Tag: M.W=100-200

Reference of 816-27-3, 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 816-27-3 as follows.

To a suspension of 3-methoxy-benzene-1,2-diamine sulfate, Example 25(b), (2.36 g, 10 mmol) in EtOH (15 mL) and H2O (1 mL) was added NaHCO3 (1.68 g, 20 mmol, J T Baker). When gas evolution was complete, ethoxy-imino-acetic acid ethyl ester (1.6 g, 11 mmol, prepared according to J. Chem. Soc. Perkin. Trans. 1, 1999, 1789) was added and the mixture was stirred at room temperature for 16 h. The reaction was diluted with sat. aq. NaHCO3 and extracted with 25% i-PrOH(CHCl3 (5¡Á). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (gradient: 0-5% MeOH/CH2Cl2) afforded 3-amino-8-methoxy-1H-quinoxalin-2-one as a light-brown powder [MS (ESI, pos. ion) m/z: 192 (M+1)] and 3-amino-5-methoxy-1H-quinoxalin-2-one as a light-brown powder [MS (ESI, pos. ion) m/z: 192 (M+1)].

According to the analysis of related databases, 816-27-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wang, Hui-Ling; Balan, Chenera; Doherty, Elizabeth M.; Falsey, James R.; Gore, Vijay Keshav; Katon, Jodie; Norman, Mark H.; US2005/176726; (2005); 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 34837-84-8 as follows. Recommanded Product: Methyl 2-(4-fluorophenyl)acetate

Step El. To a solution of diisopropylamine (4.24 mL, 29.7 mmol) in THF (100 mL) at -5 ¡ãC under nitrogen was added a solution of 2.5 M n-butyllithium in hexanes (11.9 mL, 29.7 mmol) dropwise via syringe. After stirring for 15 min, methyl 2-(4-fluorophenyl)acetate (commercially available, 5.0 g, 29.7 mmol) was added. The mixture was stirred at -5 ¡ãC for 30 min and then treated with iodomethane (1.86 mL, 29.7 mmol). The reaction mixture was allowed to gradually warm to rt. After 4 h at rt, the reaction mixture was poured into a solution of aqueous ammonium chloride. The resulting mixture was extracted with diethyl ether. The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. The crude product was purified using silica gel column chromatograpy (20: 1 hexane/ethyl acetate) to afford methyl 2-(4- fluorophenyl)propanoate (2.32 g, 43 percent yield) as a clear liquid. 1H NMR (500 MHz, chloroform-d) delta 7.33 – 7.25 (m, 2H), 7.09 – 6.98 (m, 2H), 3.73 (q, J=7.2 Hz, IH), 3.69 (s, 3H), 1.51 (d, J=7.2 Hz, 3H).

According to the analysis of related databases, 34837-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence R.; HIGGINS, Mendi A.; BRONSON, Joanne J.; ZUSI, F. Christopher; MACOR, John E.; DING, Min; WO2015/42243; (2015); 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. 140-39-6, name is p-Tolyl Acetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of p-Tolyl Acetate

A mixture of 40.0 g (0.27 mol) of p-tolyl acetate and 45.0 (0.34 mol) of AlCl3 was slowly (for ca. 0.5 hr) heated to 120-125 C. This mixture was stirred at this temperature for 1 hr, and then 500 mL of 2M HCl was added at 0 C. The product was extracted with 3*100 mL of diethyl ether, the combined extract was dried over Na2SO4 and then evaporated to dryness. This procedure gave 39.7 g (99%) of the title product which was further used without an additional purification.

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 140-39-6.

Reference:
Patent; Giesbrecht, Garth R.; Boller, Timothy M.; Voskoboynikov, Alexander Z.; Asachenko, Andrey F.; Nikulin, Mikhail V.; Tsarev, Alexey A.; US2011/98425; (2011); A1;,
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5445-17-0, name is Methyl 2-bromopropanoate, belongs to esters-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. Quality Control of Methyl 2-bromopropanoate

EXAMPLE 11A 2-[4-(5-Trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-propionic acid methyl ester A solution of 1-(5-trifluoromethyl-pyridin-2-yl)-piperazine (0.9 g, 3.9 mmoles) in MeOH (13 mL) and DIPEA (1.5 mL) was treated with 2-bromo-propionic acid methyl ester (0.48 mL, 4.3 mmoles) and stirred overnight at 70 C. MeOH was removed under reduced pressure and the residue was purified (silica gel, 10-40% acetone in hexane) to provide the title compound as a yellowish solid (1.23 g, 99%).

The synthetic route of 5445-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoff, Ethan D.; Link, James T.; Pliushchev, Marina A.; Rohde, Jeffrey J.; Winn, Martin; US2005/261302; (2005); A1;,
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3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, belongs to esters-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: C9H16O3

