Tag: M.W=100-200

Application of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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 stirred mixture of 2,2-diethoxy-IV,JV-dimemylcthanapiiine (15.7 g, 97.5 mmol) and water (16.4 mL) at room temperature under a nitrogen atmosphere was added aq. 37percent HCl (16.4 mL, 195 mmol). After addition the mixture was stirred at 40°C (bath) for 25 hours. It was then cooled to 0 °C (bath) to give Solution A. KOH (14.0 g, 250 mmol) was dissolved in water (75 mL) at room temperature under a nitrogen atmosphere. It was then cooled to 0 °C (bath) to give Solution B. To a stirred heterogeneous mixture of compound 160 (19.97 g, 39.0 mmol) at room temperature under a nitrogen atmosphere was added a rninirnurn amount of DMA (60 mL) to give a homogeneous solution. LiCl (1.65 g, 39.0 mmol) was then added and the resulting mixture was stirred atO °C (bath) for 15 min. The cold Solution B was then added and the reaction was stirred at 0 °C for 2 min. Cold Solution A was then added and the final reaction mixture was stirred further at 0 °C under a nitrogen atmosphere. The reaction was monitored by TLC (DCM/MeOH=10:l). After 30 min more KOH (s) (5.0 g, 89 mmol) was added and the reaction was stirred further at 0 °C for 1.5 hours. It was then poured into water (1,000 mL). Petroleum ether (1,000 mL) was added and the mixture was stirred at room temperature for 20 min. The petroleum ether layer was decanted before more petroleum ether (600 mL) was added and the mixture was again stirred for 15 min. The solid was collected by filtration, washed with water (5×200 mL) and dried under reduced pressure over silica gel/KOH to give (2J3)-iV-[4-(3-bromo-4-fluoroanilino)pyrido[3,4-Lambda(|pyrimidin-6-yl]-4- (dimethykmino)-2-butenamide (161) (16.9 g, 97percent).

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-Diethoxy-N,N-dimethylethanamine, its application will become more common.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; SMAILL, Jeffrey, Bruce; PATTERSON, Adam Vorn; DENNY, William, Alexander; WILSON, William Robert; LU, Guo-Liang; ANDERSON, Robert, Forbes; LEE, Ho Huat; ASHOORZADEN, Amir; WO2010/104406; (2010); 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 450-91-9 as follows. Safety of 4-Fluoro-2-methoxyaniline

In a flask equipped with a water cooled condenser a phenyl amine (1.0 equiv.), bis(2- chloroethyl)amine hydrochloride (1.5 equiv.), potassium carbonate (1.5 equiv.) and sodium iodide (0.4 equiv.) were suspended in diglyme. The resulting reaction mixture was allowed to heat to reflux over a period of one hour and allowed to stir at reflux for an additional 2.5 hours. It was then partitioned between dichloromethane and distilled water. The pH of the water layer was adjusted to basic pH (9-10) with 5% aqueous sodium hydroxide. The water phase was extracted thrice with dichloromethane. The combined organic layers were washed once with 10% aqueous sodium thiosulfate to remove iodine, dried over anhydrous sodium sulfate and the solvent removed in vacuo. The product was purified by column chromatography in 2M ammonium/methanol and dichloromethane mixtures.; l-(4-Fluoro-2-methoxy-phenyl)-piperazine was synthesized from 4-Fluoro-2-methoxy- phenylamine (151.5 mg, 1.07 mmol), bis(2-chloroethyl)amine hydrochloride (287.4 mg, 1.61 mmol), potassium carbonate (222.5 mg, 1.61 mmol) and sodium iodide (64.5 mg, 0.43 mmol) in diglyme. Column chromatography 10% 2M ammonia/methanol in dichloromethane provided the product as a dark brown oil (89.8mg, 40%). 1H NMR (300 MHz, CDCl3): delta(ppm) 6.78-6.90(m, IH), 6.57-6.65(m, 2H), 3.86(s, 3H), 3.14(broad t, 2H), 3.05(broad t, 4H), 2.95(t, IH), 2.72(broad t, 2H).

