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. 13195-64-7, name is Diisopropyl malonate, A new synthetic method of this compound is introduced below., Formula: C9H16O4

Example 1Preparation of Protected Diester 2 The dihydroisoquinoline 1 (1.0 eq.) and Boc anhydride (1.5 eq.) were dissolved in CH2Cl2 at room temperature to provide a 1.5 M solution with respect to the dihydroisoquinoline. The mixture was allowed to stir for 30 min. Following the allotted time, the reaction mixture was cooled to 0° C. and then diisopropylmalonate (1.5 eq.) followed by a pre-chilled solution of the Pd catalyst (0.008 eq.) in dichloromethane were added successively to the reaction mixture to provide a final reaction concentration of 0.84 M with respect to the starting dihydroisoquinoline. The reaction mixture was allowed to continue stirring at 2.5° C. for 15 h. Following this time EtOAc and brine were added to the reaction mixture. The aqueous layer was extracted with three portions of EtOAc and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the crude product. The crude material was dissolved in a minimal amount of dichloromethane and purified by flash chromatography on SiO2 (15-30percent EtOAc-hexanes, elution was observed at 285 nm and 228 nm). The product 2 was a colorless solid that existed as a mixture of rotamers in solution at room temperature 94percent: [alpha]26D -69.0 (c 0.21, CHCl3); 1H NMR (CDCl3) delta 0.81-1.02 (m, 6H), 1.06-1.17 (m, 6H), 1.23-1.38 (m, 9H), 2.51-2.63 (m, 1H), 2.64-2.77 (m, 1H), 3.20-3.29 (m, 0.6H), 3.32-3.41 (m, 0.4H), 3.51-3.58 (m, 1H), 3.62-3.70 (m, 6H), 3.70-3.76 (m, 0.4H), 3.91-4.01 (m, 0.6H), 4.65-4.82 (m, 1H), 4.83-4.98 (m, 1H), 5.71 (apparent d, J=5.7 Hz, 0.6H), 5.78 (apparent d, J=7.9 Hz, 0.4H), 6.42-6.49 (m, 1H), 6.77 (s, 0.6H), 6.81 (s, 0.4H); 13C NMR (CDCl3) delta 21.02, 21.09, 21.18, 21.32, 27.24, 27.95, 28.02, 37.60, 39.34, 52.11, 52.83, 55.48, 55.52, 59.28, 60.08, 68.58, 68.76, 68.82, 79.46, 80.03, 110.09, 110.73, 111.13, 126.11, 126.18, 126.37, 127.07, 146.81, 146.87, 147.93, 153.86, 154.30, 166.29, 166.78, 166.94, 167.06.

The synthetic route of 13195-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENERAL ELECTRIC COMPANY; US2008/306269; (2008); A1;,
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Reference of 36692-49-6,Some common heterocyclic compound, 36692-49-6, name is Methyl 3,4-diaminobenzoate, molecular formula is C8H10N2O2, 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 suspension of methyl 3,4-diaminobenzoate (10.0 g, 60.2 mmol) and N-hydroxyethanimidamide (10.6 g, 95 % purity, 135 mmol) in dioxane (20 mL) was addedcaesium carbonate (19.6 g, 60.2 mmol) and the mixture was stirred at 110 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (sodium sulfate), filtered and the solvent was removed in vacuum to give a solid that was triturated with methanol to give 8.00 g (70 % yield) of the title compound.LC-MS (Method 2): R1 = 0.67 mm; MS (ESIpos): m/z = 191 [M+H]1H-NMR (400 MHz, DMSO-d6)oe [ppm]: 2.308 (16.00), 4.831 (2.74), 5.429 (3.11), 6.583 (2.69),6.603 (2.81), 7.148 (1.50), 7.153 (1.72), 7.169 (1.30), 7.174 (1.62), 7.212 (3.04), 7.217 (2.53).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
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Application of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