Step A: ethyl 4-iodocyclohexanecarboxylateTo a solution of ethyl 4-hydroxycyclohexane carboxylate (10.0 g, 58.1 mmol) inCH2C12 (200 mL) at 0 C was added imidazole (1 1.86 g, 174.0 mmol), triphenylphosphine (25.9 g, 99.0 mmol), and followed by iodine (25.05 g, 99.0 mmol) several portions over a period of 45 min. The resulting suspension was gradually allowed to warm up to rt. After stirring at rt over night, the mixture was partitioned between Et20 (200 mL) and water (200 mL). The organic layer was washed with saturated Na2S203 ( 100 mL) and brine (3×1 OOmL), dried over MgS04, and concentrated. The residue was purified by flash chromatography (Biotage 40+M) using 10- 20% EtOAc hexane gradient, affording the title compound: .H NMR (500 MHz, CDC13) delta 5.70 (m, IH), 4.20-4.10 (m, 2H), 2.58 (m, IH), 2.48-1.60 (m, 8H), 1.28 (mf 3H).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; NARGUND, Ravi; LO, Michael Man-Chu; YAN, Lin; HUO, Pei; FRANKLIN, Christopher; WO2011/53519; (2011); A1;,
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Application of 23426-63-3, These common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, 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 stirred solution of 4-bromo-lH-pyrazole (3.0 g, 20.41 mmol) in dry DMF (30 ml) was added Cs2C03 (19.95 g, 61.23 mmol) and methyl 2-bromo-2-methylpropanoate (3.96 ml, 30.61 mmol) at room temperature under an atmosphere of nitrogen. Then the reaction mixture was stirred at 80 C for 18 hours. After completion of reaction (monitored by TLC), the reaction mixture was diluted with ice cold water (30 ml) and extracted with ethyl acetate (2 x 50 ml). The combined organic layers were washed with brine (50 ml), dried over anhydrous Na2S04 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford the title compound (3.0 g, 60 %). 1H NMR (400 MHz, DMSO-de): 1.76 (s, 6H), 4.63 (s, 3H), 7.61 (s, 1H), 8.21 (s, 1H).

Statistics shows that Methyl 2-bromo-2-methylpropanoate is playing an increasingly important role. we look forward to future research findings about 23426-63-3.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; WILSON, Jonathan, E.; BRUCELLE, Francois; LEVELL, Julian, R.; (153 pag.)WO2019/161162; (2019); A1;,
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Reference of 107582-20-7, A common heterocyclic compound, 107582-20-7, name is Methyl 2,3-diaminobenzoate, molecular formula is C8H10N2O2, 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.

General procedure: 800 mg (4.4 mmol) s3 was dissolved in 10 mLacetic acid, 336 mg (4.8 mmol) sodium nitrite was added slowly.The mixture was stirred for 18 h at room temperature, then poured into 30 mL water, neutralized with saturated solution of sodium bicarbonate, extracted with 50 mL ethyl acetate, washed with 20 mL water, dried with anhydrous sodium sulfate overnight. The filtrate was concentrated by vacuum distillation to obtain brown solid, recrystallized from ethyl acetate and hexane to afford pale brown solid of s4 300 mg, yield 35percent.1H NMR(400 MHz, CDCl3): d8.78 (s, 1H, ArH), 8.19 (d, 1H, J = 8.8 Hz, ArH), 7.55 (d, 1H, J = 8.8 Hz, ArH), 4.33 (s, 3H, OCH3), 3.98 (s, 3H, NCH 3 );13C NMR (100 MHz,CDCl3): d 166.6, 145.6, 135.6, 128.2, 126.3, 122.9, 109.0, 52.4, 34.4.HRMS (EI) calcd. for C9H9N3O2 [M]+: 191.0695, found 191.0697.

The synthetic route of 107582-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Kang; Chen, Jian-Qin; Shi, Yan-Xia; Sun, Mei-Jian; Li, Peng-Fei; Zhao, Zhen-Jiang; Zhu, Wei-Ping; Li, Hong-Lin; Xu, Yu-Fang; Li, Bao-Ju; Qian, Xu-Hong; Chinese Chemical Letters; vol. 28; 4; (2017); p. 919 – 926;,
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Synthetic Route of 56741-34-5, A common heterocyclic compound, 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, molecular formula is C8H8FNO2, 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.

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey solid

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:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, 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 13831-03-3, Product Details of 13831-03-3

General procedure: To a stirred solution of the acetylenic ester (2 mmol) and the 1,3-diketones (2 mmol) in 10 mL of CH2Cl2 was added 0.26 g of isoquinoline (2 mmol) at r.t. After completion of the reaction (2-3 h), as indicated by TLC (AcOEt/hexane, 1:2), the solvent was removed under reduced pressure and the viscous residue was purified by column chromatography on silica gel (Merck 230-400 mesh) using hexane-AcOEt (2:1) as eluent to afford pure title compounds.

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, tert-Butyl propiolate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Piltan, Mohammad; Yavari, Issa; Moradi, Loghman; Journal of the Iranian Chemical Society; vol. 13; 4; (2016); p. 605 – 608;,
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Reference of 2216-92-4, A common heterocyclic compound, 2216-92-4, name is N-Phenylglycine Ethyl Ester, molecular formula is C10H13NO2, 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.

Prepared in the manner of Example 16 except 4- (trifluoromethyl) benzyl bromide was substituted for 4-chlorobenyl chloride. Purification by flash chromatography (10: 1 to 5: 1 hexanes/EtOAc) afforded the title compound as a yellow oil (30%). 1H NMR [(CDCI3)] [8] 7.62 (d, 2H), 7.52 (d, 2H), 7.43 (d, 2H), 6.68 (d, 2H), 4.73 (s, 2H), 4.25 (q, 2H), 4.14 (s, 2H), 1.30 (t, 3H). Anal. Calc. [FOR C21H18NO3FS] : C, 50.11 ; H, 3.60 ; N, 2.78. Found: C, 50.01 ; H, 3.98 ; N, 2.61. HRMS (MH+). Calc. : 504.1221. Found: 504.1227.

The synthetic route of 2216-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2003/99769; (2003); A1;,
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