Ethers-buliding-blocks

Synthetic Route of 19500-02-8, These common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-methylaniline, 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.

The 15.0g of 3-amino-1-methoxy-2-methyl, 48.7g of triphosgene and 350 ml of toluene in a mixture of the heating to reflux with stirring 3 hours. Cooling the reaction mixture, the concentrated under reduced pressure, to obtain 17.0g of 1-methoxy-3-isocyanato-2-methylbenzene (called below 4A).

Statistics shows that 3-Methoxy-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 19500-02-8.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Takayuki, Shiota; Masaki, Arimori; (241 pag.)CN105492432; (2016); A;,
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Reference of 31576-51-9,Some common heterocyclic compound, 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, molecular formula is C5H13NO2, 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 4-thioxo-l, 3-thiazolidin-2-one (2.24 g) in ethanol (20 mL) was added 2- (2-methoxyethoxy) ethanamine (2.5 g), and the mixture was stirred at room temperature for 5 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(ethyl acetate) to give the title compound (3.1 g) .XH NMR (300 MHz , CDC13) delta 3.43 (3H, s) , 3.48-3.63 (2H, m) , 3.63-3.83 (6H, m) , 4.13 (2H, s) , 6.83 (1H, brs) .MS (ESI+) : [M+H]+ 219.1.

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MATSUMOTO, Shigemitsu; ONO, Koji; TOMINARI, Yusuke; KATOH, Taisuke; MIWA, Kazuhiro; HASUOKA, Atsushi; IMAMURA, Shinichi; WO2013/18929; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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 29578-83-4, Computed Properties of C8H9BrO

Add 1-bromo-3-methoxy-5-methylbenzene 4a (22.8 g, 113 mmol) to the eggplant-shaped bottle, and dissolve in methylene chloride (100 mL) Add N-bromosuccinimide (242 g, 136 mmol) and azobisisobutyronitrile (31.5 g, 192 mmol) and heat to 45 C under reflux overnight. After the reaction is over,The reaction was returned to room temperature and extracted with ethyl acetate (40 mL x 3).The organic phase was washed with water (40 mL x 2) and brine (40 mL * 2),It was then dried over anhydrous sodium sulfate, filtered and concentrated.The obtained crude product was separated by a normal-phase silica gel column (petroleum ether: ethyl acetate = 20: 1) to obtain 1-bromo-3-(bromomethyl)-5-methoxybenzene 4b (20 g, yellow solid), yield : 63%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shanghai Meidixi Bio-pharmaceutical Co., Ltd.; Meidixipuya Pharmaceutical (Shanghai) Co., Ltd.; Ren Feng; Wang Xianlian; Xu Yongmei; Chen Chunlin; Cai Jinna; (28 pag.)CN110194773; (2019); A;,
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366-99-4, name is 3-Fluoro-4-methoxyaniline, 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. Computed Properties of C7H8FNO