According to the analysis of related databases, 450-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/71730; (2006); A1;,
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Application of 111-95-5,Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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 mixture of 3,6-diaminopyrazine-2,5-dicarboxylic acid (200 mg, 1.01 mmol), bis-2- (methoxyethyl)amine (372 mul_, 335.5 mg, 2.52 mmol), HOBt-H2O (459 mg, 3.00 mmol), and EDC-HCI (575 mg, 3.00 mmol) were stirred together in DMF (20 m._) for 1 h at room temperature. The mixture was concentrated to dryness and the residue was partitioned withEtOAc and water. The layers were separated and the EtOAc solution was washed with saturated NaHCO3 and brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated. Purification by radial flash chromatography (SiO2, 10/1 CHCI3-MeOH) afforded 228.7 mg (53% yield) of Example 1 as an orange foam: 1H NMR (300MHz, CDCI3), delta 4.92 (s, 4 H), 3.76 (apparent t, J = 5.4 Hz, 4 H), 3.70 (apparent t, J = 5.6 Hz, 4 H), 3.64 (apparent t, J = 5.4 Hz, 4 H)1 3.565 (apparent t, J = 5.4 Hz), 3.67 (s, 6 H), 3.28 (s, 6 H). 13C NMR (75 MHz, CDCI3) delta 167.6 (s), 145.6 (s), 131.0 (s), 72.0 (t), 70.8 (t), 59.2 (q), 49.7 (t), 47.1 (t). LCMS (5- 95% gradient acetonitrile in 0.1 % TFA over 10 min), single peak retention time = 3.14 min on 30 mm column, (M+H)+ = 429. UV/vis (100 muM in PBS) lambdaabs = 394 nm. Fluorescence (100 nm) lambdaex = 394 nm.lambdaem = 550 nm.

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MALLINCKRODT INC.; WO2007/149479; (2007); A1;,
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37466-89-0, name is 3-Methoxybenzene-1,2-diamine, 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. SDS of cas: 37466-89-0

A solution of 2,3-diaminoanisole (400 mg, 2.89 mmol) and chloroacetic acid (557 mg, 6 mmol) in 4 N HCl was heated to 105 C. for 16 hours. The mixture was then cooled, neutralized (to a pH of 8) with aqueous sodium bicarbonate, and extracted twice with dichloromethane. The organic fractions were then dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel flash chromatography using a 1:1 mixture of hexanes:ethyl acetate as an eluent to give 1H-2-chloromethyl-4-methoxybenzimidazole as a yellow foam in a yield of 386 mg (68%). 1H NMR (CDCl3) delta 3.96 (s, 3H), 4.85 (s, 2H), 6.71 (m, 1H), 7.19 (m, 2H).

The synthetic route of 37466-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bridger, Gary; Kaller, Al; Harwig, Curtis; Skerlj, Renato; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; McEachern, Ernest J.; Atsma, Bem; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher D.; Di Fluri, Maria R.; US2004/19058; (2004); A1;,
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Related Products of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, 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.

Example 6 To a mixture of 16.6 g of compound according to example 2 in toluene (600 ml) trimethyi ortobenzoate (120 ml) and camphenesulphonic acid (4 g) were added. The mixture was stirred vigorously at rt for 3 h, then 80 % acetic acid (160 ml) was added. After further 1 h of stirring the biphasic mixture obtained was separated, the organic phase was diluted with toluene (600 ml), washed with water (800 ml) and sat. NaHC03 (2 x 600 ml), dried, filtered and evaporated. The resulting oil was dropped into 600 ml of heptane and seeded. The white crystalline compound was filtered, washed and dried to yield 1 10.3 g of acceptor (a compound of general formula 6, wherein R|= Bn, R2= 4-chlorobenzoyl, R3= benzoyl, ORj in beta). [a]D = +17.13 (c = 1 DCM), Mp 156-157 C.

Statistics shows that (Trimethoxymethyl)benzene is playing an increasingly important role. we look forward to future research findings about 707-07-3.

