Tag: M.W=100-200

1484-26-0, name is 3-Benzyloxyaniline, 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. Product Details of 1484-26-0

Phenyl [3-(benzyloxy)phenyl]carbamate; To a stirred solution of 3-benzyloxyaniline (0.999 g, 5.01 mmol) in DCM (10 piL) was added pyridine (1.22 ml, 15.03 mmol) and phenyl chloroformate (0.68 ml, 5.51 mmol) dropwise (Exotherm.). The reaction was then allowed to stir at room temperature for 2 hours. The reaction mixture was then partitioned between DCM and IM HCl, extracted twice, combined organics passed through phase separating cartridge and filtrate evaporated to dryness to give an orange solid. This was then triturated in 10percent ethyl acetate/ hexanes, filtered and dried to give the product, phenyl [3-(benzyloxy)phenyl]carbamate, as beige solid (1.209 g, 3.78 mmol, 75percent yield).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/67401; (2006); A1;,
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Application of 74654-07-2, A common heterocyclic compound, 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, molecular formula is C7H17NO3, 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.

5-Amino-3,5-dichloro-l,2,4-triazine (1.460 g, 8.85 mmol) was dissolved in dioxane (30 mL) at room temperature. Triethylamine (2.7 mL, 19.37 mmol) was added, followed by addition of mPEG3-NH2 (1.9812 g, 12.14 mmol). The resulting mixture was stirred at 95 C for 7 h. The mixture was cooled to room temperature, filtered to remove the white solid and the solid was washed with ethyl acetate. The combined organic solution was concentrated and purified with flash column chromatography on silica gel (1-10% methanol/dichloromethane) to afford 2.1236 g of product as solid. The yield was 82%. [0485] 1H-NMR (500 MHz, CDC13): 3.691-3.654 (m, 6H, 3CH2), 3.625-3.594 (m, 6H, 3CH2), 3.436 (s, 3H, CH3). LC-MS: 292.1 (MH+/z).

The synthetic route of 74654-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT. LTD.; NEKTAR THERAPEUTICS; SHARMA, PANKAJ; KHATRI, VIJAY KUMAR; GU, XUYUAN; SONG, YUAN; SHEN, MICHAEL LIXIN; SAUTHIER, JENNIFER RIGGS; ANAND, NEEL K.; KOZLOWSKI, ANTONI; ODINECS, ALEKSANDRS; RILEY, TIMOTHY A.; REN, ZHONGXU; MU. YONGQI; SHEN, XIAOMING; YUAN. XUEJUN; AURRECOECHEA, NATALIA; O’MAHONY, DONOGH JOHN ROGER; WO2015/92819; (2015); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1978-39-8, name is 5-Fluoro-2-methoxyaniline, 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 1978-39-8, Computed Properties of C7H8FNO

General procedure: A primary amine (17.8 mmol) was dissolved/suspended in acetonitriie (50 ml) and then heated to reflux temperature. Then 2,6-lutidine (20 ml, 173 mmol) was added. A solution of DMP3C-BF4 (5.04 g, 9.88 mmol) was dissolved in acetonitriie (250 ml) and then added slowly dropwise (1 drop per 5-10 s) to the hot solution of the phenol compound. The addition was allowed to proceed overnight (16 h). The red reaction mixture was analyzed by MALDI-TOF (dithranol matrix) and this analysis indicated that no starting material was present. The reaction mixture was allowed to cool down, and then poured into an acidified KPF6 solution (10 ml 2 M HCI in 1500 ml 0.2 M KPF6) upon vigorous stirring. A red precipitate formed and the suspension was gen-tly stirred for 15 min and then filtered . The filtrate was washed with HCI solution (2 M), then with water, and finally with heptane until the heptane phase was nearly colorless. The red sticky mass was dissolved in a minimum of CH2CI2 through the filter. The product was precipitated with heptane and filtered off and washed with heptane (2 x 100 ml). The product was dissolved in a minor amount of acetonitrile and poured onto diethyl ether upon stirring. The red precipitate was allowed to form for 15 min, filtered off, and then washed with ether (2 x 100 ml). The red sticky product was collected and dissolved in CH2CI2. The CH2CI2 was removed by evaporation yielding 17 g of red-gray fine powder. The red powder was suspended in pure water and stirred overnight. The red powder was filtered off, washed with water, and sucked dry. The sticky red product was dissolved in acetonitrile through the funnel and then the solvent was removed by evaporation. The red powder was collected and dried on an oil pump for 1 day.