[286] Step 3: methyl 2-[5-bromo-2-(4-methylbenzoylimino)benzo[d]thiazol-3(2H)-yl]butanoate[287] To a stirred solution of N-(5-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide (90 mg, 0.258 mmol) prepared in Step 2 in N,N-dimethylformamide (3.0 mL) were added methyl 2-bromobutyrate (93.9 mg, 0.519 mmol) and potassium carbonate (107 mg, 0.768 mmol). The reaction mixture was stirred at 80 ? for 3 hours. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 10/1) to give 109.5 mg of the titled compound as a white solid (Yield: 94%)[288] 1H NMR (CDCl3, 400 MHz) delta 8.18(d, 2H), 7.56(d, 1H), 7.42(s, 2H), 7.28(d, 2H), 5.46(brs, 1H), 3.67(s, 3H), 2.47-2.54(m, 2H), 2.42(s, 3H), 0.92(t, 3H)

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
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Some common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, molecular formula is C6H8O2, 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: C6H8O2

00727] (i) Production of ethyl 2-methylpyrazolo[l,5-a]pyridine-3-carboxylate [00728] To a suspension of 1-aminopyridinium iodide (125 g, 0.56 mmol) in N,N-dimethylformamide (1.2 L) were added ethyl 2-butynoate (54.0 g, 0.48 mmol) and potassium carbonate (79 g, 0.56 mmol) and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water (500 mL), ethyl acetate (500 mL) and hexane (500 mL), and the precipitated solid was collected by filtration, and washed with water (500 mL). The filtrate was extracted with a mixed solvent (1.5 L x 2) of ethyl acetate/hexane (1: 1) and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The residue obtained by concentration of the filtrate and the solid collected by filtration in the above were combined, washed with diethyl ether (25 mL) and hexane (25 mL) and dried to give the title compound (36.0 g, 37%) as a white solid. The washing solution was concentrated, and the obtained residue was washed with diethyl ether (10 mL) and hexane (10 mL) and dried to give a second crop (11.0 g, 11%) of the title compound as a white solid. The washing solution of the second crop was concentrated, and the obtained residue was purified using a pad (elution solvent: ethyl acetate/hexane=l/l) with silica gel and activated carbon in 2 layers, washed with diethyl ether (5.0 mL) and hexane (5.0 mL) and dried to give a third crop (6.5 g, 7%) of the title compound as a white solid (total yield 55%).[00729] 1H-NMR (DMSOd6, 300 MHz) delta 1.35 (3H, t, J = 7.2 Hz), 2.57 (3H, s), 4.30 (2H, q, J = 7.2 Hz), 7.09 (IH, dt, J = 1.5, 6.9 Hz), 7.49 – 7.61 (IH, m), 8.00 (IH, td, J = 1.3 Hz), 8.75 (IH, td, J = 1.0, 6.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4341-76-8, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan; WO2010/90716; (2010); 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. 33842-16-9, name is Methyl benzo[d][1,3]dioxole-4-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl benzo[d][1,3]dioxole-4-carboxylate

A mixture of the material so obtained, a 2N aqueous potassium hydroxide solution (15.5 ml) and methanol (40 ml) was stirred at ambient temperature for 2 hours. The solution was concentrated to about one quarter of the original volume and cooled in an ice bath. The mixture was acidified to pH 3.5 by the addition of a 2N aqueous hydrochloric acid solution. The resultant precipitate was collected by filtration and washed in turn with water and diethyl ether. There was thus obtained 2,3-methylenedioxybenzoic acid (1.87 g); NMR Spectrum: (DMSOd6) 6.1 (s, 1H), 6.9 (t, 1H), 7.15 (d, 1H), 7.3 (d, 1H), 13.0 (br s, 1H).

The synthetic route of 33842-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/4732; (2004); A1;,
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Reference of 110104-60-4, These common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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 2 Production of 4-methoxy-2(5H) thiophenone from 4-chloro-3-methoxy-2E-butenoic acid methyl ester and sodium hydrogen sulfide 11.6 g (0.14 mol) of 90 percent sodium hydrogen sulfide monohydrate is dissolved in 90 ml of methanol. A solution of 17.0 g (0.1 mol) of 96.7 percent 4-chloro-3-methoxy-2E-butenoic acid methyl ester in 10 ml of methanol is instilled into this solution at 50 C. in 4 hours. It is stirred for another 2 hours and the methanol is then distilled off under vacuum on the rotary evaporator. The residue is mixed with 100 ml of water and extracted twice with 80 ml each of methylene chloride. The organic phase is dried over sodium sulfate and concentrated by evaporation. The residue is recrystallized hot from 15 ml of ethanol. 5.12 g of yellow-colored product with a melting point of 90 C. is obtained. Further data concerning the compound is: content (GC): 96 percent; yield: 37.8 percent.

