Tag: M.W=100-200

7462-74-0, 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. 7462-74-0, name is 2-Bromo-2-methylpropanamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 5 (R)-2-(3-N,N-Dibenzylamino-3,4-dihydro-2H-1-benzopyran-5-yloxy)-2-methylpropanamide (R)-3-N,N-Dibenzylamino-5-hydroxy-3,4-dihydro-2H-1-benzopyran (35.4 g, 100 mmol) was dissolved in anhydrous 1,4-dioxane (350 mL) under nitrogen. A dispersion of sodium hydride (60-65% in oil, 5.33 g, 130 mmol) was added in portions. The mixture was stirred for 2 h at room temperature. 2-Bromo-2-methylpropanamide (17.9 g, 110 mmol; described in Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc. Perkin Trans. 1 1990, 767-771) was added to the dark greenish solution and was heated at reflux with stirring for 3 h. After cooling, a small amount of water was added, the solution was decanted, and the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (350 mL) and a saturated NaHCO3 solution (50 mL). The organic layer was dried (MgSO4), and the solvent was removed in vacuo to give a brownish residue which was chromatographed on a short column of silica gel (eluent: hexane/ethyl acetate; 55:45) affording 27.6 g (64% yield) of the title compound as a white solid: mp 132-134 C.; [alpha]22D-92 (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 430 (6, M+).

The synthetic route of 7462-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astrazeneca AB; US6479497; (2002); B1;,
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These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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. 16066-84-5

To a stirred suspension of 6-iodo-3 -((8-methoxy-2-(6-methoxypyridin-3 -yl)-2,3dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-3H-imidazo[4, 5-b]pyridine (0.20 g, 0.38 mmol, Example 1-52-9) in 1,4-dioxane (5 mL) was added tert-butyl-N-methylcarbamate (0.10 g,0.75 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.018 g, 0.019 mmol), 4,5- bi s(diphenylphosphino)-9, 9-dimethylxanthene (0.044 g, 0.075 mmol) and cesium carbonate (0.18 g, 0.57 mmol). The mixture was degassed under vacuum/backfilled with nitrogen (x3). The mixture was then heated to 115 C. After 18 h, the mixture was allowed to cool to room temperature and was concentrated. Chromatographic purification of the crude product(Biotage, 12 g silica gel column, ethyl acetate/heptane elute) provided semi-pure material. This material was dissolved in dichloromethane (10 mL) and was treated with trifluoroacetic acid (6 mL). The mixture was allowed to stir at room temperature. After 15 mm, the mixture was concentrated. The residue was dissolved in methanol and was neutralized by the addition of solid potassium carbonate. The mixture was filtered and concentrated.Chromatographic purification of the crude product (Biotage, 12 g silica gel column, 0-8% methanol/ethyl acetate elute) provided 0.020 g (12%) of 3-((8-methoxy-2-(6- methoxypyridin-3 -yl)-2,3 -dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-N-methyl-3H- imidazo[4,5-b]pyridin-6-amine as a light yellow solid: ?H NIVIR (400 IVIFIz, CDC13) 8.22 – 8.18 (m, 1H), 7.95 (d, J= 2.5 Hz, 1H), 7.92 (s, 1H), 7.61 (dd, J= 8.6, 2.5 Hz, 1H), 7.28 (d, J= 2.5 Hz, 1H), 6.77 (dd, J= 8.5, 0.7 Hz, 1H), 6.54 – 6.48 (m, 2H), 5.30 (s, 2H), 5.09 (dd, J8.4, 2.5 Hz, 1H), 4.29 (dd, J= 11.6, 2.5 Hz, 1H), 4.06 (dd, J= 11.6, 8.4 Hz, 1H), 3.93 (s, 3H), 3.79 (s, 3H), 2.91 (s, 3H) ppm; (M+1) = 434.

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 16066-84-5.

