Month: August 2021

Reference of 710-18-9, A common heterocyclic compound, 710-18-9, name is 1-Methoxy-4-(trifluoromethoxy)benzene, molecular formula is C8H7F3O2, 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.

Under N2 atmosphere, an oven-dried 4 mL vial was charged with l-methoxy-4- (trifluoromethoxy)benzene (57.6 mg, 45.5 mu, 0.300 mmol, 1.00 equiv), palladium complex 1 (11.4 mg, 15.0 muetaiotaomicron, 5.00 mol ), Ag(bipy)2C104 (16.0 mg, 30.0 muetaiotaomicron, 10.0 mol ), and NFBS (0.189 g, 0.600 mmol, 2.00 equiv). Acetonitrile (0.75 mL, c = 0.40 M) was added and the reaction mixture was stirred in a sealed vial at 23 C for 24 h. Subsequently, triethylamine (30.5 mg, 42.0 mu, 0.300 mmol, 1.00 equiv) was added and the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with hexanes/EtOAc (19: 1 to 4: 1 (v/v) with 1% triethylamine), to afford 89.2 mg of the title compound as a colorless solid (61 yield). [00215] Rf = 0.30 (hexanes/EtOAc 4: 1 (v/v)). NMR Spectroscopy: 1H NMR (600 MHz, CDC13, 23 C, delta): 7.97 (d, J = 7.6 Hz, 4H), .65-1.69 (m, 2H), 7.54 (t, J = 7.6 Hz, 4H), 7.29 (dd, J = 9.5, 2.9 Hz, 1H), 6.95 (d, J = 2.9 Hz, 1H), 6.85 (d, J = 8.6 Hz, 1H), 3.43 (s, 3H). 13C NMR (125 MHz, CDC13, 23 C, delta): 156.8, 141.8, 139.8, 134.0, 128.9, 128.9, 126.5, 125.1, 123.4, 120.6 (q, J = 255 Hz), 112.4, 55.8. 19F NMR (375 MHz, CDC13, 23 C, delta): -59.9. Mass Spectrometry: HRMS (ESI-TOF) (m/z): calcd for C20H2oF3N206S2 [M + NH4]+, 505.0709, found, 505.0721.

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; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; NGAI, Ming-Yu; BOURSALIAN, Gregory, Bagrad; MCNEILL, Eric, Andrew; RITTER, Tobias; WO2015/31725; (2015); A1;,
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Electric Literature of 5111-65-9, These common heterocyclic compound, 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, 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.

6-Methoxy-2-bromonaphthalene (0.97 g, 4.1 mmol) was dissolved in 20 mL of dry THF, protected under nitrogen, (3.4 mL, 8.2 mmol) was added, stirred for 1 hour, and then anhydrous DMF (0.941 mL, 12.3 mmol) was added dropwise at -78 C,The reaction was continued at 78 C for 1 hour, rose to room temperature, acidified to pH = 5 with 2N hydrochloric acid, extracted with ethyl acetate, washed with water, saturated brine Washed with anhydrous sodium sulfate, filtered and concentrated, n-hexane / ethyl acetate (15: 1) column chromatography to isolate 6-methoxy-2-naphthyl Aldehyde, the yield of 88.6%.

Statistics shows that 2-Bromo-6-methoxynaphthalene is playing an increasingly important role. we look forward to future research findings about 5111-65-9.

Reference:
Patent; Liaocheng University; Liu Guoyun; Yang Jie; Li Xiaoteng; Guo Shangjing; (19 pag.)CN105111054; (2017); B;,
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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., SDS of cas: 1836-62-0

Example -4: Preparation of carvedilol In a dry reaction flask charged 25.0 g 4 – (2,3-epoxy propoxy) carbazole (0.104 moles), 39.35 g of 2 – (2- methoxy phenoxy) ethylamine (0.235moles) in 250 ml dimethyl sulfoxide. The temperature of the reaction mass was raised to about 70C under stirring and maintaining the reaction mixture at 68 – 72C for 18 – 20 hrs. The reaction mass was cooled to about 30C and quenched the reaction mass in 250 ml water, stirred and extracted the resultant solution in 250 ml dichloromethane. The organic layer was separated and washed with aqueous sulphuric acid till pH of the washings about 7.0 – 8.0. The organic layer was separated and further adjusted the pH with the aqueous sulfuric acid to 4.0 – 4.5 to precipitate carvedilol sulphate salt. The precipitated salt was filtered and taken in 300 ml ethyl acetate and made alkaline with 10% sodium carbonate solution. The reaction mass was stirred and separated the organic layer. The ethyl acetate was distilled under vacuum, and 330 ml toluene was added to it. The solid obtained was filtered and crystallized from ethyl acetate to obtain pure carvedilol. Yield = 58 – 62%.

