Tag: M.W=100-200

Application of 4457-67-4, 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 4457-67-4 as follows.

b) 2-(4-Methoxybutoxy)-benzoic acid ethyl ester A solution of 4-methoxybutyl bromide (4.5 g) in acetonitrile (15 ml) is added dropwise under reflux to a mixture of salicylic acid ethyl ester (2.63 ml), powdered potassium carbonate (3.10 g) and potassium iodide (10 mg) in acetonitrile (50 ml), and the reaction mixture is then stirred overnight. After cooling, filtration is carried out, the filtrate is concentrated and the residue is added under a high vacuum. The title compound (4.4 g), Rf (C)=0.28, is obtained in the form of a pale-yellow oil.

According to the analysis of related databases, 4457-67-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba-Geigy Corporation; US5641778; (1997); A;,
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Related Products of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, molecular formula is C9H13NO, 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 5-Bromo-N- (4-ethoxybenzyl) -3-nitropyridin-2-amine (compound 62-2)[0000214] To a stirred solution of 2,5-dibromo-3- nitropyridine (1 g, 3.5 mmol, 1 equiv) in ethanol (10 mL) was added a (4-ethoxyphenyl)methanamine (580 IlL, 3.9 mmol, 1.1 equiv) and triethylamine (1 mL, 7.1 mmol, 2 equiv) . The reaction mixture was allowed to stir at room temperature for 18 hours, at which time LC-MS indicated the reaction was complete. The suspension was filtered and the solid washed with ethanol (2 x 5 mL) to produce compound 62-2 as a yellow solid (1.1 g, 92% yield)

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

Reference:
Patent; SIGA TECHNOLOGIES, INC.; DAI, Dongcheng; BURGESON, James, R.; AMBERG, Sean, M.; HRUBY, Dennis, E.; WO2013/123215; (2013); A2;,
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Electric Literature of 121588-79-2, 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. 121588-79-2, name is trans-4-Methoxycyclohexanamine, This compound has unique chemical properties. The synthetic route is as follows.

4-(4-fluoro-3-nitrophenyl)-3,5-dimethylisoxazole (0.609 g, 2.58 mmol) was dissolved in dry THF (20ml) and TEA (1.079 ml, 7.74 mmol). (lr,4r)-4-methoxycyclohexanamine (0.4 g, 3.10 mmol) was added and the reaction warmed to 60C and left to stir at rt for 84h. After cooling to rt the reaction mixture was poured into ice water (100ml), then extracted with ethyl acetate (2 x 100ml). Combined organics were concentrated in vacuo (azeotroping with acetonitrile) to afford the crude 4-(3,5-dimethylisoxazol-4-yl)- N-((lr,4r)-4-methoxycyclohexyl)-2-nitroaniline (1.1 g, 3.12 mmol, >100%), which was used without purification in the next step; Rt 2.40 min (method 1); m/z 346 (M+H)+

The chemical industry reduces the impact on the environment during synthesis trans-4-Methoxycyclohexanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; ONIONS, Stuart Thomas; TADDEI, David Michel Adrien; SHANNON, Jonathan; PAOLETTA, Silvia; BROWN, Richard James; SMYTH, Don; HARBOTTLE, Gareth; (376 pag.)WO2018/73586; (2018); A1;,
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Reference of 2338-54-7,Some common heterocyclic compound, 2338-54-7, name is 4-Fluoro-3-methylanisole, molecular formula is C8H9FO, 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 l-fluoro-4-methoxy-2-methylbenzene (2.0 g, 14.29 mmol) in CC , NBS (2.55 g, 14.29 mmol) and PI1CO3H (80 mg) were added. The reaction mixture was heated at reflux for 2 h, cooled to room temperature, and the solid was filtered off. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluting with PE/EA = 20/1) to give the target compound (3.0 g) as an oil. 1H NMR (CDC13): delta 6.97-6.83 (m, 3H), 4.48 (s, 2H), 3.78 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-3-methylanisole, its application will become more common.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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Synthetic Route of 106658-14-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 106658-14-4, name is 4-Methoxybenzene-1,2-diamine hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a. To a solution of 1,2-diamino-4-methoxybenzene hydrochloride (2 g) in acetonitrile (20 mL) was added dropwise tert-butylnitrite (1.35 mL) at 0 C. After 4 hours at room temperature, the mixture was concentrated under reduced pressure to a solid residue, which was then dissolved in water. The aqueous solution was neutralized with a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 5-methoxy-1H-benzotriazole as an off-white solid (1.2 g, 85%). MS (ES): M/Z [M+H]=150.

