Tag: M.W=100-200

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. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

A suspension solution of N-(1,5-dimethylpyrazol-3-yl)-2-fluoro-3-(trifluoromethyl)benzamide (0.50 g), 55% sodium hydride (0.07 g) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 5 minutes. To this mixture, 2-ethoxyethyl bromide (0.38 g) and sodium iodide (catalytic quantity) were added and stirred for 17 hours. To the reaction solution, water was added and the reaction solution was extracted with ethyl acetate and then concentrated under vacuum. The residue obtained was purified by silica gel column chromatography (developing solvent: chloroform_methanol=18:1) to obtain a colorless solid substance of N-[1,2-dihydro-1,5-dimethyl-2-(2-ethoxyethyl)pyrazol-3-ylidene]-2-fluoro-3-(trifluoromethyl)benzamide (0.01 g). 1H-NMR, Mass and the melting points of these compounds are shown in Table 11.

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; TAISHO PHARMACEUTICAL CO., LTD; EP1820504; (2007); A1;,
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These common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, 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. Safety of 2-Phenoxyaniline

A solution of sodium nitrite (9.2 g, 0.135 mol) in water (20 ml) was added dropwise to a solution of 2-phenoxyaniline (25 g, 0.135 mol) in 40percent hydrobromic acid (50 ml) at 0° C. and stirred for another 10 minutes. Then the reaction mixture was added to the boiling mixture of cuprous bromide (21.3 g, 0.149 mol) in 40percent hydrobromic acid (50 ml) and after addition it was allowed to reflux for another 30 minutes. Reaction mixture was cooled, diluted with water and extracted with diethyl ether. The diethyl ether layer was washed with 5percent hydrochloric acid, 10percent potassium hydroxide, water, brine, dried over sodium sulfate and concentrated to give the crude intermediate. The sub.-title compound (14.8 g, 45percent) was obtained by column purification of the crude intermediate using pet ether as eluent

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

Reference:
Patent; ASTRAZENECA AB; US2008/15237; (2008); A1;,
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These common heterocyclic compound, 107622-80-0, name is (4-Phenoxyphenyl)methanamine, 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. Computed Properties of C13H13NO

General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).

The synthetic route of (4-Phenoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
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Some common heterocyclic compound, 82172-73-4, name is O-(2-Methoxyethyl)hydroxylamine hydrochloride, molecular formula is C3H10ClNO2, 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: C3H10ClNO2

Example 6-7 [0239] The Z isomer of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone O-(2-methoxyethyl)oxime may be prepared in the following manner: [0240] A suspension of 0.74 g of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone and 0.70 g of O-(2-methoxyethyl)hydroxylamine hydrochloride in 50 cm3 of pyridine is refluxed for about 7 hours. The solution obtained is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 150 cm3 of dichloromethane. The solution is washed with three times 80 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). The mixture of the Z and E isomers is separated by flash chromatography on a column of silica [eluent: dichloromethane/methanol (98/2 by volume)], collecting 60 cm3 fractions. [0241] Fractions 111 to 135 are combined and concentrated to dryness under reduced pressure (13 kPa). 0.37 g of the Z isomer of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone O-(2-methoxyethyl)oxime, corresponding to Example 6-7A, is thus obtained in the form of a resin, the characteristics of which are as follows: [0242] 1H NMR spectrum: (300 MHz, (CD3)2SO d6 with addition of a few drops of CD3COOD d4, delta in ppm): from 0.70 to 0.90 (mt: 4H); 1.81 (mt: 1H); 3.22 (s: 3H); 3.40 (s: 2H); 3.56 (t, J=5.5 Hz: 2H); 4.13 (t, J=5.5 Hz: 2H); 6.25 (d, J=10 Hz: 1H); 6.89 (d, J=10 Hz: 1H); from 7.10 to 7.30 (mt: 10H). [0243] IR spectrum (solvent CCl4) [0244] 3459; 3316; 2932; 2882; 1597; 1492; 1446; 1386; 1291; 1145; 1126; 1069; 1027; 1007; 952; 894; 700; 683 and 541 cm-1 [0245] O-(2-Methoxyethyl)hydroxylamine hydrochloride may be prepared as described by Dae-Kee Kim et al., J. Med. Chem., 40, 15, 1997, 2363-2373.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 82172-73-4, its application will become more common.

Reference:
Patent; Aventis Pharma S.A.; US2004/162276; (2004); 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 20781-20-8 as follows. Recommanded Product: (2,4-Dimethoxyphenyl)methanamine

To a solution of 2,4-dimethoxybenzylamine (Sigma-Aldrich) (6.6 mL, 43.5 mmol) in DCM (85 mL) was added saturated aqueous sodium bicarbonate solution (85 mL) and the mixture was stirred vigorously at RT for 15 min. Stirring was stopped; then thiophosgene (6.6 mL, 87 mmol) was added via syringe to the bottom layer. The mixture was stirred at RT for 90 min then the aqueous layer was separated and the organic layer was washed with brine, dried over Na2S04 and concentrated in vacuo twice from DCM to give l-(isothiocyanatomethyl)-2,4- dimethoxybenzene