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; IPCA Laboratories Limited; EP1741700; (2007); A1;,
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Synthetic Route 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.

General procedure: A solution of compound (ZDR019) (3.0 g, 7.88 mmol), dimethylamine hydrochloride (1.92 g, 23.6 mmol), sodium triacetoxyborohydride (3.32 g, 15.7 mmol) and N,N- diisopropylethylamine (4.8 ml_, 27.5 mmol) in 1,2-dichloroethane (150 mL) was stirred at room temperature for 18 h. The reaction was quenched through the addition of water (100 mL) and the pH adjusted to pH 6-7 using aqueous phosphate buffer solution (0.5 M, pH 7) . The mixture was then diluted with dichloromethane (100 mL) and the separated aqueous layer further extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with aqueous phosphate buffer solution (0.5 M, pH 7) (100 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash chromatography (dichloromethane/methanol, 20: 1 10: 1 7: 1) afforded compound (ZDR022) as a white solid (2.40 g, 5.86 mmol, 74%).

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

Reference:
Patent; OTAGO INNOVATION LIMITED; BRIMBLE, Margaret Anne; COOK, Greg Murray; FERGUSON, Scott Andrew; HEIKAL, Adam; RENNISON, David; (130 pag.)WO2019/125185; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10541-78-3, name is 2-Methoxy-N-methylaniline, 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 10541-78-3, HPLC of Formula: C8H11NO

To a stirring dichloromethane (40 mL) solution containing 5-bromo-4- chloro-2-hydroxybenzoic acid (2.0 g, 8.0 mmol), were added triethylamine (2.2 mL, 16.0 mmol), HATU (4.5 g, 12 mmol) and 2-methoxyl-N-methylaniline (1.19 g, 8.7 mmol). The mixture was stirred at rt for 16 hrs and water was added. The organic layer was separated, washed with NaHCO3, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with 20% ethyl acetate in hexane to afford 5-bromo-4-chloro-2-hydroxy-N-(2- methoxy-phenyl)-N-methyl-benzamide (300 mg). MS [M+H]+: 371.9; tR = 2.60 min (method 1)Alternatively, a mixture of 5-bromo-4-chloro-2-hydroxybenzoic acid (5 g, 19.9 mmol), 2-methoxy-N-methyaniline (3.13g, 22.9 mmol) and P2O5 (5.36g, 37. 8 mmol) in anhydrous xylene was heated at 60 0C for 2 hrs and then refluxed for 17 hrs. The mixture was concentrated and purified via silica gel flash column chromatography eluted with ethyl acetate in hexane (20%) to give 5-bromo-4-chloro-2-hydroxy-N-(2- methoxy-phenyl)-N-methyl-benzamide (3.3 g).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Methoxy-N-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124610; (2008); A1;,
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Some common heterocyclic compound, 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene, molecular formula is C10H14O3, 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. Recommanded Product: 6443-69-2

Compound 1 (1.82 g, 0.01 mol), NaBr (1.13 g, 0.011 mol) and sulfuric acid (2 mL) weredissolved in ethanol (8 mL). The mixture was treated dropwise with 30% H2O2 (5 mL,0.045 mol) at room temperature over a period of 1 h. Then the mixture was quenchedwith water (10 mL) and extracted with petroleum ether (15mL 3). The organic layerswere combined and evaporated in vacuo to afford 2, 2.60 g, 100%, yellowish oil.IR: (cm1) 3490, 2934, 1570, 1466, 1402, 1109, 824. 1H NMR (400MHz, CDCl3):d 6.61 (s, 1H, ArH), 3.89 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.84 (s, 3H, OCH3),2.37 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3): d 152.2, 150.8, 141.1, 133.4, 110.8,109.5, 61.1 (OCH3), 60.9 (OCH3), 56.1 (OCH3), 23.2(CH3). The spectroscopic data arein accord with the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6443-69-2, its application will become more common.