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

Reference:
Patent; AVENTIS AGRICULTURE; MERIAL LIMITED; Soll, Mark David; Le Hir de Fallois, Loic Patrick; Huber, Scot Kevin; Lee, Hyoung Ik; Wilkinson, Douglas Edward; Jacobs, Robert Toms; US2014/80862; (2014); A1;,
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These common heterocyclic compound, 106658-14-4, name is 4-Methoxybenzene-1,2-diamine hydrochloride, 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. Formula: C7H11ClN2O

Preparation 21 5-Methoxy-2-mercaptobenzimidazole Refer to Chart H (conversion of H-1 to H-2). To a magnetically stirred solution of 4-methoxy-o-phenylenediamine hydrochloride (20.0 g, 0.115 mol) in 400 ml of ethanol-water (4:1) is added 2 molar equivalent of 85% potassium hydroxide solution and 20 ml of carbon disulfide. The contents are warmed in a 75-80 C. oil bath for 2.5 hours and the solvent is removed in vacuo. To the residual thick slurry is added 200 ml of water, the contents heated to boiling, and 95% ethanol is added until a transparent solution is obtained. The solution is filtered, the filtrate is allowed to stand at 25 C. and the resulting cyrstalline solid is collected, and washed with water-ethanol. Drying in vacuo affords 11.0 g of the titled crystals mp 253-254.2 C. Concentration of the mother liquor and silica chromatography (280 g, acetone-methylene chloride, 1:6) gives an additional 3.9 g of product (total 14.9 g, 72% yield).

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

Reference:
Patent; The Upjohn Company; US5077407; (1991); A;,
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These common heterocyclic compound, 4132-48-3, name is 4-Isopropylanisole, 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 4-Isopropylanisole

Example 55; N-((1S, 2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6- isopropyl-3,4-dihydro-2H-chromen-4-yl] amino} propyl) acetamide; Step One; 6-isopropyl-2,3-dihydro-4H-chromen-4-one; A CH2C12 (350 ml) solution of 1-isopropyl-4-methoxy benzene (25 g, 166 mmol) and 3-chloro-propionly chloride (21 ml, 216 mmol), at r. t. , was treated with AlCl3 (33 g, 249 mmol) in 1-2 g portions over a 1 h period. Stirring was maintain at r. t. for 24 h at which time the mixture was poured onto crushed ice followed by the addition of 30 ml of conc. HC1. The mixture was diluted with 300 ml of CH2Cl2 and carefully washed (avoid emulsion) with 2 N NaOH. The organic layer was dried over MgSO4 and concentrated in vacuo a pale yellow oil. Flash chromatography (10% EtOAc/Heptanes) yields 6-isopropyl- 2,3-dihydro-4H-chromen-4-one (7.5 g, 24%).

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

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; PHARMACIA & UP JOHN COMPANY; WO2005/95326; (2005); 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. 2186-92-7, name is P-anisaldehyde dimethyl acetal, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2186-92-7

Phenyl 4,6-O-anisylidene-2,3-di-O-p-methoxybenzyl-1-thio-beta-D-glucopyranoside (3). To the solutionof 2 (20.0 g, 73.5 mmol) in the mixed solvent (CH3CN-DMF 735 mL:200 mL) were addedp-anisaldehyde dimethyl acetal (25.0 mL, 147 mmol) and (±)-camphor-10-sulfonic acid (CSA)(680 mg, 2.94 mmol) at 0 C. After stirring for 2.5 h at room temperature as the reaction wasmonitored by TLC (10:1 CHCl3-MeOH), the reaction was quenched by the addition of triethylamine.The reaction mixture was concentrated and diluted with EtOAc, of which solution was then added toseparatory funnel. After addition of distilled water to the solution, the desired 4,6-O-anisylidenatedproduct was appeared as a pure crystalline material (26.0 g, 91%), the physical data of which wasidentical to those reported in the literature [31]. To a solution of the 4,6-O-anisylidenated productobtained (2.00 g, 5.13 mmol) in DMF (25.7 mL) was added sodium hydride (492 mg, 20.5 mmol) at 0 C.After stirring for 1 h at 0 C, p-methoxybenzyl chloride (2.8 mL, 20.5 mmol) was added to themixture. After stirring for 17 h at rt as the reaction was monitored by TLC (1:2.5 EtOAc-n-hexane),the reaction was quenched by MeOH at 0 C. Dilution of the mixture with EtOAc provided a solution,which was then washed with H2O, satd aq NaHCO3 and brine. The organic layer was subsequentlydried over Na2SO4 and concentrated. The resulting residue was purified by silica gel columnchromatography (1:3 EtOAc-n-hexane) to give 3 (2.94 g, 91%). [alpha]D +3.3 (c 0.3, CHCl3); 1H-NMR(500 MHz, CDCl3) delta 7.54-6.82 (m, 17H, 4Ar), 5.54 (s, 1H, ArCH), 4.85 (d, 1H, Jgem = 10.9 Hz,ArCH2), 4.78-4.70 (m, 4H, ArCH2, H-1), 4.35 (dd, 1H, J5,6 = 5.2 Hz, Jgem = 10.3 Hz, H-6), 3.81-3.76(m, 11H, 3OCH3, H-3, H-6′), 3.66 (t, 1H, J3,4 = J4,5 = 9.5 Hz, H-4), 3.45 (m, 2H, H-2, H-5); 13C-NMR(125 MHz, CDCl3) delta 160.0, 159.4, 159.3, 133.1, 132.2, 130.5, 130.2, 129.9, 129.8, 129.0, 127.8,127.3, 113.8, 113.6, 101.1, 88.3, 82.7, 81.4, 80.1, 75.5, 74.9, 70.2, 68.6, 55.3, 55.2. HRMS (ESI) m/z:found [M+Na]+ 653.2180, C36H38O8S calcd for [M+Na]+ 653.2180.

