Tag: M.W=100-200

Electric Literature of 1758-46-9, 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. 1758-46-9, name is 2-Phenoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

d) (4-Methyl-7-trifluoromethyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine 4-Methyl-2-methylsulfanyl-7-trifluoromethyl-3,4-dihydro-quinazoline hydroiodide (116 mg, 0.30 mmol) and 2-phenoxyethyl amine (126 mg, 0.9 mmol) were dissolved in acetonitrile (0.9 ml) and heated to 170° C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution, methylene chloride and 5 to 7 drops of 30percent aqueous hydrogen peroxide solution. After the reaction has ceased the reaction was diluted with little water and the precipitated product was filtered off, washed with water, dried in vacuo to yield the title compound as a white solid (104 mg, 94percent). (MS: m/e=350.2, 351.1 [M+H+]). 1H NMR (CDCl3): delta 1.25 (3H, d), 3.58 (2H, m), 4.05 (2H, t), 4.55 (1H, q), 6.08 (1H, bt), 6.37 (1H, s), 6.91-7.01 (5H, m), 7.11 (1H, d), 7.29 (2H, t).

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

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
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Synthetic Route of 1116-77-4, 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. 1116-77-4, name is 4,4-Diethoxy-N,N-dimethyl-1-butanamine, This compound has unique chemical properties. The synthetic route is as follows.

Example 9 (0448) Synthesis of N-(4-(2-acetoxy-4-methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan- 1 -aminium bromide (0449) In a N2 purged 20mL weighed glass vial with stir bar is added 1 .5g (0.004mol, 1 .0 eq) of AcO-Bzp-OMe-CH2-Br prepared in Example 7 and 8 mL ethyl acetate to give a clear solution on stirring for 20mins at RT. 2.06 g 4,4-Diethoxy-N,N-dimethyl-1 -butanamine (0450) (NNDMABADEA, from TCI-America) (0.01 mol, 2.5 eq) is slowly added to the reaction solution with stirring. A precipitate is soon formed and gradually thickenes with stirring over 30- 60minutes. The reaction mixture is stirred at RT overnight. The stirring is stopped and the mixture is allowed to stand for an hour. The mixture is filtered through a coarse filter frit at around 850mbar. The precipitate is washed five times with 10ml_ ethyl acetate. The precipitate is transferred into a 10OmL rb flask with about 18ml of Dl Water. The residual organics are removed under reduced pressure to give a clear solution. The solution is filtered through a Whatman1 (1 1 urn) filter paper to give a clear solution with neutral pH, that is frozen and lyophilized to give a off white solid which is confirmed to be N-(4-(2-acetoxy-4- methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan-1 -aminium bromide and is stored under dry N2 in desiccator.

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

Reference:
Patent; NOVARTIS AG; CHANG, Frank; DESOUSA, Ryan; HOLLAND, Troy Vernon; LAREDO, Walter R.; (68 pag.)WO2017/93835; (2017); A1;,
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Related Products of 171290-52-1, These common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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 solution of methoxy ethynylbenzenes (20 mmol) and methoxy substituted aryl iodide (22 mmol) in isopropylamine (120 ml) were added Pd(PPH3)2Cl2 (0.2 mmol) and CuI (0.4 mmol). The reaction mixture was stirred at ambient temperature for 6 hours under a slow stream of nitrogen. The reaction mixture was filtered and the residues were washed with ethyl acetate and the solvent evaporated from the combined filtrates. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (9:1) as an eluent to give methoxytolans.

Statistics shows that 3,5-Dimethoxyphenylacetylene is playing an increasingly important role. we look forward to future research findings about 171290-52-1.

Reference:
Patent; KENT STATE UNIVERSITY; SUMMA HEALTH SYSTEM; WO2008/157745; (2008); A1;,
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Reference of 54149-17-6,Some common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11BrO2, 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.

