Category: ethers-buliding-blocks

Electric Literature of 393-15-7,Some common heterocyclic compound, 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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 methyl 5-amino-2-[(4-trifluoromethylphenyl)(phenyl)methoxy]benzoate (300 mg, 0.748 mmol), diisopropylethyl amine (0.149 ML, 0.898 mmol), di(N-succinimidyl) carbonate (230 mg, 0.898 mmol) and acetonitrile (9 ML) was stirred for 1 hour under ice-cooling, diisopropylethyl amine (0.149 ML, 0.898 mmol) and 5-amino-2-methoxybenzotrifluoride (172 mg, 0.898 mmol) were added to the solution under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 12 hours.. The reaction solution was poured into water, extracted with ethyl acetate, was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.. The residue was purified by silicagel column chromatography (hexane:ethyl acetate = 1:1), to obtain the titled compound as a solid. 247 mg (53.5%) 1H-NMR (CDCl3) delta; 3.82 (3H, s), 3.88 (3H, s), 6.24 (1H, s), 6.73 to 7.66 (17H, m)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methoxy-3-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1437344; (2004); 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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5961-59-1

HATU (1.52 g, 4.01 mmol) was added to a stirred solution of 4-methoxy-N-methylaniline (500 mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.01 mmol) iln DMF (20 mL) and DIPEA (1.27 mL, 7.29 mmol) and the reaction mixture was stirred at rt for 4 h. The reaction mixture was concentrated and the crude oil was then partitioned between EtOAc (-60 mL) and 1/2 sat. NaHCCb (aq.) (-60 mL). The organic component was washed with brine (-40 mL), dried (MgS04), filtered and concentrated. The residual oil was then purified using a Biotage Horizon (80g SiC , 10- 40% EtOAc/hexanes) to yield Intermediate 1 (1.34 g) as clear amber viscous oil. LC-MS retention time = 3.17 min; m/z = 285.3 [M+H-Boc]+. (Column: Phenomenex Luna C18 2.0 X 50 mm 3 muiotaeta. Solvent A = 95% Water : 5% Acetonitrile : 10 mM NH4OAc. Solvent B = 5% Water : 95% Acetonitrile : 10 mM NH4OAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 4 minutes, then a 1 -minute hold at 100% B. Wavelength = 220 nm). NMR (400 MHZ, CDCb) delta ppm 7.25 – 7.20 (m, 3H), 7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (app q, J=7.4 Hz, 1H), 3.83 (s, 3H), 3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s, 9H).

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
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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. 2525-16-8, name is 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine

To a solution of ethyl N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-chloro-4-(piperidin-4-yloxy)phenyl]sulfamoylacetate dihydrochloride (0.75 g) obtained in example 47(a) in ethanol (25 ml) were added successively 7-methoxy-3,4,5,6-tetrahydro-2H-azepine (0.39 g) and triethylamine (0.85 ml) at room temperature, and the resulting mixture was stirred at room temperature for 7 hours and then allowed to stand at room temperature for 15 hours.. Because of the slow progress of the reaction, 7-methoxy-3,4,5,6-tetrahydro-2H-azepine (0.22 g) and triethylamine (0.51 ml) were furthermore added successively, and the resulting mixture was stirred at 45C for 12 hours, allowed to stand at room temperature for 11 hours and then furthermore stirred at 45C for 10 hours.. After stirring, to the reaction mixture was added a 4N solution of hydrogen chloride in dioxane (5 ml) and the resulting mixture was evaporated in vacuo.. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 25 % acetonitrile/water).. Subsequently, to a solution of the amorphous solid obtained in ethanol (5 ml) was added a 4N solution of hydrogen chloride in dioxane (2 ml), and the resulting mixture was evaporated to dryness in vacuo.. The residue obtained was dissolved in water and then lyophilized to afford the title compound (0.30 g, yield: 35 %) as a colorless amorphous solid. 1H NMR (400MHz, DMSO-d6) delta ppm: 1.21 (3H, t, J=7.0), 1.52-1.63 (4H, m), 1.68-1.81 (4H, m), 2.04-2.10 (2H, m), 2.84-2.88 (2H, m), 3.36-3.42 (2H, m), 3.62-3.91 (4H, m), 4.18 (2H, q, J=7.0), 4.41 (2H, s), 4.46 (2H, d, J=6.0), 4.81-4.87 (1H, m), 6.44 (1H, dt, J=16.0, 6.0), 6.57 (1H, d, J=16.0), 7.32 (1H, d, J=9.0), 7.40 (1H, dd, J=9.0, 2.5), 7.52- 7.59 (2H, m), 7.66-7.74 (2H, m), 7.88 (1H, s); IR (KBr, cm-1): 1738, 1674, 1628, 1353, 1156.