Reference:
Patent; GLYCOM A/S; BAJZA, Istvan; DEKANY, Gyula; AGOSTON, Karoly; PEREZ, Ignacio Figueroa; BOUTET, Julien; HEDEROS, Markus; HORVATH, Ferenc; KOVACS-PENZES, Piroska; KROeGER, Lars; ROeHRIG, Christoph; SCHROVEN, Andreas; VRASIDAS, Ioannis; TRINKA, Peter; KALMAR, Laszlo; KOVACS, Imre; DEMKO, Sandor; AGOSTON, Agnes; RISINGER, Christian; WO2011/100980; (2011); A1;,
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Application of 767-91-9, 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. 767-91-9, name is 2′-Methoxyphenyl acetylene, This compound has unique chemical properties. The synthetic route is as follows.

Cuprous iodide (9.5 mg, 0.05 mmol) was weighed out,Sodium carbonate (530 mg, 5 mmol),Tetrabutylammonium nitrite (288 mg, 1 mmol) and 2-methoxyphenylacetylene (132 mg, 1 mmol) were sequentially added into a 25 mL reaction vessel and the mixture was purged with nitrogen three times. Purified THF (4.0 mL), charged with CO2 (0.1MPa). Closed reactor, placed in a 25 C oil bath reaction 16h, after the reaction, open the valve on the reactor slowly release the remaining gas, and then the reaction vessel was transferred to a single port flask to concentrate, and with 5mL of deionized water Diluted and then extracted with n-hexane. The aqueous layer was acidified to pH = 1 at low temperature by addition of 1 M hydrochloric acid and extracted with ether. The organic phase was collected, washed with brine, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo. 2-Methoxyphenylacetophenic acid was obtained in a yield of 83%.

The chemical industry reduces the impact on the environment during synthesis 2′-Methoxyphenyl acetylene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dalian University of Technology; Feng Xiujuan; Jia Lihong; Bao Ming; (19 pag.)CN107353194; (2017); A;,
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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. 645-36-3, name is 2,2-Diethoxyethanamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

1.5 g of 2-piperidone was dissolved in 75 mL of mesitylene, 248 muL of titanium tetrachloride was added thereto, and heated at 140C. A solution obtained by dissolving 4.02 g of aminoacetoaldehyde diethyl acetal to 45 mL of mesitylene was prepared, and was added dropwise to the previous mesitylene solution over 3 hours. The mixture was stirred at 140C for 70 hours, then cooled back to room temperature, and was extracted with a 2N aqueous solution of hydrochloric acid. The obtained aqueous layer was basified with a 5N aqueous solution of sodium hydroxide, and then was extracted with chloroform. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the purification was carried out by distillation under reduced pressure (3mmHg, 120C), to obtain 375 mg of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [44-1] as a pale yellow oily product.

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; BANYU PHARMACEUTICAL CO., LTD.; EP1790650; (2007); A1;,
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Reference of 22236-10-8,Some common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.09 g, 4.21 mmol) prepared as described above (Intermediate 2, 1.0 g, 3.86mmol) was dissolved in anhydrous acetonitrile (3 mL) and 4-difluoromethoxyaniline was added (1.34 g, 8.42 mmol). The mixture was heated at 180 C. for 600 s in a microwave (Emrys Optimizer model, Personal Chemistry). The solvents were removed under vacuum to give the desired product as a beige powder (1.3 g, 94.2%). The crude product was used for the subsequent step.

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

Reference:
Patent; Kelly, Michael G.; Kincaid, John; Kaub, Carl J.; US2006/258689; (2006); A1;,
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Application of 450-91-9, These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, 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.

