Tag: M.W=100-200

Application of 7252-83-7, 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 7252-83-7 as follows.

Step 1: Methyl 2-bromo-3-cyclohexyl-l-(2.2-dimethoxyethyl)-lH-indole-6-carboxylate; To a stirred solution of methyl 2-bromo-3-cyclohexyl-lH-indole-6-carboxylate (prepared as described in published International patent application WO2004/087714) (0.2 M, 1 eq.) in DMF at RT was added NaH (60 % dispersion in mineral oil, 1.75 eq). After Ih, KI (8 mol %) and bromoacetaldehyde dimethyl acetal (2.5 eq) were added and the reaction heated at 80 0C for 17 h. After cooling to RT, the reaction was quenched by addition of aqueous HCl (IN) and extracted into EtOAc (x3). The combined organics were washed with HCl (IN), H2O and brine before being dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (Biotage, 5-10 % EtOAc/PE gradient) gave the title compound as a white solid (79 %); MS (ES+) m/z 446 (M+H)+, 448 (M+H)+.

According to the analysis of related databases, 7252-83-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); A2;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 366-99-4

General procedure: To a solution of compound 12 (bakuchiol-o-triflate) (1 mmol) in toluene (10 mL M), amine (3.0 mmol), Cs2CO3 (4.0 mmol), ligand (±) BINAP (0.6 mol) and Pd(OAc)2 (0.2 mol) were added under an inert atmosphere. The reaction mixture was degassed at RT and refluxed (120 °C) for 24 hr. Then, the reaction mixture was brought to RT, diluted with EtOAc and filtered through celite. To the reaction mixture, brine (20 mL) was added and extracted with EtOAc (2 × 10 mL). The combined organic layerwas dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the product after silicagel chromatography purification (Hex/EtOAc, 9.5:0.5).

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 366-99-4.

Reference:
Article; Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 75 – 80;,
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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. 16452-01-0, name is 3-Methoxy-4-methylaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Step 1: 4-Methyl-3-methoxyphenyl hydrazine. The compound was prepared by a method analogous to that of Example 22, Step 1. The reaction of 100 g (0.73 mole) of 4-methyl-3-methoxyaniline and 50.5 g (0.73 mole) of sodium nitrite in the presence of 330 g (1.46 moles) of stannous chloride dihydrate, 1160 mL of concentrated hydrochloric acid and 250 mL of water gave 58.0 g of product as an 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; FMC Corporation; US4702763; (1987); A;,
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Electric Literature of 36865-41-5, 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 36865-41-5 as follows.

A mixture of 327 mg (2.00 mmole) OF 7-HYDROXY-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (prepared as detailed in WO 01/77100 utilizing 3-aminophenol in place of 4-aminophenol) and 415 mg (3.0 mmole) of potassium carbonate in 8 ML of CH3CN was heated at reflux for 22 hr. After cooling to room temperature, the mixture was diluted with EtOAc, filtered through celite, and concentrated. Purification by flash column chromatography (SiO2, 20% EtOAc/hexanes gradient to 70% ETOAC/HEXANES) GAVE 380 mg (75%) of 7-BENZYLOXY-3, 4-DIHYDRO-1H-QUINOLIN- 2-one as a white solid. MS : M/Z 254.1 (M+1) 7-BENZYLOXY-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (379 mg, 1.50 mmole) was dissolved in 8 ML of anhydrous DMF under a N2 atmosphere and cooled in an ice bath. NaH (57 mg, 2.24 mmole) was added in a single portion, and the resulting gray suspension was stirred at 0 C for 10 min. 3-BROMO-L-METHOXYPROPANE (275 mg, 1. 8 mmole) was added, and the reaction mixture was stirred at room temperature for 3 hr. Excess hydride was quenched by the addition of a large excess of H2O, and the aqueous layer was extracted with EtOAc (3x). The combined organic layers were washed with H20 (2X) and brine, dried over MGS04, filtered, and concentrated. Purification by flash column chromatography (SIO2, 10% EtOAc/hexanes gradient to 40% ETOAC/HEXANES) provided 382 mg (78%) of 7-BENZYLOXY-L- (3-METHOXYPROPYL)- 3, 4-DIHYDRO-LH-QUINOLIN-2-ONE as a clear viscous oil. MS : M/Z 326.1 (M+1) 7-BENZYLOXY-1- (3-METHOXYPROPYL)-3, 4-DIHYDRO-LH-QUINOLIN-2-ONE (355 mg, 1.09 mmole) was dissolved in 50 mL of MEOH and hydrogenated over 0.1 g of 20% Pd/C at 50 psi for 16 hr. The catalyst was removed by filtration through celite, and the solution was concentrated to dryness to afford 259 mg (100%) of 7-HYDROXY-L- (3-METHOXYPROPYL)-3, 4- DIHYDRO-LH-QUINOLIN-2-ONE as a light brown viscous oil which was used without further purification. MS: NIEZ 236. 1 (M+1)

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/89915; (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. 1758-46-9, name is 2-Phenoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Phenoxyethylamine

An oven-dried vial was subsequently charged with 0.1 eq. of a palladium source [Pd], 0.2 eq. (biph)P(betau)2, 1.0 eq. arylhalide B with X = -O-Benzyl, -O-Methyl, -CN or – C(=O)-OCH3 and 1.4 eq. base. The vial was evacuated and purged with argon, and the respective amine HNR1R2 (1.3 eq.) was added. The solvent was added to obtain a concentration of 1.0 M of the arylhalide B. The vial was sealed and heated to either 1000C in case of toluene as the solvent or 110°C in case of DME as the solvent in each case for 22 h. EPO The reaction mixture was transferred into a flask using H2O and MeOH and the total volume was reduced to less than 10 mL Purification was achieved by prep. HPLC. In order to remove any ammonium formate derivative formed during preparative HPLC, the resulting product was taken up in chloroform, extracted twice with saturated aq. NaHCO3, the combined aq. phases were re-extracted with chloroform, and the combined organic phases were dried over MgSO4. If any additional workup was applied, this is indicated in the table 1.