Cyanuric chloride (11.07 g, 60 mmol) was dissolved in 40 mL CH3CN and was cooled to about -20° C. To this was added DIEA (11.5 mL, 60 mmol) followed by 3-fluoro-4-methoxyaninline (8.47 g, 60 mmol) in 20 mL CH3CN (reaction froze). The reaction was allowed to warm to room temperature after about 1 hour at -20° C. TLC (2percent CH3OH/CH2Cl2) and mass spectroscopy indicated the presence of the compound 124. The reaction mixture was cooled to about 0° C. before adding DIEA (11.5 mL, 66 mmol). 2-Aminomethyl-1-ethylpyrrolidine (7.77 g, 60 mmol) in CH3CN (10 mL) was added. The reaction was allowed to warm to rt and stirred overnight. Then DIEA (11.5 mL, 66 mmol) and S-(+)-2-methoxyethylpyrrolidine (6.91 g, 60 mmol) in 20 mL 1,4-dioxane were added. The reaction was heated at about 50° C. overnight. The solvent was removed in vacuo, and the resulting residue was purified by flash chromatography on silica gel packed in ethyl acetate. The front running impurities were removed and subsequently the eluent was increased in polarity to 10percent CH3OH:ethyl acetate. The material collected from the column was then dissolved in water and extracted in CH2Cl2 (4 times), dried over MgSO4, and concentrated to dryness to give a brown solid 145 (9.7 g, 27.6percent yield), 71-72° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 5.37 min, 90.3percent purity; 1H NMR (600 MHz, CDC3, 55° C.) delta 7.69 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.86 (t, J=9 Hz, 1H), 4.29 (s, 1H), 3.90-3.96 (m, 1H), 3.84 (s, 3H), 3.63-3.81 (m, 6H), 3.35 (s, 3H), 3.23-3.25 (m, 1H), 2.85 (broad s, 1H), 2.78 (broad s 1H), 2.14 (broad s, 2H), 1.89-2.04 (m, 6H), 1.37 (apparent t, J=7.2 Hz, 3H); 13C NMR (150.8 MHz, CDCl3, 55° C.) delta 165.8, 163.8 (2C), 152.3 (d, Jc-f=243.5 Hz), 143.0 (142.9, rotamer or diastereumer), 133.7 (133.67, rotamer or diastereomer), 115.0, 114.4, 109.1 (108.9, rotamer or diastereomer), 72.8, 66.6, 59.0, 57.0, 56.6, 53.7, 51.0, 46.8, 42.2, 28.4 (28.2, rotamer or diastereomer), 23.1 (23.0, rotamer or diastereomer), 10.9; MS (ESI) mn/z 460.2 (M+H, 44.7), 251.1 (47.7), 235.1 (27.5), 231.1 (37.4), 230.6 (100), 214.6 (36.5).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
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Related Products of 456-55-3,Some common heterocyclic compound, 456-55-3, name is (Trifluoromethoxy)benzene, molecular formula is C7H5F3O, 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.

(iv) 4-Trifluoromethoxy-alpha,alpha,alpha-trifluoroacetophenone, from 4-bromotrifluoromethoxybenzene 4-Bromotrifluoromethoxybenzene may be prepared from trifluoromethoxybenzene by the process described in the Journal of Organic Chemistry, 29, 1, (1964). Boiling point: 164-166 C. (atmosphere pressure). 1 H NMR (CDCl3) (ppm): 7.35, 8.14 (4H,d) 19 F NMR (CDCl3) (ppm relative to CFCl3): -58.1 (s) CF3 O -72.1 (s) CF3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; Imperial Chemical Industries PLC; US5225607; (1993); A;,
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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. 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Methoxy-2-methylpropan-1-amine

A mixture of phenyl 5-({trans-4-[(2-chloro-4-fluoro-5-methylphenyl)carbamoyl]cyclohexyl}carbamoyl)- 1 H-im idazole-4-carboxylate (100 mg, 0.200 mmol) and 2-methoxy-2-methylpropan-1 -amine (103 mg, 1 .00 mmol, GAS No 89282-70-2) in tetrahydrofuran (5.0 ml) was stirred at 60CC over nigh t. For work-up, the reaction mixture wasconcentrated and the residue was purified by preparative HPLG (Method 9) to yield the title compound (48.0 mg, 48% yield).LG-MS (Method 3): R = 1 .16 mm; MS (ESIpos) m/z = 508.3 [M+H].1HNMR (400 MHz, DMSO-d6): 6[ppm] = 13.37-13.15 (m, 1H), 11.22-1 0.96 (m, 1H), 9.46 (br.s., 1 H), 8.47-7.96 (m, 1 H), 7.83 (5, 1 H), 7.50 (d, 1 H), 7.41 (d, 1 H), 3.90-3.56 (m, 1 H), 3.37 (d,2H), 3.15 (br. s., 3H), 2.21 (d, 3H), 2.14-1.79 (m, 4H), 1.64-1.47 (m, 3H), 1.40-1.21 (m, 1H),1.14 (5, 6H).