The synthetic route of 2525-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; EP1375482; (2004); A1;,
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Related Products of 7664-66-6, 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. 7664-66-6 name is 4-Isopropoxyaniline, 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 of 4-isopropoxyaniline (151 mg) in DCM (5 mL) at 0 C was added pyridine (0.243 mL) followed by 3-carbamoyl-4-hydroxy-5-methylbenzene-1 -sulfonyl chloride (lnt-4, 250 mg). The reaction mixture was allowed to warm to RT and was stirred for 16 hr. The reaction mixture was diluted with water (30 mL) and extracted with DCM ( 2 x 50 mL). The combined DCM extracts were washed with saturated brine (25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product. The crude product was washed with diethyl ether (2 x 10 mL) and dried under vacuum to afford the titled compound (212 mg). LCMS m/z 365.09 (M+H)+. NMR (400MHz, DMSO-c/6) delta = 14.33 (br s, 1 H), 9.63 (s, 1 H), 8.74 (br s, 1 H), 8.10 (d, J = 2.2 Hz, 2H), 7.60 (d, J = 1 .3 Hz, 1 H), 6.98 – 6.91 (m, 2H), 6.80 – 6.74 (m, 2H), 4.47 (td, J=6.0, 12.1 Hz, 1 H), 2.15 (s, 3H), 1 .19 (d, J = 5.9 Hz, 6H).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
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Related Products of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1.3. Preparation of SIK inhibitor II-1[00385] In an exemplary experiment, SIK inhibitor II-1 was prepared according to the method shown in Scheme 2. N-(2,6-dimethylphenyl)-1H-imidazol-2-amine[00386] To a solution of cyanogen bromide (25 g, 236.03 mmol) in hexane (80 mL) was added a solution of the amino-acetaldehyde diethyl acetal (34.3 mL, 236.03 mmol) in diethyl ether (80 mL) at room temperature. The resulting mixture was stirred overnight. A white solid was formed and was removed by filtration and washed with diethyl ether. The filtrate was concentrated and purified by flash chromatography on silica gel (eluted with 0/100 to 5/95 methanol/dichloromethane) to afford N-(2,2-diethyloxyethyl)carbodiimide (27 g, 72% yield) as a bright yellow oil. Rt (retention time) = 1.82 min; MS m/z: 159.20 [M+1].

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

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; THE BROAD INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION D/B/A MASSACHUSETTS GENERAL HOSPITAL; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; SHAMJI, Alykhan; SUNDBERG, Thomas; GRAY, Nathanael; XAVIER, Ramnik; SCHREIBER, Stuart, L.; CHOI, Hwan, Geun; LIANG, Yanke; (315 pag.)WO2016/23014; (2016); A2;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Roundbottom flask is charged with 5-bromo-2-methylaniline ( 100.00 mg; 0.54 mmol; 1 .0 eq), methanol (1.5 mL), 37 % formaldehyde solution in methanol (289.18 mg; 3.56 mmol; 2.40 eqf.) and acetic acid (104.68 mg; 1.29 mmol; 2.40 eq.). RM is stirred at room temperature for 10 minutes. After this time RM is cooled down to 0C and sodiumcyanoborohydride (70.93 mg; 1 .13 mmol; 2.10 eqf.) is added. Reaction mixture is stirred in this temperature for 1 h. Then the solvent is evaporated and reaction is quenched with saturated aqueous solution of NaHC03 (5 mL) and extracted with DCM ( 3×5 mL). Combined organic extracts are washed with water (2×10 mL). Organic solvent is then evaporated and crude product is further purified by FCC(DCM/EtOAc, gradient) to 5-bromo-N,N,2-trimethylaniline (74.20 mg; yield 61.6 %; 95.5 % by UPLC) as a colorless oil.