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KHAN, Tanweer; SMITH, Elizabeth; WILLIAMS, Peter; WISCOUNT, Catherine; MCKITTRICK, Brian; MCCAULEY, John; (72 pag.)WO2018/106519; (2018); A1;,
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78531-29-0, name is 1,3-Dimethoxypropan-2-amine, 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. Quality Control of 1,3-Dimethoxypropan-2-amine

General procedure: Example 6B (0.018 g, 0.05 mmol) was dissolved in acetonitrile (0.5 ml), and treated with potassium carbonate (0.021 g, 0.15 mmol) and 1 -(2-chloroethyl)pyrrolidine (0.017 g, 0.1 mmol). The reaction mixture was heated via microwave at 180 C for 30 minutes, concentrated in vacuo, and submitted to reverse-phase HPLC (as described in Example 6C) to provide the title compound.

The synthetic route of 78531-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; SWEIS, Ramzi F.; CURTIN, Michael L.; PLIUSHCHEV, Marina A.; HANSEN, Todd M.; LONGENECKER, Kenton; WO2013/170118; (2013); A1;,
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Reference of 349-65-5,Some common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(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.

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
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150-78-7, name is 1,4-Dimethoxybenzene, 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. Application In Synthesis of 1,4-Dimethoxybenzene

Paraformaldehyde (Aldrich, 4.27 g, 144.75 mmol) and HBr/AcOH (Fluka, 33%, 30 mL) were added slowly to a stuffed solution of 1,4-dimethoxybenzene (Aldrich, 10.00 g, 72.37 mmol) in glacial acetic acid (Fisher, 50 mL). The mixture was stirred at 50C for one hour, allowed to cool to room temperature, and then hydrolyzed in water (200 mL). The white solid was collected by filtration, suspended in CHC13 (50 mL), and refluxed for 10 mm. After cooling to room temperature, the white solid was again collected by filtration and washed with water (15.75 g, 67%). NMR spectra were obtained experimentally to confirm the chemical structure of the resulting compound and its purity. NMR results were as follows: ?H NMR (300 MHz, CDC13) 6:6.88 (s, 2H), 4.54 (s, 4H), 3.87 (s, 6H) ppm.

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROBERT BOSCH GMBH; MARUNIAK, Autumn; AHMAD, Habib; RAGHUNATHAN, Ashwin; JOHNSON, Christopher; KAVUSI, Sam; FOMINA, Nadezda; LANG, Christoph; (170 pag.)WO2017/5587; (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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., COA of Formula: C9H13NO

B) (4S)-Lambda/-((1 S)-1-r4-(methyloxy)phenyllethyll-3.4-dihvdro-2H-pyranor3.2-lpyridin-4- amine: To a solution of crude 2,3-dihydro-4/-/-pyrano[3,2-]pyridin-4-one (2.43 g) in 1 ,2- dichloroethane was added {(1S)-1-[4-(methyloxy)phenyl]ethyl}amine EPO (2.49 g, 16.5 mmol) and acetic acid (1.4 ml_, 24.5 mmol). The reaction mixture was stirred for 1 hour, then sodium triacetoxyborohydride (5.18 g, 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours, then diluted with dichloromethane and quenched with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 10% aqueous NH4OH in acetonitrile) provided (4S)- Lambda/-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-3,4-dihydro-2/-/-pyrano[3,2-/j]pyridin-4-amine (1.90 g, 38% two step yield) as a brown oil. 1H NMR (400 MHz, CDCI3) delta 8.15 (dd, J = 3.0, 3.0 Hz, 1 H), 7.35 (d, J = 8.6 Hz, 2 H), 7.07 (d, J = 2.8 Hz, 2 H), 6.86 (d, J = 8.7 Hz, 2 H), 4.19 (ddd, J = 11.0, 7.7, 3.3 Hz, 1 H), 4.07 (q, J = 6.5 Hz, 1 H), 4.00 (ddd, J = 11.1 , 7.3, 3.5 Hz, 1 H), 3.91 (t, J = 5.7 Hz, 1 H), 3.80 (s, 3 H), 2.32 (br, 1 H), 1.70 (m, 2 H), 1.44 (d, J = 6.6 Hz, 3 H).

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
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These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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. Quality Control of 2-Fluoro-1,4-dimethoxybenzene

To a solution of 2-fluoro-l,4-dimethoxybenzene (8.1 g, 52.0 mmol) in anhydrous THF at -78 C, n-BuLi (2.5 M in hexane, 22 mL, 55 mmol) was added dropwise. The resulting mixture was stirred at -78 C for 1 h, and then ethyl chloroformate (5 mL, 52.1 mmol) was added dropwise. The reaction mixture was stirred at -78 C for additional 2 h and quenched with water (200 mL). The mixture was extracted with ethyl acetate (2×180 mL). The combined organic layers were washed with brine (200 mL), dried (Na2S04), and concentrated in vacuo. The residue was purified by silica gel column chromatography (1 :5 EtOAc/petroleum ether) to give ethyl 2-fluoro-3,6-dimethoxybenzoate (8.1 g).

The synthetic route of 2-Fluoro-1,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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