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 2186-92-7.

Reference:
Article; Konishi, Miku; Imamura, Akihiro; Fujikawa, Kohki; Ando, Hiromune; Ishida, Hideharu; Kiso, Makoto; Molecules; vol. 18; 12; (2013); p. 15153 – 15181;,
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121588-79-2, name is trans-4-Methoxycyclohexanamine, 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: C7H15NO

Example 625: (2R)-2-[6-(5-chloro-2-{[trans-4-methoxycyclohexyl]amino}pyrimidin-4-yl)-1 – oxo-2,3-dihydro-1 H-isoindol-2-y l]-N-[(1 S)-2-hydroxy-1 -(3- methoxyphenyl)ethyl]propanamide (3479) (3480) A mixture of (R)-2-(6-(2,5-dichloropyrimidin-4-yl)-1-oxoisoindolin-2-yl)-N-((S)-2-hydroxy-1-(3- methoxyphenyl)ethyl)propanamide (Preparation 352, 0.1 g, 0.199 mmol), DIPEA (0.070 ml, 0.399 mmol) and trans 4-methoxycyclohexanamine (0.039 g, 0.299 mmol) (0.024 ml, 0.232 mmol) in 1 :1 EtOH:dioxane (1 mL) was heated at 80C under nitrogen overnight. The mixture was allowed to cool to room temperature and was concentrated under vacuum. The residue was dissolved in EtOAc and transferred into a separating funnel. 1 N HCI was added and the crude product was extracted with EtOAc. The combined organic extracts were washed with NaHC03, brine, dried (MgS04) and absorbed on silica. The crude product was purified by chromatography on the Companion (12 g column, 0- 5 % MeOH in DCM) to afford the title compound (0.06g, 050.1 %) as a white solid after trituration and evaporation from Et.20. 1 H NMR (DMSO-d6) delta: 8.56 (d, 1 H), 8.44 (s (br), 1 H), 8.07 – 8.01 (m, 1 H), 7.97 (d, 1 H), 7.75 (d, 1 H), 7.52 (s (br), 1 H), 7.28 – 7.19 (m, 1 H), 6.93 – 6.85 (m, 2H), 6.83 – 6.76 (m, 1 H), 5.06 – 4.96 (m, 1 H), 4.89 (t, 1 H), 4.85 – 4.80 (m, 1 H), 4.77 (d, 1 H), 4.60 (d, 1 H), 3.75 (s, 3H), 3.73 – 3.63 (m, 1 H), 3.57 – 3.52 (m, 2H), 3.23 (s, 3H), 3.16 – 3.06 (m, 1 H), 2.05 – 1.91 (m, 4H), 1.45 (d, 3H), 1.39 – 1.13 (m, 4H). LCMS: [M+H]+ = 594.

The synthetic route of 121588-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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Application of 4132-48-3,Some common heterocyclic compound, 4132-48-3, name is 4-Isopropylanisole, molecular formula is C10H14O, 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 CH2CI2 (350 mL) solution of 1-isopropyl-4-methoxy benzene (25 g, 166 mmol) and 3-chloro-propionyl chloride (21 mL, 216 mmol), at room temperature, was treated with AIC13 (33 g, 249 mmol) in 1-2 g portions over a 1 h period. Stirring was maintained at room temperature for 24 h, then the mixture was poured onto crushed ice, and then conc. HCI (30 mL) was added. The mixture was diluted with CH2CI2 (300 mL), washed with 2 N NaOH, dried (magnesium sulfate), and concentrated in vacuo a pale yellow oil. Flash chromatography (10% EtOAc/Heptanes) yields 6-isopropyl-2, 3- dihydro-4H-chromen-4-one (7.5 g, 24%). Rf = 0.3. HRMS (ESI+) calc’d for C12Hl4O2 mlz 191. 1072 [M+H] + ; found 191.1071.

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

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87714; (2005); A2;,
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