Reference:
Patent; GENZYME CORPORATION; KANE, John, L., Jr.; BARBERIS, Claude; CZEKAJ, Mark; ERDMAN, Paul; GIESE, Barret; KOTHE, Michael; LE, Tieu-binh; LIU, Jinyu; MA, Liang; METZ, Markus; PATEL, Vinod; SCHOLTE, Andrew; SHUM, Patrick; WEI, Limli; (408 pag.)WO2017/15267; (2017); A1;,
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A common compound: 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 16982-21-1

N,6-dimethylnicotinohydrazide (23a, 0.1 g, 0.61 mmol) and ethyl 2-amino-2-thioxoacetate (0.089 g, 0.67 mmol) in toluene (0.5 mL) and acetic acid (0.05 mL) were stirred at 90 C for 10 hours. The reaction mixture was purified by preparative HPLC using a Gemini NX reverse-phase column (C-18, 5 microns silica, 30 mm diameter, 150 mm length, flow rate of 60 ml / minute) using an isocratic mixture of 17% acetonitrile in water (containing ammonium carbonate (2 g / L). The fractions containing the desired compound were evaporated to dryness to afford ethyl 1-methyl-5-(6-methylpyridin-3-yl)-1H-1,2,4-triazole-3-carboxylate (34a, 0.083 g, 55%) as a yellow crystalline solid: 1H NMR (500 MHz, DMSO-d6) delta 8.87 (d, J = 1.9 Hz, 1H), 8.13 (dd, J = 1.9, 8.1 Hz, 1H), 7.49 (d, J = 8.1 Hz, 1H), 4.36 (q, J = 7.1 Hz, 2H), 4.06 (s, 3H), 2.58 (s, 3H), 1.33 (t, J = 7.1 Hz, 3H); 13C NMR (126 MHz, DMSO-d6) delta (ppm) 161.34, 158.91, 156.03, 151.34, 150.14, 136.39, 124.11, 118.93, 63.45, 37.12, 24.34, 14.38; HRMS, ESI+ m/z, (M+H)+ calculated for C12H14N4O2 257.10330; found, 247.11879 (tR = 1.20 min., purity = 100%).

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, 16982-21-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Degorce, Sebastien; Delouvrie, Benedicte; Davey, Paul R.J.; Didelot, Myriam; Germain, Herve; Harris, Craig S.; Brempt, Christine Lambert-Van Der; Lebraud, Honorine; Ouvry, Gilles; Tetrahedron Letters; vol. 53; 45; (2012); p. 6078 – 6082;,
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78888-18-3, 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. 78888-18-3, name is tert-Butyl allylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of N-tert-butoxycarbonyl prop-2-enylamine 2A(20 g, 127.39 mmoL) was dissolved in Nu, Nu-dimethylformamide (100 mL), sodium sulphate(7.6 g, 60 / , 191.08 mmoL) was treated with n-hexane and then added with N, N-dimethylformamide (400 mL) and added dropwise to the reaction solution at 0 C under nitrogen C for 30 minutes, and the reaction was continued at room temperature for 20 minutes.A mixture of proparagyl bromide (30.3 g, 245.78 mmoL) was added dropwise to the ice bath and the mixture was stirred at 0 C for 30 minutes. The reaction solution was slowly added to crushed ice to deal with excess sodium hydride, extracted with ethyl acetate (100 mL chi3), the organic phases were combined and washed with saturated brine (100 mL x 3), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure The The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (nu / nu) = 100: 1 to 50: 1) to give yellow liquid 2B (21 g, yield 85%).

The synthetic route of 78888-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; FAN, JIANG; FENG, JIAN-CHUAN; PENG, FEI; CHEN, QING-PING; (89 pag.)TW2017/8224; (2017); A;,
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57561-39-4, These common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, 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.

