Category: ethers-buliding-blocks

148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, 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 C9H12FNO

Intermediate 29 Ethyl 7-chloro-4-{[4-fluoro-2-(propan-2-yloxy)phenyl]amino}-5-methyl^ d]pyrimidine-6-carboxyla te A mixture of Intermediate 28 (320 mg, 1.17mmol), 4-fluoro-2-isopropoxyaniline (179 muIota, 1.17 mmol) and PTSA (22 mg, 0.117 mmol) in IPA (15 ml) was stirred and heated at 60″C for 3 hours. The reaction was allowed to cool to rt and then concentrated to dryness. The residue was diluted with DCM and washed with sat. NaHCOs (aq). The aqueous phase was re-extracted with DCM. The combined organic phases were dried and concentrated. The crude product was pre-absorbed on to silica gel prior to purification by flash chromatography on silica gel eluting with 40:1 DCM: IPA to give a pale beige coloured solid (395 mg, 83 %). 1H NMR (400 MHz, DMSO-d6) delta ppm 1 ,27 (d, J=5.95 Hz, 6 H), 1.38 (t, J=7.10 Hz, 3 H), 4.31 (s, 3 H), 4.37 – 4.47 (m, 2 H), 4.73 (dt, J=12.02, 6.13 Hz, 1 H), 6,77 – 6.86 (m, 1 H), 7.07 (dd, J=10.99, 2.75 Hz, 1 H), 8.27 (dd, J=8.70, 6.41 Hz, 1 H), 8.38 (s, 1 H), 8.43 (s, 1 H)

The synthetic route of 148583-65-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; WINTER-HOLT, Jon James; MCIVER, Edward Giles; LEWIS, Stephen; OSBORNE, Joanne; (106 pag.)WO2017/85483; (2017); A1;,
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Electric Literature of 1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

Synthesis of Compound 113To a stirred solution of compound 1703 (200 mg, 1.26 mmol) in DCM (10 rnL) was added N-methylmorpholine (0.41 rnL, 3.79 mmol) and 3-benzyloxy-phenylamine (251 mg, 1.26 mmol) at 00C. The reaction mixture was stirred at room temperature overnight. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under vacuum to remove DCM. The residue was dissolved in water and extracted with ethyl acetate (2 x 50 mL), and the organic layer was washed with brine and dried over anhydrous sodium sulfate to afford coupled product 113 (120 mg, 28percent) with HPLC purity of 91.4percent. Mass: 340 [M+H]; 1H NMR (500 MHz, CDCl3): delta 1.35 (m, 5H), 1.6-1.85 (m, 6H), 4.1 (d, IH), 5.1 (s, 2H), 6.78 (m, IH), 7.08 (m, IH), 7.2-7.6 (m, 7H), 8.38 (s, IH).

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

Reference:
Patent; ARETE THERAPEUTICS, INC.; WO2008/73623; (2008); A2;,
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Application of 216067-66-2,Some common heterocyclic compound, 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, molecular formula is C9H13NO3, 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.

INTERMEDIATE 3 Preparation of 5- (3-Formvl-ph)-furan-2-carboxylic acid 2 4-dimethoxv-benzyloxv)- amide The title compound was made by method analogous to INTERMEDIATE 2. Alternatively, it was also made by the following method. The acid (25) which was made by method analogous to INTERMEDIATE 1, was reacted with protected hydroxylamine (24) by using N, N’-Dicyclohexylcarbodiimide (DCC) as coupling reagent. The resulting bromide (26) was used for Suzuki coupling to give the title compound (28).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route O-(2,4-Dimethoxybenzyl)hydroxylamine, its application will become more common.

Reference:
Patent; S*BIO PTE LTD; WO2005/40161; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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 18800-30-1, HPLC of Formula: C8H8Br2O

4-(4-methoxybenzoyl)piperidine (1.2 g, 5.3 mmol),1-(2-Bromoethoxy)-4-bromobenzene (1.9 g, 6.9 mmol), KI (1.6 g, 10 mmol) and 30 mL of ethanol were added to a 100 mL eggplant-shaped flask and heated under reflux, and 5 mL of a 20% KOH solution was added dropwise.The addition was completed in 10 minutes. Reflux for 24 hours, evaporate the solvent and dissolve in 30 mL of dichloromethane.The organic layer was washed three times with 20 mL of water, and the organic layer was concentrated.A mixture of ethyl acetate and petroleum ether was used as the eluent.Column chromatography gave 0.60 g of pale yellow solid with a yield of 27.8%

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-Bromo-4-(2-bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Southeast University; Zhong Yan; Fang Tiantian; Chen Liyi; (24 pag.)CN110437136; (2019); A;,
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1663-61-2, name is (Triethoxymethyl)benzene, 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 1663-61-2

EXAMPLE IV 1-acetyl-5-butyryl-3-(ethoxy-phenyl-methylidene)-2-indolinone 10 g (49 mmol) 5-butyryl-2-indolinone (Ex. 1.2) are stirred in 200 ml acetic anhydride for 5 h at 130¡ã C. Then 35 ml triethyl orthobenzoate are added and the mixture is stirred for a further 4 h at 100¡ã C. Then it is evaporated down and the resulting precipitate is suction filtered, washed and dried. Yield: 11.5 g (62percent of theory) Rf=0.79 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2) C23H23NO4 (MW=377.438) Mass spectrum: m/z=378 (M+H)+

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209302; (2005); A1;,
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Related Products of 21388-17-0,Some common heterocyclic compound, 21388-17-0, name is 2-Ethyl-6-methoxynaphthalene, molecular formula is C13H14O, 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.