To a solution of EDCI?HCl (573.2 mg, 2.99 mmol) in DMF (7 mL) and CH2Cl2 (7 mL) were successively added OxymaPure® (425.0 mg, 2.99 mmol) and S1 (1.00 g, 2.72 mmol) at room temperature. After stirring the reaction mixture for 5 min, 4-fluoro-2-methoxyaniline (470.6 mg, 2.99 mmol) dissolved in DMF (1 mL) and DIPEA (590 muL, 4.08 mmol) were added, the reaction mixture was stirred at the same temperature for 11 h. The volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and 1 N HCl aq. was added. The resulting mixture was extracted with ethyl acetate twice, the combined organic layers were washed with aqueous saturated NaHCO3 twice, H2O, brine and dried over Na2SO4. After filtration, the residue was concentrated under reduced pressure and dried in vacuo to give crude amide as brown solid. To the amide in DMF (9 mL) was added piperidine (240 muL, 4.08 mmol) and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate and H2O was added. The resulting mixture was extracted with ethyl acetate twice, the combined organic layers were washed with H2O, brine, dried over Na2SO4. Filtrate was concentrated and the resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane = 12/88 to 100/0) to give S2 (464.9 mg, 1.73 mmol, 64percent over 2 steps) as a pale brown oil.Pale brown oil; [alpha]D27 ?6.1 (c 0.44, CH3OH); 1H NMR (400 MHz, CD3OD) delta 8.01 (dd, J = 8.8 , 6.2 Hz, 1H), 6.84 (dd, J = 10.5, 2.7 Hz, 1H), 6.66 (ddd, J = 8.8, 8.6, 2.7 Hz, 1H), 3.89 (s, 3H), 3.46 (dd, J = 7.3, 5.6 Hz, 1H), 1.86?1.77 (m, 1H), 1.66?1.53 (m, 2H), 1.35?1.29 (m, 2H), 0.93 (d, J = 6.6 Hz, 3H), 0.92 (d, J = 6.6 Hz, 3H); 13C NMR (100 MHz, CD3OD) delta 176.3, 161.4 (d, J = 240.6 Hz), 152.7 (d, J = 10.2 Hz), 124.3 (d, J = 3.6 Hz), 123.4 (d, J = 9.5 Hz), 107.1 (d, J = 21.9 Hz), 100.2 (d, J = 27.0 Hz), 56.9, 56.6, 35.8, 34.2, 29.2, 23.0, 22.9; 19F NMR (376 MHz, CD3OD) delta ?117.4; IR (neat) nu 3019, 2959, 1673, 1611, 1531, 1465, 1415, 1216, 757, 669 cm?1; HRMS (ESI) calcd. for C14H22N2O2F m/z 269.1660 [M+H]+, found 269.1651.

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nonoyama, Akihito; Kumagai, Naoya; Shibasaki, Masakatsu; Tetrahedron; vol. 73; 11; (2017); p. 1517 – 1521;,
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Related Products of 148583-65-7, A common heterocyclic compound, 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, molecular formula is C9H12FNO, 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.

Example 18(6-Bromo-5-methyl-thieno[2,3-c lpyrimidin-4-yl)-(4-fluoro-2-isopropoxy-phA mixture of 6-bromo-4-chloro-5-methyl-thieno[2,3-c/]pyrimidine (456 mg), 4-fluoro-2- isopropoxy-phenylamine (293 mg) and p-toluenesulfonic acid (33 mg) in dioxane (6 ml) was stirred at 80C for three days. The reaction mixture was quenched withEtOAc and 10% aq. K2CO3 and filtered. The residue was washed with further EtOAc and dried to yield the title compound.Yield: 288 mgESI mass spectrum: m/z = 397 (M+H)+ 1 H NMR (400MHZ; d6DMSO; 20C): delta 8.47 (s, 2H), 8.34 (s, 1 H), 7.1 7-7.03 (m, 1 H),6.90-6.78 (m, 1 H), 4.88-4.76 (m, 1 H), 2.74 (s, 3H), 1 .35 (d, 6H).

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; HIMMELSBACH, Frank; LEHMANN-LINTZ, Thorsten; REDEMANN, Norbert; SAUER, Achim; THOMAS, Leo; BLACK, Phillip; BLACKABY, Wesley; DANILEWICZ, John; LINNEY, Ian; AUSTEN, Matthias; SCHNEIDER, Martin; SCHREITER, Kay; WO2011/104338; (2011); A1;,
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