Tag: M.W=100-200

Some common heterocyclic compound, 142166-01-6, name is Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate, molecular formula is C10H11NO3, 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 C10H11NO3

Step 3: 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (1 g, 5.2 mmol) was dissolved in MeOH (5 ml) and THF (10 ml) in a 25 mL flask, to which LiOH (2 g) dissolved in H2O (5 ml) was added, followed by stirring at room temperature for 12 hours. Upon completion of the reaction, the solvent was concentrated. The pH of the reaction mixture was adjusted to 5 by using 2N HCl. The mixture was extracted with EA. The organic layer was dried over MgSO4 and filtered. As a result, 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid was obtained (1.2 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 142166-01-6, its application will become more common.

Reference:
Patent; Hyundai Pharm Co., Ltd.; LEE, In Hee; CHAE, Hee Il; KIM, Se hoan; MOON, Soon Young; HA, Tae Young; CHOI, Hyo sun; KIM, Young Seok; KIM, Chun hwa; RHEE, Jae Keol; (132 pag.)US2016/355483; (2016); 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 35180-01-9 as follows. Recommanded Product: Chloromethyl isopropyl carbonate

Step 1. Preparation of Iodomethylisopropyl carbonate: Tea solution of anhydrous sodium iodide (6 g, 40 mmol) in anhydrous acetonitrile (20 mL) chloromethyl isopropyl carbonate (2.9 g, 19 mmol) in anhydrous, acetonitrile (10 mL) was added drop wise over 20 min. The reaction mixture, covered with aluminum foil (protected from light) was stirred at room temperature overnight. The solid separated was filtered, washed with acetonitrile and the filtrate was concentrated under reduced pressure. Residue was dissolved in water (10 mL) and organics were extracted in ether (25 mL). Ether extracts were washed with sodium bisulfite (5%, 10 mL), later brine (10 mL). Organic layer was dried over anhydrous, sodium, sulfate, filtered, concentrated and dried under high dried vacuum. Yield 2.72 g (58%); 1H-NMR delta 1.3 (d, 6H), 4.95 (m, 1H), 5.95 (s, 2H).

According to the analysis of related databases, 35180-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPRING BANK PHARMACEUTICALS, INC.; Iyer, Radhakrishnan P.; Coughlin, John Edward; (35 pag.)US2015/329864; (2015); A1;,
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Application of 37466-90-3, 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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of ethyl 3,4-diaminobenzoate 19 (1 eq., 27.7 mmol) and appropriate benzoic acid (1 eq.,27.7 mmol) and 20 mL of polyphosphoric acid was heated at 140 C for 3 h. Warm reaction mixture was poured onto ice covered with excess of solid NaHCO3 and then 60 mL of AcOEt were added. Aqueous phase was extracted with AcOEt (4×70 mL). Extracts were dried over Na2SO4 and concentrated. The crude product was purified by chromatography on silica gel (eluent heptane/AcOEt, 0-60 % or CHCl3/MeOH 0-5 %).

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,4-diaminobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Moszczy?ski-P?tkowski, Rafa?; Majer, Jakub; Borkowska, Ma?gorzata; Bojarski, ?ukasz; Janowska, Sylwia; Mat?oka, Miko?aj; Stefaniak, Filip; Smuga, Damian; Bazyd?o, Katarzyna; Dubiel, Krzysztof; Wieczorek, Maciej; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 96 – 116;,
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Synthetic Route of 335599-07-0,Some common heterocyclic compound, 335599-07-0, name is Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate, molecular formula is C8H12O3, 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.

(3-Oxa-bicyclo[3.1.0]hex-6-yl)-methanol (56)-A 1M solution of LiAlH4 in THF (16.77 mL, 16.77 mmol) was cooled in an ice-water/acetone bath and a solution of 56 (2.62 g, 16.77 mmol) in THF (25 mL) was added slowly with stirring. The reaction was warmed to RT over 30 min and stirred for 1 h. The reaction was quenched by slow portionwise addition of 4.8 g of Na2SO4.10H2O, Stirring was continued for additional 1 h after the vigorous reaction subsided. MgSO4 was added and solids were removed by filtration, rinsed with fresh THF and solvents evaporated. The residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 50% EtOAc) to afford 0.98 g (51.3%) of 56 as a colorless liquid.

The synthetic route of 335599-07-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); 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. 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H12N2O2

Methyl 3-amino-4-(methylamino)benzoate (0.49 g, 2.75 mmol) in DMF (5 ml) was added to a solution of 4-benzyloxybenzoic acid (0.62 g, 2.75 mmol) in DMF (4 ml) at 0 C. Subsequently, HOAt (0.4 g, 3.0 mmol) and WSCI-HCl (0.58 g, 3.0 mmol) were added to the former solution at 0 C and stirred at 20 C for 15 h. The reaction mixture was quenched with sat. NH4Cl and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by the silica gel column chromatography to give 2-1 in 58% yield.

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 66315-16-0.

Reference:
Article; Fujimori, Ko; Iguchi, Yusuke; Yamashita, Yukiko; Gohda, Keigo; Teno, Naoki; Molecules; vol. 24; 22; (2019);,
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Reference of 83881-47-4, These common heterocyclic compound, 83881-47-4, name is Methyl 2-(2-chloroethoxy)acetate, 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.

Alkylation of 2-Fluoro-5-nitro-phenylamine with (2-Chloro-ethoxy)-acetic acid methyl ester in an inert solvent in the presence of base will give [2-(2-Fluoro-5-nitro-phenylamino)-ethoxy]-acetic acid methyl ester.