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 89282-70-2.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); 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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H8BrFO

Step 1. 5-[2-(4-fluoro-phenoxy)-ethoxy]-tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-one A mixture of 2-hydroxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[a][8]annulen-11-one (21.7 g; J. Org. Chem 1982, 47, 4329), K2CO3 (17.7 g) and 1-(2-Bromo-ethoxy)-4-fluoro-benzene (40.3 g) in DMF (400 ml) were stirred for 72 hours at 120 C. The reaction was then cooled to room temperature and the solvent removed in vacuo. The residue was then washed with saturated NaHCO3 solution and the organics extracted with EtOAc (3*200 ml). The organics were then combined, dried (MgSO4) and the solvent removed in vacuo yielding a dark brown oil which was purified by flash chromatography on silica eluding 20% EtOAc in isohexane giving the title alkylated ketone (15.97 g, 44%). MS (ES+) 341 [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; Belanger, Patrice Charles; Collins, Ian James; Hannam, Joanne Claire; Harrison, Timothy; Lewis, Stephen John; Madin, Andrew; McIver, Edward Giles; Nadin, Alan John; Neduvelil, Joseph George; Shearman, Mark Steven; Smith, Adrian Leonard; Sparey, Timothy Jason; Stevenson, Graeme Irvine; Teall, Martin Richard; US2004/29862; (2004); A1;,
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Adding some certain compound to certain chemical reactions, such as: 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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 19056-40-7. 19056-40-7

Method 12 2-[(4-Bromo-3-methoxyphenyl)diazenyl]-2-cyanoacetamide. Sodium nitrite (8.54 g, 123.7 mmol) dissolved in water (100 ml) was added to an ice- cold suspension of 4-bromo-3-methoxyaniline (25 g, 123.7 mmol) in concentrated HCl (46 ml, 1514 mmol) and water (100 ml). After stirring for 10 minutes, 2-cyanoacetamide (10.40 g, 123.7 mmol) and sodium acetate trihydrate (84 g, 617 mmol) in water (1.8 L) was added and the reaction was allowed to stir overnight. The resulting solid was collected by filtration, washed with water, dried, giving an orange solid which was refluxed in 1.4 L of ethanol for 30 min. The mixture was cooled to room temperature, the solid was collected by filtration, washed with ethanol (100 ml x 3), and dried to yield the title compound as a yellow solid (34.4 g, 94 percent). 1H NMR: 11.70 (s, 1 H), 7.90 (s, 1 H), 7.50 (m, 2 H), 7.35 (s, 1 H), 7.20 (d, 1 H), 3.90 (s, 3 H); m/z: 296.

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 4-Bromo-3-methoxyaniline.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/90353; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, 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 103291-07-2, 103291-07-2

To a solution of 69A (2.7 g, 13.1 mmol) in THF (25 mL) at -78 C. was added n-BuLi (1.6 M in hexanes, 11.0 mL, 17.7 mmol). The mixture was stirred at -78 C. for 40 min before trimethyl borate (2.7 mL, 24.3 mmol) was added. The reaction was left stirring from -78 C. to rt over 18 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 69B (0.75 g, 35% yield) was collected as a white solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 3.86 (s, 3 H) 7.03-7.45 (m, 3 H).

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, 4-Bromo-1-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/3539; (2007); 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. 57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C13H10F3NO

To a solution of 4-(4-(trifluoromethyl)phenoxy)aniline (AK Scientific, 63 mg, 0.25 mmol) in DCM 2-chloroacetyl chloride (Sigma, 34 mg, 0.30 mmol) and triethylamine (Sigma, 30.4 mg, 0.30 mmol) were added and the reaction stirred overnight. Upon reaction completion the crude was purified by silica gel chromatography (10-40% EtOAc/hexanes) to yield 65 mg (78%).1H NMR (400 MHz, CDCl3): d 8.25 (s, 1H), 7.63- 7.51 (m, 4H), 7.12- 6.99 (m, 4H), 4.22 (s, 2H). HRMS: (-ESI): calcd. for: C15H10O2NF3Cl = 328.0358, found: 327.0356

The synthetic route of 57478-19-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; NOVARTIS AG; SPRADLIN, Jessica; WARD, Carl, C.; NOMURA, Daniel, K.; SCHIRLE, Markus; TALLARICO, John, A.; MCKENNA, Jeffrey; MAIMONE, Thomas, John; HU, Xirui; (472 pag.)WO2020/76996; (2020); A1;,
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