Month: May 2021

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. 33839-11-1, name is 4-Bromo-2-ethyl-1-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromo-2-ethyl-1-methoxybenzene

A mixture of bromide (1.3g, 6. 02MMOL, from step 1), 1-CYCLOPENTYL-2-PROPEN-1-OL (1.14g, 9. 07mmot), DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (LL) (85 mg, 0 12 mmol), sodium bicarbonate (0.61 g, 7.25 MMOT) in N-METHYLPYRROLIDINONE (12mL) was heated to 140 C under N2 for 5h. The reaction mixture was partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated’to a brown oil. The oil was purifed by silica gel chromatography to give the title compound as a yellow oil (0.74g, 47%). 1H NMR (CDCL3): No. ?1. 17 (t, 3H, J = 7.6 Hz), 1. 54-1. 80 (M, 9H), 1.17 (q, 2H, J= 7. 6 HZJ,-2. 73 (m, 2H), 2.84 (m, 2H), 3.80 (s, 3H), 6.75 (d, 1H, J= 8. 0Hz), 6.97 (m, 2H).

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 33839-11-1.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
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Reference of 202865-58-5, 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. 202865-58-5 name is 1-Bromo-4,5-difluoro-2-methoxybenzene, 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.

Add trifluoromethanesulfonic acid 6-methoxy-1- [4- (2-piperidin-1-yl-ethoxy)- benzoyl] -naphthalen-2-yl ester (2.3 gm, 4.2 mmoles), bis (pinacolato) diboron (1.3 gm, 5.1 mmoles), palladium II acetate (97 mg, 0. 4 mmoles), triphenylphosphine (222 mg, 0.84 mmoles) and cesium fluoride (2.1 gm, 14.1 mmoles) in a 250 ml round bottom flask under nitrogen and add 100 ml of anhydrous acetonitrile. Stir and heat to reflux for 2 hours. Allow the mixture to cool and to this mixture add 2-bromo-4,5-difluoroanisole (2.8 gm, 12.5 mmoles), palladium II acetate (96 mg, 0.43 mmoles) triphenylphosphine (222 mg, 0.84 moles) and cesium fluoride (1.8 gm, 12.2 mmoles). Reflux the mixture for 18 hours and filter through Celite. Evaporate the solvent and pass through an SCX column eluting the product with 2N ammonia/methanol. The product is purified on a silica column eluting with a gradient of 25% THF/hexane to 5% 2N ammonia/methanol in 25 % THF/Hexane. LC/MS gives a peak with the proper mass.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4,5-difluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 53903-49-4, name is 4-Methoxy-2-(trifluoromethyl)aniline, 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 53903-49-4, Quality Control of 4-Methoxy-2-(trifluoromethyl)aniline

Dissolve 4-methoxy-2-(trifluoromethyl)aniline (4.8 g, 25.1 mmol) in dichloromethane (10 mL),Triethylamine (5.0 g, 50.0 mmol) was addedAnd acetic anhydride (5.0 g, 50.0 mmol).The reaction solution was stirred at room temperature overnight.After the reaction was completed, water (100 mL) was added.Extract with dichloromethane (100 mL x 3).Combine the organic phase,The organic phase was washed with saturated brine (100 mL).Drying with anhydrous sodium sulfateConcentration under reduced pressure gave a grey solid.The gray solid was washed with a mixture of petroleum ether and ethyl acetate (20:1).A white solid was obtained (5.4 g, yield: 92.3%).

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; Tianjin Binjiang Pharmaceutical Research And Development Co., Ltd.; Tian Hongqi; Huang Gongchao; Cheng Ying; (48 pag.)CN107793413; (2018); A;,
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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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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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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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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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
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. 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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem