Month: March 2021

Electric Literature of 13940-96-0, These common heterocyclic compound, 13940-96-0, name is 4-Phenoxybenzene-1,2-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.

For preparing the 3,4-diamino-diphenyl ether used as starting material, 172.5 g of 5-chloro-2-nitro-aniline were heated for 4 hours under reflux in 500 ml of dimethylformamide with 94 g of phenol in the presence of 150 g of anhydrous potassium carbonate. After cooling, the reaction mixture was diluted with 1000 ml of water, the 3-amino-4-nitro-diphenyl ether that had precipitated was filtered off with suction and purified by recrystallization from isopropanol. Yield: 110 g; melting point: 142C. 103 g Of the 3-amino-4-nitro-diphenyl ether so obtained were hydrogenated in 800 ml of dimethylformamide with Raney nickel under a pressure of 100 atmospheres gauge at room temperature, the catalyst was then removed by filtration and the solution was evaporated under reduced pressure. The 3,4-diamino-diphenyl ether that had formed was obtained in the form of a sirupy mass which was dissolved in ethanol and used in the reaction as described above.

The synthetic route of 13940-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US3954791; (1976); A;,
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Electric Literature of 37466-89-0, 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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Methoxybenzene-1,2-diamine dihydrochloride (Example 54(a)) was partitioned between 10% aq. Na2CO3 and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2¡Á). The combined organic extracts were dried over Na2SO4, filtered and evaporated to yield 3-methoxybenzene-1,2-diamine. A mixture of the diamine (912 mg, 6.6 mmol) and diethyl oxalate (9.0 mL, 66 mmol, Aldrich) was heated at 185 C. for 18 h. The reaction mixture was left to reach room temperature and the solid precipitate was filtered. The filter cake was washed with EtOH and dried in vacuo to give the title compound. MS (ESI, pos. ion.) m/z: 191 (M+1).

The synthetic route of 3-Methoxybenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Hui-Ling; Balan, Chenera; Doherty, Elizabeth M.; Falsey, James R.; Gore, Vijay Keshav; Katon, Jodie; Norman, Mark H.; US2005/176726; (2005); A1;,
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20265-97-8, name is 4-Methoxyaniline hydrochloride, 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. category: ethers-buliding-blocks

General procedure: A cold solution of aryldiazonium salt (2.0 mmol) was preparedby adding a solution of NaNO2 (2.2 mmol, 0.15 g into 1.0 mL H2O) toa cold solution of arylamine hydrochloride (2.0 mmol of arylaminein 1.5 mL conc. HCl). The resulting solution of aryl diazonium saltwas added drop wise to a mixture of compound (II) (2.0 mmol,0.43 g) in water (15 mL) containing NaOH (25 mmol, 1.0 g) at0e5 C. The pH of the reaction mixture was maintained at 9e10 byadding 2.5% sodium hydroxide solution. Then, the reaction mixturewas stirred for 2 h at the same temperature and the precipitate wasfiltered off and the resulting solid was washed with cold ethanoland dried at 50 C in an oven. The crude product was purified usingthe recrystallization method as mentioned in Table 1. Under thesame reaction conditions, a series substituted arylazo quinolonedyes were obtained in satisfactory yields (Table 1, Scheme 2).

The synthetic route of 20265-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rufchahi, E.O. Moradi; Gilani, A. Ghanadzadeh; Taghvaei; Karimi; Ramezanzade; Journal of Molecular Structure; vol. 1108; (2016); p. 623 – 630;,
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These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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. HPLC of Formula: C8H8Br2O

A mixture of B32.1 (4.3 g, 25mmol), CH3SNa (6.12 g, 4Smmol) in DMF (50 mL) was heated at 90 C for 18 h. DCM (50 mL) and water (100 mL) was added. The organic phase was separated andconcentrated to give the title compound (2.9 g, 80%). The crude product was used in the next step without further purification.

The synthetic route of 1-Bromo-4-(2-bromoethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (148 pag.)WO2017/221100; (2017); A1;,
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Application of 1978-39-8,Some common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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.

A solution of sodium nitrite (36 g, 0.51 mole) in water (50 mL) was slowly added to a solution of 5-fluoro-2-methoxy-phenylamine (61.5 g, 0.48 mol) in hydrochloric acid (20 % aqueous solution, 115 mL) at 0 C. After stirring for 10 minutes, a cooled (0 C) solution of acrolein (50 mL, 0.75 mol) in acetone (100 mL) containing calcium oxide (0.56 g, 0.010 mol) was added slowly to the reaction mixture. This was then followed by a solution of cuprous chloride (5 g, 0.05 mol) in acetone (100 mL) containing hydrochloric acid (20 % aqueous solution, 10 mL). The mixture was stirred at 0 to 30 C for 3 hours, and then extracted three times with dichloromethane (300 mL). The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give a black viscous oil. The crude product was passed through a short silica column to give the crude product, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Fluoro-2-methoxyaniline, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CLEVELAND, Thomas; MAKINGS, Lewis R.; HAMILTON, Matthew; GROOTENHUIS, Peter D.J.; WO2005/26137; (2005); A2;,
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Application of 1758-46-9, A common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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.