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Reference:
Patent; KØBENHAVNS UNIVERSITET; LAURSEN, Bo V.; ROSENBERG, Martin; SØRENSEN, Thomas Just; WO2015/58777; (2015); A1;,
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16452-01-0, name is 3-Methoxy-4-methylaniline, 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. Safety of 3-Methoxy-4-methylaniline

Step A 4-Methyl-3-methoxyphenylhydrazine A stirred mixture of 100.0 g (0.73 mole) of 4-methyl-3-methoxyaniline in 800 mL of concentrated hydrochloric acid was cooled to -5 C. A solution of 501.5 g (0.73 mole) of sodium nitrite in 250 mL of water was added slowly while maintaining the temperature of the reaction mixture below 0 C. The resultant mixture was stirred at -5 C. for 30 minutes. A cold solution of 330.0 g (1.46 mole) of tin (II) chloride dihydrate in 360 mL of concentrated hydrochloric acid was added over one hour. After complete addition the resultant mixture was allowed to warm to room temperature. A solid precipitate formed and was collected by filtration and stirred in 200 mL of water. This mixture was neutralized with 50% aqueous sodium hydroxide, and extracted with toluene. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 58.0 g of 4-methyl-3-methoxyphenylhydrazine as an oil.

The synthetic route of 16452-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US4806145; (1989); A;,
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Application of 2752-17-2, 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. 2752-17-2, name is 2,2′-Oxydiethanamine, This compound has unique chemical properties. The synthetic route is as follows.

8-hydroxyjulolidine-9-carboxaldehyde0.91 g (4 mmol) was dissolved in 10 mL of ethanol,With two drops of hydrochloric acid2,2′-oxybis (ethylamine)0.22 mL (2 mmol) was slowly added to the solution. The mixture was stirred at room temperature for one day so that the mixed solution was well mixed. After the solvent was removed under reduced pressure, the crude product obtained was purified by column chromatography using a mixed solution of methylene chloride and methanol (MC: MeOH = 10: 1, v / v) to obtain 0.65 g of pure product. It was analyzed by 1 H-NMR, 13 C-NMR, ESI-MS, and EA to confirm that it had the structure of Formula 1, and the yield was 65%.

The chemical industry reduces the impact on the environment during synthesis 2,2′-Oxydiethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Seoul National University of Science and TechnologyIndustry-AcademicCooperation Foundation; Kim, Chul; Song, Uhn Ju; Lee, Myung Mi; (17 pag.)KR2016/34631; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 41406-00-2, name is 3-Isopropoxyaniline, 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 41406-00-2, Computed Properties of C9H13NO

Example 3; General Procedure for Synthesis of Second Purine SNAr Products; The mono-SNAr product 14 (40 mg, 0.12 mmol) and 3-isopropoxyaniline (44 mul, 0.3 mmol) were added to a microwave vial, followed by the addition of isopropyl alcohol (IPA, 0.8 mL) and 4 drops of TFA. The mixture was irradiated in a microwave oven at 155 C. for 60 minutes to effect the desired reaction. After cooling the reaction vessel to room temperature, the volatiles were evaporated under reduced pressure. The residue was purified by reverse-phase high performance liquid chromatography (RP-HPLC), eluting with a gradient of acetonitrile-water to provide the desired product 129, racemic-(2-exo,3-exo-)-N6-[3-(dimethylamino)carbonylbicyclo[2.2.1]hept-5-en-2-yl)]-N2-(3-isopropoxyphenyl)-1H-purine-2,6-diamine.

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Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; US2007/142402; (2007); A1;,
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Electric Literature of 150-78-7, 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. 150-78-7, name is 1,4-Dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 1-Methoxy-3,5-dimethylbenzene(100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reaction was monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetate and cooled at 0 C. The product was isolated as filtrate upon paper filtration and waste succinimide as precipitate. The resulting filtrate were concentrated in vacuo to isolate 250 mg (yield: 85%) of 2b as colourless powder. To test the efficiency in large scale, the reaction was also performed for the mono-bromination of 1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product was isolated in 87% yield.[1] The milling apparatus was stopped and small portion of the sample was collected from the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing.