The synthetic route of 83881-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Drug Innovation & Design, Inc.; US2003/138432; (2003); A1;,
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Some common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, molecular formula is C7H12O3, 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. Application In Synthesis of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

In a three-necked flask fitted with thermometer, dropping funnel and gas exhaust, 7.39 g (58.19 mmol) of oxalyl chloride were initially charged in 116 ml of abs. dichloromethane at -78 C. 9.08 g (116.38 mmol) of dimethyl sulphoxide, dissolved in 8 ml of abs. dichloromethane, were then slowly added dropwise (careful: intensive evolution of gas), with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 5 min 7.63 g (52.90 mmol) of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (described in M. H. Parker et al. U.S. Pat. Appl. Publ., 20120053146), dissolved in 196 ml of abs. dichloromethane, were then slowly added dropwise, with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 10 min 26.72 g (264.51 mmol) of triethylamine were then slowly added dropwise, with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 10 min and then warmed to RT over 2 h. The mixture was diluted with 700 ml of methyl tert-butyl ether, the precipitate was filtered off and the filtrate was concentrated at 30 C. and 100 mbar. The residue was purified by flash chromatography (mobile phase: dichloromethane). This gave 7.30 g (97% of theory, purity about 95% according to NMR) of the title compound. (0307) 1H NMR (500 MHz, CDCl3): delta [ppm]=1.32 (t, 3H), 1.58-1.63 (m, 2H), 1.65-1.70 (m, 2H), 4.28 (q, 2H), 10.41 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3697-68-5, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (46 pag.)US2016/145271; (2016); A1;,
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Synthetic Route of 10259-22-0,Some common heterocyclic compound, 10259-22-0, name is Ethyl 3-methoxybenzoate, molecular formula is C10H12O3, 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.

General procedure: To a stirred solution of 1a (0.15 g, 1.0 mmol) in THF (8 mL) at -78 C was added n-BuLi (1.6 M in hexane; 2.0 mmol) dropwise.The temperature was gradually raised to 0 C and stirring was continued for 1.5 h. The mixture was cooled again to -78 C and ethyl benzoate (0.15 g, 1.0 mmol) was added dropwise. After the temperature was gradually raised to 0 C, saturated aqueous NH4Cl (20 mL) was added and the mixture was extracted with AcOEt (3 × 15 mL). The combined extracts were washed with brine (20 mL), dried (Na2SO4), and concentrated by evaporation. The residue was purified by column chromatography on SiO2(AcOEt/hexane 1:5) to afford 3a (0.16 g, 63%); a yellow solid

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

Reference:
Article; Kobayashi, Kazuhiro; Fujiwara, Daiki; Nozaki, Kazuma; Nogi, Takashi; Heterocycles; vol. 96; 9; (2018); p. 1610 – 1621;,
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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. 625-56-9, name is Chloromethyl acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Chloromethyl acetate

To a suspension of 3- (3, 5-dimethyl-IH-pyrrol-2-ylmethylene)-1, 3-dihydro-indol-2-one (2. 02 g, 8.5 mmoles) and Cs2C03 (11.05 g, 34 mmoles) in CH3CN (200 mL) was added acetic acid chloromethyl ester (3.3 mL, 34 mmoles). The reaction mixture was heated at 40C and left under stirring overnight. The reaction evolution was followed by LC/MS. The mixture was then concentrated in vacuo together with silica gel. The residue was purified by chromatography using a gradient of petroleum ether/ethyl acetate from 85: 15 to 50: 50, furnishing the title compound (488 mg, 19% yield) as a deep orange solid. 1H-NMR (DMSO-d6, Z isomer) 8 13.01 (s, lH), 7.81 (d, lH), 7.65 (s, lH), 7.26-7. 05 (m, 3H), 6.07 (d, lH), 5.89 (s, 2H), 2.35 (s, 3H), 2.33 (s, 3H), 2.04 (s, 3H).

The synthetic route of 625-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEO PHARMA A/S; WO2005/58309; (2005); A1;,
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Related Products of 27492-84-8,Some common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, molecular formula is C9H11NO3, 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.

Methyl 2-methoxy-4-aminobenzoate (10g, 55.25mmol) and hydroxylamine hydrochloride (15.36g, 221mmol) were taken up in MeOH (80ml) and a solution of KOH (15.4g, 275mmol) in MeOH (55ml) was added carefully. The resultant mixture was stirred at reflux for 36hrs. The volatiles were removed in vacuo. The residue was taken up in 1 M NaOH (50ml) and washed with ethyl acetate (EtOAc, 50ml). Concentrated HCl was added slowly until precipitation of a solid (pH was 10). The solid was filtered off, washed with H2O, then methyl-tert-butyl ether (MTBE) and dried under vacuum. 1H NMR showed the solid contained approx. 1/3 molar equivalent of ethyl acetate. The solid was taken up in 1M NaOH (100ml) and the EtOAc was removed in vacuo. Concentrated HCl was added carefully until precipitation of a solid (pH was 8). The solid was collected by filtration, washed with H2O, then MTBE and dried under vacuum to give 4.67g (47%) of the title compound as a dark red solid.1H NMR (delta, 250MHz, d6-DMSO): 3.75 (s, 3-H, OMe), 5.64 (s, 2-H, NH2), 6.14 (dd, 1-H, aromatic), 6.18 (brs, 1-H, aromatic), 7.48 (d, 1-H, aromatic), 8.73 (s, 1-H, NH), 10.06 (s, 1-H, OH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-2-methoxybenzoate, its application will become more common.

Reference:
Patent; Nogra Pharma Limited; NACCARI, Giancarlo; BARONI, Sergio; EP1910275; (2013); B1;,
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