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 1758-46-9.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; WO2006/69807; (2006); A1;,
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Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, 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. Formula: C7H7F3N2O

2-Hydroxymethyl- and 2-ethyl-5-trifluoromethoxybenzimidazole. The procedure of Philips, M. A. was used. A mixture of 2-amino-4-trifluoromethoxyaniline (0.7 g, 0.0036 Mol) and corresponding carboxylic acid (0.00546 Mol) in HCl (3.5 ml, 4N) was refluxed for 6 h. Water (5 mL), and 0.5 g of charcoal were added, and the mixture was refluxed 10-15 min. After cooling, the mixture was filtered and resulted clear filtrate was washed with ether (2×10 mL). The water layer was neutralized with excess of diluted NH4OH, the precipitate was filtered, washed with water, and dried.2-Hydroxymethyl-5-trifluoromethoxybenzimidazole. Glycolic acid was used, R(HO)CH2. Yield 0.65 g (75 wt. %). M.p. 192-194 C. 1H NMR (DMSO-d6): 4.68 (d, 5.5 Hz, 2H), 5.67 (t, 5.5 Hz, 2H), 7.05 (d, J=8.0 Hz, 1H), 7.38 (s, 1H), 7.49 (br s, 1H), 12.48 (br s, 1H). 13C NMR (DMSO-d6): 57.62, 104.44, 110.79, 111.98, 114.70, 118.20, 120.08 (q, J=254.8 Hz), 143.21, 157.22. 19F NMR (DMSO-d6): -57.76. [M+1]+ 233.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 658-89-9, its application will become more common.

Reference:
Patent; The United States of America as represented by the United States Department of Energy; US8242284; (2012); B1;,
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Application of 3616-56-6, A common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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 43 N,N-Diethyl-5-[[2-(dimethylamino)ethyl]amino]-2H-[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine A mixture of 5.0 g (0.015 mol) of 5-amino-N,N-diethyl-2H[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine, 2.4 g (0.015 mol) of 2,2-diethoxy-N,N-dimethyl ethanamine, and 0.001 g of p-toluenesulfonic acid in 100 ml of 2-propanol was heated under reflux for four hours, allowed to cool to room temperature, and treated portionwise with 1.0 g (0.026 mol) of NaBH4 over a two hour period. The mixture was stirred at room temperature for 16 hours and poured into 1 l of H2 O. The precipitate that formed was collected, washed with H2 O, dried, and recrystallized to give the product. An example of another 5-(monoalkylated or acylated)-2-(substituted)benzothiopyrano[4,3,2-cd]-indazole, prepared in the manner of Examples 5-11, is as follows: N-[2-[2-(diethylamino)ethyl]-2H[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]-1,3-propanediamine, hydrochloride salt, mp 222° C. dec.

The synthetic route of 3616-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4604390; (1986); A;,
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38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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. HPLC of Formula: C9H13NO

A mixture of e-1 (0.0037 mol) and e-2 (0.0151 mol) was stirred at 60C for 2 hours, then purified by column chromatography over silica gel (eluent: CH2CyCH3OH (98/2); 15mum). The pure fractions were collected and the solvent was evaporated. Yield: 1 g of intermediate e-3 (100%).

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136561; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 24599-58-4, name is 2,5-Dimethoxytoluene, 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 24599-58-4, Computed Properties of C9H12O2

Preparation of 2,5-dimethoxy-4-methylacetophenone. 1 mol (152 g) of 2,5-dimethoxytoluene is introduced, whilst stirring, into 230 ml of acetyl chloride at -10 C. 160 g of aluminium chloride are then added in the course of 3 hours, whilst stirring and keeping the temperature of the reaction medium at between -10 and 0 C. When the addition has ended, the mixture is stirred for a further 3 hours at between -10 and 0 C. The reaction medium is then poured onto 1 kg of crushed ice to which 110 ml of hydrochloric acid (d=1.19) have been added. After a few hours, the reaction product which has precipitated is filtered off. After washing with water, a 2 N solution of sodium hydroxide and then again with water, the 2,5-dimethoxy-4-methylacetophenone is recrystallized from ethanol. After drying in vacuo, it melts at 75 C.

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; Bugaut; Andree; Grollier; Jean-Francois; Vandenboosche; Jean-Jacques; US4185958; (1980); 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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, A new synthetic method of this compound is introduced below., name: 1-Bromo-2,2-dimethoxypropane

The thioamide from above (0.36 g, 1.63 mmol, 1.0 eq) was suspended in EtOH (10 mL, absolute) under argon at rt. 1-Bromo-2,2-dimethoxypropane (0.22 mL, 1.63 mmol, 1.0 eq) was added via syringe and stirring continued for 72 h at rt. The mixture was then heated to 70 C. for 16 h and concentrated in vacuo. Mass spectrometric analysis of the crude residue was consistent with a corresponding thiazole structure, and no further manipulation was performed before removal of the Boc protecting group in the next step. ESI-MS (m/z) 257 [M+H]+, 201 [M-tBu]+, 157 [M-Boc]+.

The synthetic route of 126-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Erickson, Shawn David; Baldwin, John J.; Dolle III, Roland Ellwood; Inglese, James; Ohlmeyer, Michael H.J.; Ho, Koc-Kan; Bohnstedt, Adolph C.; Kultgen, Steven G.; Conti, Paolo Giovanni Martino; Leysen, Dirk; van der Louw, Jaap; US2004/87601; (2004); A1;,
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