Intermediate 73: (6-BROMO-PYRIDIN-3-YLMETHYL)- (2-PHENOXV-ETHYL)-AMINE A solution of 2-bromo-pyridine-5-carbaldehyde (500MG, 2. 69MMOL) and 2- (PHENOXY)- ethylamine (594mg, 4.3mmol) in anhydrous ethanol (14ML) was stirred at room temperature for 7 hours. Sodium borohydride (102mg, 2. 7MMOL) was then added to the solution, and the resultant mixture was allowed to stir for a further 3 hours before being quenched with water. The resultant mixture was concentrated, to provide (6-BROMO- pyridin-3-ylmethyl)- (2-phenoxv-ethvl)-amine (quantitative), which was’used without further purification. LCMS (Method B): RT = 1. 79 minutes; 307 309 (M+H) +.

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; ARGENTA DISCOVERY LIMITED; WO2005/14588; (2005); A1;,
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Reference of 710-18-9, 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 710-18-9 as follows.

General procedure: Lewis acid (1.0-1.5eq) (powdered AlCl3, powdered FeCl3, 1 or 2 M solution of TiCl4 in CH2Cl2) was added portionwise to a stirred 1 M solution of the aromatic compound in dry CH2Cl2, and then 2a-f (1.2-1.5 eq) was added dropwise at 0C over a period of 2-10 min. The mixture was stirred for several hours at room temperature. Following complete conversion of starting material, as confirmed by GC analysis, the mixture was quenched with H2O and extracted with CH2Cl2 or EtOAc. The combined organic layers were successively washed with satd. aq. NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by distillation or column chromatography on silica-gel, if necessary.

According to the analysis of related databases, 710-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Warashina, Takuya; Matsuura, Daisuke; Kimura, Yoshikazu; Chemical and Pharmaceutical Bulletin; vol. 67; 6; (2019); p. 587 – 593;,
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Application of 450-91-9, These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-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.

To a mixture of 4-fluoro-2-methoxyaniline (25.0 g, 177 mmol), K2C03 (36.7 g, 266 mmol) and Nal (10.6 g, 0.07 mmol) in /- PrOH (250 ml.) was added bis(2-chloroethyl)amine hydrochloride (47 g, 177 mmol). The reaction mixture was refluxed overnight. The solvent was removed and the residue was purified by column chromatography (petroleum ether/EtOAc = 10:1 ) to provide 1 -(4-fluoro-2-methoxyphenyl)piperazine. MS: m/z 212.36 [M+H] +.

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
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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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., SDS of cas: 41789-95-1

General procedure: A mixture of Pd(OAc)2 (6.7 mg, 0.030 mmol, 10 mmol%), Cu(OAc)2 (54.45 mg, 0.30 mmol, 1 equiv.), 1a (32.1 mg, 0.30 mmol, 1equiv.), CsF (136.7 mg, 0.90 mmol, 3 equiv.) was dissolved in a solvent of acetonitrile (3 mL) followed by addition of 2a (179 mg,0.60 mmol, 2 equiv.). The reaction mixture was stirred at 120 C for 24 h and progress of the reaction was monitored continuously byTLC with ethyl acetate: hexane eluent system. Upon completion of reaction the mixture was cooled to room temperature, poured into brine, and extracted with EtOAc. The combined extracts were dried over MgSO4 and filtered through pad of Celite eluting with ethylacetate. The filtrate was concentrated under reduced pressure and was purified by column chromatography (EtOAc/hexane) on silicagel to afford the 5,6-dihydrophenanthridine 3a. Compound 1i was synthesized in accordance with reported literature [25]. Characterization data of compounds 3a, 3c, and 3e were found exactly similar as reported in the literature (References of above compounds are mentioned in Supplementary data).

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; Asamdi, Manjoorahmed; Chauhan, Prakashsingh M.; Patel, Janki J.; Chikhalia, Kishor H.; Tetrahedron; vol. 75; 25; (2019); p. 3485 – 3494;,
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These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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. Formula: C11H15BrO2

Step 1: Preparation of 3-(3-aminooxetan-3-yl)benzaldehyde Hydrochloride 3-Bromobenzaldehyde diethyl acetal (11.65 g, 45 mmol) in dry THF (100 mL) at -78 C. was added n-butyl lithium (2.5 M in hexanes, 19 mL, 47 mmol) dropwise. The sample was stirred at -78 C. for ten minutes then added 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfonamide (7.5 g, 43 mmol) dropwise. The sample was stirred at -78 C. for one hour. The mixture was diluted with 200 mL saturated ammonium chloride solution and 200 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude mixture was dissolved in ethyl acetate (250 mL). The reaction mixture was cooled to 0 C. was added 1M hydrochloric acid in ethyl acetate dropwise (24 mL, 24 mmol). The reaction mixture was stirred at 0 C. for one hour then vacuum filtered to give the desired product as a slightly off white solid (1.97 g, 9.2 mmol). 1H NMR (400 MHz, DMSO-d6) delta 10.08 (s, 1H), 9.18 (s, 3H), 8.09 (s, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.79-7.73 (m, 1H), 5.03-4.91 (m, 4H).

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

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
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