3-(2-(2-Methoxyethoxy)ethoxy)prop-1-yne (9) To a stirred suspension of sodium hydride (3.12 g, 78.0 mmol) in THF (100 mL) cooled to 5 C. in an ice-bath was added a solution of propargyl alcohol (4.60 g, 78.0 mmol) in THF (20 mL) drop-wise. The mixture was stirred at 5 C. for 30 min and was then allowed to warm to RT and treated dropwise with 1-bromo-2-(2-methoxyethoxy)ethane (7.00 mL, 52.0 mmol). The reaction mixture was stirred at RT for 16 hr and was then, diluted with water (100 mL) and extracted with diethyl ether (2*100 mL). The combined organic extracts were dried, filtered and evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 30% EtOAc in heptane, to afford the title compound (9) (250 mg, 9%) as a colourless oil: 1H NMR (500 MHz, MeOD) delta: 4.18 (2H, d), 3.66-3.69 (2H, m), 3.60-3.66 (4H, m), 3.52-3.56 (2H, m), 3.36 (3H, s), 2.84 (1H, t).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-(2-methoxyethoxy)ethane, its application will become more common.

Reference:
Patent; King-Underwood, John; Ito, Kazuhlro; Murray, Peter John; Hardy, George; Brookfield, Frederick Arthur; Brown, Christopher John; US2012/208799; (2012); A1;,
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Application of 801282-00-8, These common heterocyclic compound, 801282-00-8, name is 2-Fluoro-3-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.

[00385] Intermediate 30. l-(3-Chloro-2-fluorophenyl)-5-methoxy-lH-l,2,3-triazole-4- carboxylic acid: To a solution of 2-fluoro-3-methoxyaniline (1 g, 7.09 mmol) in TFA (10 mL) and water (5 mL) at 0 C was added an aq. solution of NaN02 (0.733 g, 10.63 mmol) dropwise. The resulting mixture was stirred at 0 C for 0.5 h and NaN3 (0.921 g, 14.17 mmol) was added portionwise. The reaction mixture was gradually warmed to rt and stirred for 4 h. The reaction was quenched with water (150 mL) and extracted with EtOAc (2×100 mL). The organic layer was washed with sodium phosphate solution (10%) and brine (50 mL), dried, and concentrated. The resulting brown oil was re- dissolved in DMSO (20 mL) and added t-butylpropiolate (1 mL) followed by K2CO3 (1 g), Cu(OAc)2 (0.2 g), and sodium ascorbate (100 mg). The resulting mixture was stirred at rt overnight. The reaction was quenched with water (200 mL) and extracted with EtOAc (2 x 100 mL). The organic layer was dried and concentrated. The residue was purified by silica gel chromatography to yield the desired product as brown oil. 1H NMR (400 MHz, CDCI3) delta 13.19 (br. s., 1H), 7.36 – 7.20 (m, 2H), 7.17 – 6.95 (m, 1H), 6.76 (td, J = 8.1, 1.3 Hz, 1H), 3.91 (s, 3H), 1.74 – 1.49 (m, 10H). MS(ESI) m/z: 238.0 (M+H)+.

The synthetic route of 801282-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); 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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, A new synthetic method of this compound is introduced below., Quality Control of 2-(Benzyloxy)-1-ethanamine

Example 25; 5-cvclopropyl-2-(4-fluorophenyl)-6-(N-((2-hvdroxy-1 ,2-oxaborolan-4- yl)methyl)methylsulfonamido)-N-(2-hvdroxyethyl)benzofuran-3-carboxamideStep 1: N-(2-(benzyloxy)ethyl)-5-cyclopropyl-2-(4-fluorophenyl)-6- (methylsulfonamido)benzofuran-3-carboxamide5-Cyclopropyl-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (1 .0 g, 2.568 mmol) was stirred in dry DMF (15 mL) at ambient temperature with DIPEA (0.730 g, 5.650 mmol) and HATU (1.71 g, 3.082 mmol). After stirring for 15 minutes, benzyloxymethanamine (1 .552 mg, 10.272 mmol) in 15 mL of THF was added. The reaction mixture was stirred for another 2 hours and diluted with EtOAc (30 mL) and water (30 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (30 mL x2). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by columnchromatography (eluting with 0-50% ethyl acetate in petroleum) to give N-(2- (benzyloxy)ethyl)-5-cyclopropyl-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3- carboxamide (1.4 g, crude, 104% yield).