EXAMPLE 9 Preparation of 2-Methoxy-6-(1-Bromoethyl) Naphthalene: A mixture of 1.0 gram of 2-methoxy-6-ethylnaphthalene and 1.05 grams of N-bromosuccinimide in 10.0 ml. of carbon tetrachloride was refluxed for 1 hour. During this time, the solids migrated from the bottom of the reaction flask to the top. The mixture was cooled to room temperature and the solids were separated from the liquid by filtration on a small suction filter funnel. The carbon tetrachloride solvent was removed using a rotary vacuum evaporator. The yield was 1.55 grams of a pale oil that solidified at room temperature. Based on 1 H nuclear magnetic resonance data, the product had a structure consistent with that of 2-methoxy-6- (1-bromoethyl) naphthalene.

The synthetic route of 21388-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amoco Corporation; US5235115; (1993); A;,
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Synthetic Route of 102-52-3, A common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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 glass-made reactor (inside volume: 2L) equipped with a condenser, thermometer, gas-blowing tube and stirrer was charged with 500 g of 2-methoxy ethanol, into which 36.5 g (1.00 mol) of hydrogen chloride gas was blown at 15C in 1 hour to be dissolved therein, and then 82.0 g (0.50 mol) of malondialdehyde bisdimethylacetal(1,1,3,3-tetramethoxypropane) was added at 10C. Then, 137.0 g (1.10 mols) of 2,3-dimercapto-1-propanol was added immediately to the above mixture at the same temperature, and the resultant mixture was stirred at 25C for 12 hours. After the starting compound was confirmed to disappear by gas chromatography, the reaction mixture was added, with stirring, to 1000 g of water in 30 minutes. The resultant mixture was subjected to extraction with chloroform and washing with water, and separation to obtain an organic phase. Chloroform was distilled at 45C under a vacuum to obtain a singly yellowish, transparent liquid crude product. The crude product thus prepared was purified by silica gel column chromatography (developing solvent: using mixed solvent of toluene/ethyl acetate: 60/40), to obtain 92.4 g (0.325 mol) of the dihydroxy compound represented by the following formula, which was a lightly yellowish crystal, as Example Compound No. (2-a-2). Its yield was 65% on malondialdehyde bisdimethylacetal as the starting compound. ? 270MHz 1H-NMR delta (CDCl3); 2.18 to 2.33 (m, 2H), 3.15 to 3.38 (m, 4H), 3.42 to 3.68 (m, 4H), 3.72 to 3.88 (m, 2H), 4.47 (dq, 2H), 4.72 to 4.78 (m, 2H) ? EI-MS: 284(M)

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsui Chemicals, Inc.; EP1388540; (2004); 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., COA of Formula: C7H16O4

Example A4 Preparation of the Compound of Formula 70.67 grams of piperidine are condensed with 1,1,3,3-tetramethoxypropane in acetic acid, concentrated and treated with 59.72 grams of 2-ethoxyethyl cyanoacetate cyanoacetate in the presence of an organic base and a solvent. [0228] The following base/solvent combinations are used:The desired product (104) is obtained in yields of 91% (96.5 grams) as an orange powder. [0230] After silica gel column chromatography (eluent: toluene/acetone) the pure product (104) is obtained yielding dark yellow crystals. [0231] Melting point: 66-67 C.

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; Winkler, Barbara; Hueglin, Dietmar; Eichin, Kai; Ehrsam, Larissa; Marat, Xavier; Richard, Herve; Kienzle, ILona Marion; Schroeder, Ute; US2014/150380; (2014); A1;,
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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 29578-39-0 as follows. COA of Formula: C7H6BrFO

To a suspension of sodium hydride (60% in mineral oil, 600 mg, 15.0 mmol) inDMF (20 mL) at 65 C was slowly added a solution of 4-hydroxy-l -methylpiperidine (1.15 g, 10 mmol) in DMF (7.0 mL). After stirring for 30 minutes, a solution of 3-bromo-5-fluoroanisole (2.05 g, 10 mmol) in DMF (7.0 mL) was added and the reaction mixture was stirred at 65 C for 24 h. The reaction mixture was allowed to cool to ambient temperature then was poured into water (200 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were loaded onto a SCX-2 cartridge, which was then washed with acetonitrile then eluted with 2N ammonia in methanol. Concentration of the basic methanolic fractions in vacuo gave the title compound (1.5 g, 50%). 1H NMR (CDCl3, 400MHz): 6.65 (dd, J = 2.2, 1.6Hz, 1H), 6.63 (dd, J = 2.3, 1.6Hz, 1H), 6.37 (dd, J = 2.3, 2.1Hz, 1H), 4.29-4.21 (m, 1H), 3.75 (s, 3H), 2.70-2.61 (m, 2H), 2.31-2.21 (m, 5H), 2.01-1.93 (m, 2H), 1.86-1.75 (m, 2H). LCMS (Method B): RT = 2.1 min, M+H+ = 300.

According to the analysis of related databases, 29578-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; WO2009/151598; (2009); 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. 32338-02-6, name is 2-Bromo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 32338-02-6

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 ¡ãC for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

According to the analysis of related databases, 32338-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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