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

Reference:
Article; Bose, Anima; Mal, Prasenjit; Tetrahedron Letters; vol. 55; 13; (2014); p. 2154 – 2156;,
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Synthetic Route of 592-55-2, 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. 592-55-2, name is 1-Bromo-2-ethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 15Production of Compound A-7In a 100 ml four-neck flask, 8.567 g (0.0400 mol) of 3-hydroxynaphthalic anhydride, 48.0 g of dimethyl sulfoxide, and 10.081 g (0.0730 mol) of potassium carbonate were put and stirred, and the atmosphere in the system was replaced with nitrogen gas. Dropwise added was 11.233 g (0.0734 mol) of bromoethyl ethyl ether, and the resultant was stirred at 70 C. for 5 hours. In the reaction liquid, 12 ml of deionized water and 9.6 ml of 48% by weight aqueous sodium hydroxide solution were put, stirred at 50 C. for 2 hours, and thereafter ice-cooled, and 21.0 g of 35% by weight aqueous hydrochloric acid solution was put and stirred at 60 C. for 2 hours. The reaction liquid, 500 ml of methylene chloride, and 200 ml of deionized water were added and subjected to oil-water separation to yield the organic layer, which was washed three times with 200 ml of deionized water and thereafter concentrated, and the organic layer was concentrated and subjected to purification by silica gel chromatogram (developing solvent with a hexane-to-ethyl acetate volume ratio of 2 (hexane):3 (ethyl acetate)) to yield the compound A-7 which was a target as a pale yellow solid. Yield: 5.20 g (yield: 45.4%), purity: 98.3% by HPLC (column: Inertsil ODS-2 manufactured by GL Sciences Inc., 4.6 mm×250 mm, solvent: acetonitrile/water=7/3, L-7455 diode array detector manufactured by Hitachi, Ltd., detection wavelength: 230 nm). The measurement results of 1H-NMR by a deuterated dimethyl sulfoxide solvent are listed in Table 1-3.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-ethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Murai, Toshihiko; Makabe, Yoshie; Fujita, Shohei; US2012/289697; (2012); A1;,
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171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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. Application In Synthesis of 3,5-Dimethoxyphenylacetylene

To a solution of 69 benzyl-3-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)azetidine-1-carboxylate 2e (0.123 g, 0.31 mmol), 43 1-ethynyl-3,5-dimethoxybenzene (0.740 g, 3.10 mmol) and 44 triethylamine (0.310 g, 3.10 mmol) in 32 N,N-dimethylformamide (5 mL), under nitrogen protection, were added 45 cuprous iodide (12 mg, 0.06 mmol) and 46 1,1?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (22 mg, 0.03 mmol). The mixture was heat to 80 C. and stirred for 5 h. The mixture was cooled to room temperature, quenched with saturated ammonium chloride solution (10 mL) and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with brine (20 mL×2), dried over anhydrous sodium sulfate and filtered. The residue was purified by preparative-TLC (19:1 dichloromethane/methanol) to provide 71 benzyl-3-(8-amino-1-((3,5-dimethoxyphenyl)ethynyl)imidazo [1,5-a]pyrazin-3-yl)azetidine-1-carboxylate2f (52.5 mg, 0.11 mmol, grey solid), yield: 35%.MS m/z (ESI): 484 [M+1].

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU INNOCARE PHARMA TECH CO., LTD.; KONG, Norman Xianglong; ZHOU, Chao; CHEN, Xiangyang; US2019/177333; (2019); A1;,
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Application of 2393-23-9, These common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, 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.

A mixture of l-[4-(methyloxy)phenyl]methanamine (40 g) and 4- (methyloxy)benzaldehyde (40.5 g) in methanol (220 mL) was heated to reflux for 3 hours. After cooling to 0 C, NaBH4 (14.34 g) was added portionwise within 30 min and the resulting mixture was stirred at room temperature overnight. Solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc for 3 times. The combined organic layers were washed with water and brine, then dried over anhydrous Na2SC>4. After filtration, solvent was removed in vacuo to afford bis {[4-(methyloxy)phenyl]methyl} amine (75.9 g) as a colorless oil. MS(ES+) m/z 258 (MH+).

Statistics shows that 4-Methoxybenzylamine is playing an increasingly important role. we look forward to future research findings about 2393-23-9.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; XIANG, Jia-Ning; WO2012/27965; (2012); A1;,
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