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; GLAXO GROUP LIMITED; JOHNS, Brian Alvin; SHOTWELL, John Brad; HAIGH, David; WO2012/67663; (2012); A1;,
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Reference of 2930-05-4, 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. 2930-05-4 name is 2-((Benzyloxy)methyl)oxirane, 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.

In a glass RBF equipped with a Teflon- coated magnetic stirrer and a reflux condenser was dissolved 2-benzyloxymethyl-oxirane (1 eq.) in a 3:1 (v/v) solution (0.08 M) of methanol and water. To this was then added sodium azide (2 eq.) and ammonium chloride (1.5 eq.), and the resulting mixture was heated at reflux for 14 h. The reaction solution was cooled to RT and diluted with tBuOMe. The organic layer was separated, washed further with sat. aq. NH4C1, dried over MgSO4, and filtered. Concentration of the filtrate in vacuo delivered the crude product as a pale yellow oil. Further purification by way of column chromatography (Si02, gradient elution, 9:1 (v/v) Hex: EtOAc – 3:7 (v/v) Hex:EtOAc) furnished the desired product as a colorless oil (71% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-((Benzyloxy)methyl)oxirane, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (2017); 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Methoxyphenoxy)ethylamine

2-(2-Methoxyphenoxy)ethyl amine (15.09 g), N,N-diisopropylethyl amine (10.8 g), 4-(oxiran-2yl-methoxy)-9H-carbazole (20.0 g) and monoglyme (30 mL) were heated to 80-850C. After 8-12 hours, the reaction mixture was cooled to room temperature and ethyl acetate (40 mL) was added. The contents were cooled to 0-50C. The solid is filtered after slurry in ethylacetate to get crude Carvedilol (100 mL). (Purity: 98.62%; Yield: 36.26 %; Bis-impurity: 0.65%.)

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INOGENT LABORATORIES PRIVATE LIMITED1; WO2009/157015; (2009); A2;,
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Some common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, 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. HPLC of Formula: C8H11NO

4-Methoxybenzylamine (600 g, 4.37 mol) and 4-methoxybenzaldehyde (532 mL, 4.37 mol) were added to a 10 L RBF at ambient temperature. An exotherm was observed and a white precipitate formed. The mixture was stirred for 1 h and then anhydrous EtOH (4.8 L) was added. After an additional 15-3 0 mm at RT, sodium borohydride granules (99 g, 2.62 mol) were added portionwise over 2 h (during the addition of the NaBH4, the internal temperature of the reaction rose to 42 C), and the mixture was further stirred at RT overnight. The reaction was then quenched slowly with water (600 mL) and then was concentrated in vacuo. The residue was partitioned between water (4 L) and DCM (4 L), and the aqueous layer was extracted with more DCM (2 x 2 L). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide 361.01 (1112 g, 99% yield) as a semi-solid. The material was used directly in the next step without futher purification. 1H-NMR (400 MHz, CDC13) oe 7.28 (t, J=7. 1 Hz, 4H), 6.89 (d, J=8.6 Hz, 4H), 3.83 (m, 6H), 3.76 (s, 4H). LCMS-ESI (pos.) m/z: 258.4 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2393-23-9, its application will become more common.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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Application of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

N-(3-Benzyloxy-phenyl)guanidine: To a suspension of 3-benzyloxyphenylamine (20.0 g, 100.35 mmol) in 1,4-dioxane (150 mL) was added cyanamide (7.39 g, 175.95 mmol) followed by 4M HCl in 1,4-dioxane (44 ml, 176.00 mmol). The resulting suspension was heated at 80° C. overnight then cooled to ambient temperature and 6N NaOH (35 ml, 210.00 mmol) was added. The volume of solution was reduced to 50 ml in vacuo and the resulting precipitate was collected by filtration. The solid product was dried under vacuum overnight to afford23.8 g in 98.4percent yield. 1H NMR (MeOH-d4) delta 6.4-7.5 (m, 9H), 5.1 (s, 2H)

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

Reference:
Patent; Cao, Jingrong; Green, Jeremy; Moon, Young-Choon; Wang, Jian; Ledeboer, Mark; Harrington, Edmund; Gao, Huai; US2003/96816; (2003); A1;,
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