Statistics shows that (E)-Methyl 4-chloro-3-methoxybut-2-enoate is playing an increasingly important role. we look forward to future research findings about 110104-60-4.

Reference:
Patent; Lonza Ltd.; US4906759; (1990); A;,
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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 383-62-0 as follows. Quality Control of Ethyl 2-chloro-2,2-difluoroacetate

[0068] Synthesis of Compound B: A mixture of Compound A (3g, 1 eq), K2CO3 (3.06g, 2 eq), ethyl chlorodifluoroacetate(2.2g, 1.3 eq) in DMF (20 ml), was heated at 75C overnight. The reaction was monitored by TLC. After completion, themixture was poured into cold water (50 ml) and extracted with ethyl acetate (3350 ml). The combined organic layer waswashed with water (2330 ml), saline solution (20 ml) and dried over anhydrous sodium sulfate. Purification of the crudeproduct by column chromatography (10% ethyl acetate in hexane) yielded 1 g of the desired product. 1H NMR (DMSOd6)Theoretical MS for C17H11F3NO3: 320.26; M++ 1 found, 321.1

According to the analysis of related databases, 383-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Artax Biopharma Inc.; GAGETE MATEOS, Andres; CASTRO PALOMINO, Julio; MARTI CLAUZEL, Luc; TORMO CARULLA, Damia; (23 pag.)EP3059232; (2016); A1;,
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Synthetic Route of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

Compound I-CC (3.1 g, 17.1 mmol) and aniline (1.59 g, 17.1 mmol) were dissolved in 30 mL of acetonitrile in a glass pressure tube. After the addition of potassium carbonate (4.71 g, 34.2 mmol) and potassium iodide (0.283 g, 1.71 mmol), the tube was sealed and mixture was stirred for 18 hr at 100 C. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried over a2S04, filtered, evaporated down and purified by silica column (hexane:EtOAc) to give Compound II-CC (1.97 g, 59%); LCMS:194.12 m/z (M+H)+.

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

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; GALEMMO, Robert, A., Jr.; ARTIS, Dean, Richard; YE, Xiaocong, Michael; AUBELE, Danielle, L.; TRUONG, Anh, P.; BOWERS, Simeon; HOM, Roy, K.; ZHU, Yong-Liang; NEITZ, R., Jeffrey; SEALY, Jennifer; ADLER, Marc; BEROZA, Paul; ANDERSON, John, P.; WO2011/79114; (2011); A1;,
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Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, 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.

Step A: A solution of methyl 4-methoxybutanoate (1.48 g, 1.0 equiv) in methanol was treated with LiOH.H2O (3.1 equiv), and the mixture was heated to 50 C. for 3 hours. The mixture was cooled to ambient temperature and 5.0 N HCl (7.0 mL) was added. The mixture was concentrated to dryness under reduced pressure, CH2Cl2 was added and the mixture sonicated for 30 minutes. The insoluble salts were removed by vacuum filtration and the filtrate concentrated to afford 4-methoxybutanoic acid as a colorless oil (1.023 g, 77%).

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-methoxybutanoate, its application will become more common.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 105-53-3, name is Diethyl malonate, belongs to esters-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 105-53-3, Recommanded Product: 105-53-3

Step 1: Into a 5 L 4 necked round bottomed flask was placed a solution of diethyl malonate (300 g, 1.87 mol) and 1,2-dibromoethane (634.5 g, 3.38 mol) in DMSO (1.5 L). The mixture was treated with K2C03 (1020 g, 7.39 mol) and Bu4NHSO4 (6.4 g, 19 mmol). The resulting solution was allowed to stir for 48 h at room temperature. The reaction mixture was treated with 2 L of H20 and extracted with 1.5 L of EtOAc (3x). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. The residue was distilled under 5-10 mmHgvacuum at 64-65 C. This resulted in 400 g (90%) of diethyl cyclopropane-1,1-dicarboxylate as an oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diethyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (107 pag.)WO2016/144848; (2016); A1;,
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