Reference:
Article; Qiu, Yong-Fu; Yan, Yi-Yu; Lu, Bin; Tang, Lei; Zhai, Yu-Lin; Chen, Ke-Xin; Wang, Jin; Organic Preparations and Procedures International; vol. 51; 6; (2019); p. 602 – 605;,
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Application of 79128-08-8, The chemical industry reduces the impact on the environment during synthesis 79128-08-8, name is 1,3-Diisopropoxybenzene, I believe this compound will play a more active role in future production and life.

2- (2-hydroxy-4-pyrrolidinylbenzoyl) benzoic acid(1-A, 0.015 mmol, synthesized by the method described in Kamino et al., Org. Lett., 2014, 16, 258)And 1,3-diisopropoxybenzene(2-D, 0.074 mmol, synthesized by the method described in Kamino et al., Biorg. Med. Chem. Lett., 2008, 18, 4380)Was added to methanesulfonic acid (5 mL), and the mixture was stirred at 110 C. for 24 hours. The reaction solution was made basic with saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform.After drying the organic layer with magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product was dissolved in chloroform and subjected to silica gel column chromatography to separate the compound ABPX 105-a and the compound ABPX 105-b.At this time, the compound ABPX 105 – a had flowed out first, and then the compound ABPX 105 – b flowed out. The yield was 74% in total of ABPX 105-a and ABPX 105-b. The reaction formula is shown below.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,3-Diisopropoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RIKEN; Kamino, Shinichiro; Sawada, Daisuke; Enomoto, Shuichi; Watanabe, Chikara; (37 pag.)JP2017/88879; (2017); A;,
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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 36805-97-7 as follows. Formula: C11H25NO2

3-Hydroxy Phenyl Acetic Acid-t-butyl Ester (Reagent F) A stirred suspension of 3-hydroxy-phenyl acetic acid (1.52 g, 10 mmol) in anhydrous toluene (20 mL) was heated at 80 C. and N,N-dimethyl formamide-di-t-butyl acetal (9.6 mL, 40 mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were distilled off in vacuo. Th residue was diluted with water and extracted with diethyl ether (*2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent to afford the title compound as a solid (1.17 g, 56%). 1H-NMR (300 MHz, CDCl3):delta 1.47(s, 9H), 3.49(s, 2H), 6.30(s, 1H), 6.70-6.79 (m, 2H), 6.81(d, J=7.6 Hz, 1H), 7.16(t, J=7.7 Hz, 1H).

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan Sales, Inc.; US6252090; (2001); B1;,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-4-fluoro-2-methoxybenzene

To tert-butyl (R)-3-methylpiperazine-1 -carboxylate (5.37 g, 26.8 mmol) and 1 – bromo-4-fluoro-2-methoxybenzene (5.00 g, 24.4 mmol) in toluene (50 ml.) was added sodium tert-butoxide (4.69 g, 48.8 mmol) followed by BrettPhos palladacycle G3 (66.4 mg, 0.0732 mmol). The mixture was sealed under nitrogen and stirred at 100 C and after 1 h the mixture was cooled to ambient temp, diluted with ethyl acetate and water. The organic layer was dried with sodium sulfate, filtered, and concentrated. Crude product was purified by column chromatography (0-40%, ethyl acetate/hexanes) to provide the product. MS(EI) for C; /H:FN;.C. found 325 [M+H]+.

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 450-88-4.

Reference:
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
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Related Products of 6346-09-4, A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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.

N-Fmoc-4-amino-butyraldehyde diethyl acetal4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 16 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification; Procedure 16: Protection of Amine by Fmoc GroupTo a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to O0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion-wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHAOGEN, INC.; BRUSS, Jon, B.; MILLER, George, H.; AGGEN, James, Bradley; ARMSTRONG, Eliana, Saxon; WO2010/132777; (2010); A2;,
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