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; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
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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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

Example 22; Part A:To a solution of 4-(methylsulfonyl)phenylhydrazine (5.0 g, 26.8 mmol, 1.00 equiv) and 1 ,1 ,3,3-tetramethoxypropane (4.4 ml_, 26.8, 1.0 equiv) in ethanol (37 ml_) at rt was added concentrated HCI (2.8 mL). The resulting solution was heated at reflux for 1 hr, cooled to 0 0C and filtered to give 1-(4-methanesulfonyl-phenyl)-1/-/- pyrazole as a yellow solid (4.73 g, 79%). LCMS: (MH)+ = 223.1 (1.19 min).

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 102-52-3.

Reference:
Patent; SCHERING CORPORATION; WO2008/82487; (2008); A2;,
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Related Products of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, 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: To a solution of compound 1a-e (10.0 mmol,1.0 eq) in anhydrousTHF (20 mL) was slowly added n-BuLi (6 mL of 2.5 M solution inhexane, 15.0 mmol, 1.5 eq) at 78 C. The mixture was stirred for1 h and triisopropyl borate (50.0 mmol, 5.0 eq) was added by syringe.The solutionwas stirred for another 1 h and allowed towarmto 25 C overnight. The reactionwas cooled to 0 C, followed by thesequential addition ofwater (5 mL) and 2N HCl (5 mL). After 10 min,an additional 35 mL of 2N HCl was added and the mixture wasfurther stirred for 30 min. The mixture was extracted with ethylacetate (20 mL * 3) and the combined organic layers wereconcentrated to a thick oil under reduced pressure. Crystallizationwith cold hexane yielded a white solid.

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Yali; Han; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8FNO

Example 104 Synthesis of 6-Chloro-N,N’-bis-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine (E15) To 124 (1.09 g, 3.5 mmol) dissolved in acetone (25 mL) was added 3-fluoro-p-anisidine (0.54 g, 3.5 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.4 mL, 3.5 mmol) and water (3.5 mL). The reaction mixture was stirred and heated at reflux for 3 hours. The reaction mixture was extracted three times using dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was filtered, concentrated in vacuo, and the resulting solid was dried overnight under vacuum to yield white solid (E15) (1.332 g, 97percent); mp 194° C.; HPLC: Inertsil ODS 3V C18, 40:30:30 v:v:v [KH2PO4 (0.01 M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 33.2 min, 97.6percent purity; MS (TOF ES+) m/z 396 (35.0); 394 (M+H, 100).

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; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Reddy, Velagala Venkira Rama Murali Krishna; Sridevi, Bhatlapenumarphy Shesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/224950; (2004); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: ((3-Bromopropoxy)methyl)benzene

To a suspension of NaH (55 wt percent in oil, 253 mg, 5.8 mmol) in DMF (12 mL) was added 3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine (9) (1.4 g, 5.1 mmol) in DMF (12 mL) at 0 °C. After stirring for 10 min at room temperature, the mixture was cooled to 0 °C, and then benzyl 3-bromopropyl ether (1.37 g, 5.8 mmol) was added. The mixture was stirred for 1 h at room temperature, then 10percent aq NH4Cl and ethyl acetate were added to the reaction mixture. The mixture was extracted with ethyl acetate 2 times, and the combined extracts were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The residual paste was chromatographed on silica gel (AcOEt/hexane) to afford (10) as a colorless oil (1.71 g, 79percent yield).1H NMR (CDCl3, delta ppm): 6.85-7.47 (12H, m), 4.43 (2H, s), 3.80 (2H, t, J = 6.4 Hz), 3.46 (2H, t, J = 6.0 Hz), 2.92-3.10 (4H, m), 1.77-1.92 (2H, m).

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; Kubota, Katsumi; Kurebayashi, Hirotaka; Miyachi, Hirotaka; Tobe, Masanori; Onishi, Masako; Isobe, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 3005 – 3021;,
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