[(1 S)-2-hydroxy-1 -(3- methoxyphenyl)ethyl]propanamide (3479) (3480) A mixture of (R)-2-(6-(2,5-dichloropyrimidin-4-yl)-1-oxoisoindolin-2-yl)-N-((S)-2-hydroxy-1-(3- methoxyphenyl)ethyl)propanamide (Preparation 352, 0.1 g, 0.199 mmol), DIPEA (0.070 ml, 0.399 mmol) and trans 4-methoxycyclohexanamine (0.039 g, 0.299 mmol) (0.024 ml, 0.232 mmol) in 1 :1 EtOH:dioxane (1 mL) was heated at 80C under nitrogen overnight. The mixture was allowed to cool to room temperature and was concentrated under vacuum. The residue was dissolved in EtOAc and transferred into a separating funnel. 1 N HCI was added and the crude product was extracted with EtOAc. The combined organic extracts were washed with NaHC03, brine, dried (MgS04) and absorbed on silica. The crude product was purified by chromatography on the Companion (12 g column, 0- 5 % MeOH in DCM) to afford the title compound (0.06g, 050.1 %) as a white solid after trituration and evaporation from Et.20. 1 H NMR (DMSO-d6) delta: 8.56 (d, 1 H), 8.44 (s (br), 1 H), 8.07 – 8.01 (m, 1 H), 7.97 (d, 1 H), 7.75 (d, 1 H), 7.52 (s (br), 1 H), 7.28 – 7.19 (m, 1 H), 6.93 – 6.85 (m, 2H), 6.83 – 6.76 (m, 1 H), 5.06 – 4.96 (m, 1 H), 4.89 (t, 1 H), 4.85 – 4.80 (m, 1 H), 4.77 (d, 1 H), 4.60 (d, 1 H), 3.75 (s, 3H), 3.73 – 3.63 (m, 1 H), 3.57 – 3.52 (m, 2H), 3.23 (s, 3H), 3.16 – 3.06 (m, 1 H), 2.05 – 1.91 (m, 4H), 1.45 (d, 3H), 1.39 – 1.13 (m, 4H). LCMS: [M+H]+ = 594. Prepared using an analogous procedure to Example 625, from the appropriate (3482) dichloropyrimidine

The synthetic route of 121588-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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Synthetic Route of 3469-08-7, 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. 3469-08-7, name is 6-Methoxy-1H-indene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4 (1.00 g; 6.84 mmol; 1.00 eq.) in 50 ml of 3:1 tetrahydrofuran (37.50 ml) water (12.50 ml) and 1,3-dibromo-5,5-dimethylhydantoin (0.98 g; 3.42 mmol; 0.50 eq.) was stirred at room temperature for 30 min. Most of the THF was removed by rotaevaporation, and the product was extracted into ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and the solvent was removed under reduced pressure to yield a brown oil, which was dissolved in diethyl ether but no precipitation formed:The crude product was purified by Sepacore chromatography with DCM as eluent. 850 mg of 5 were obtained as a white solid.

The synthetic route of 6-Methoxy-1H-indene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; Abbott GmbH & Co. KG; US2012/40948; (2012); A1;,
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