2-(Boc-methyl-amino)-ethanol (0.19 g, 1 mmol) was dissolved in 4 mL of dichloromethane, and added with Dess-Martin periodinane (0.64 g, 1.5 mmol), and stirred at room temperature for 1 hour. 3 mL of a saturated sodium thiosulfate solution and 5 mL of a saturated sodium bicarbonate solution were added to the reaction mixture, and the mixture was stirred until clarified. Then, it was extracted with 20 mL of dichloromethane, and the dichloromethane layer was concentrated under reduced pressure. The residues were dissolved in 5 mL of acetic acid, and added with ethyl 5-bromo-3-amino-2-methyl-benzoate 1c (0.26 g, 1 mmol). The sodium borohydride (0.22 g, 6 mmol) was added portionwise and then stirred at room temperature for 0.5 hour. The reaction solution was added with water and ethyl acetate. The ethyl acetate layer was washed with aqueous solution of sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residues were purified by column chromatography (eluent: petroleum ether:ethyl acetate 30:1 to 3:1) to give 0.3 g of title product.

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 57561-39-4.

Reference:
Patent; ANCUREALL PHARMACEUTICAL (SHANGHAI) CO., LTD.; Si, Jutong; Wang, Guan; Jiang, Meifeng; YANG, Zhihe; Zhou, Chentao; (118 pag.)US2019/345139; (2019); A1;,
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354-38-1, 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. 354-38-1, name is 2,2,2-Trifluoroacetamide, This compound has unique chemical properties. The synthetic route is as follows.

Prepared from Intermediate 5 by a method analogous to that reported by Bolm et ah, Organic Letters, 2004, 6(8), 1305-1307, using trifluoroacetamide and (diacetoxy- iodo)benzene in the presence of dirhodium tetraacetate. 5H (500 MHz, CDCI3) 8.79 (d, J 1.4 Hz, IH), 8.22-8.19 (m, IH), 8.18 (dd, J8.4, 2.0 Hz, IH), 3.56 (s, 3H).

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; UCB BIOPHARMA SPRL; CHOVATIA, Prafulkumar Tulshibhai; HUTCHINGS, Martin Clive; KROEPLIEN, Boris; REUBERSON, James Thomas; (102 pag.)WO2016/198401; (2016); A1;,
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The chemical industry reduces the impact on the environment during synthesis 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, I believe this compound will play a more active role in future production and life. 112257-19-9

To a solution of 2 (465mg, 2.66mmol) in CH2Cl2 (20mL) was added 8 (500mg, 2.66mmol) and sodium triacetoxyborohydride (1.13g, 5.32mmol) at 0¡ãC under argon and then stirred at room temperature for 12h. The reaction solution was quenched with saturated NH4Cl (20mL) and extracted with CH2Cl2 (30mL ¡Á 3), and the combined organic layers dried with Na2SO4. The residue was purified by column chromatography on silica gel using EtOAc/petroleum ether (1/2, V/V) as elunt to give 10 as colorless oil (750mg, 81percent); 1H NMR (400MHz, DMSO) delta 6.49 (d, J = 3.2Hz, 1H, Ar-H), 6.35 (d, J = 3.2Hz, 1H, Ar-H), 3.52 (s, 2H, CH2), 3.29-3.20 (m, 2H, CH2), 2.76 (d, J = 9.8Hz, 3H, CH3), 2.42 (t, J = 6.7Hz, 2H, CH2), 2.18 (s, 3H, CH3), 1.45 (s, 9H, (CH3)3); HRMS (ESI) m/z [M+H]+ Calcd for C14H24BrN2O3+: 347.0970. Found: 347.0974.

The chemical industry reduces the impact on the environment during synthesis 112257-19-9. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yang, Hao; Ouyang, Yifan; Ma, Hao; Cong, Hui; Zhuang, Chunlin; Lok, Wun-Taai; Wang, Zhe; Zhu, Xuanli; Sun, Yutong; Hong, Wei; Wang, Hao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 20; (2017); p. 4635 – 4642;,
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Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, molecular formula is C3H6ClNO, 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. 96-30-0

X-2 100 mg (0.288 mmol), 2-chloro-N-methylacetamide 37 mg (0.344 mmol), Cs2CO3281 mg (0.862 mmol) and 10 mL DMF were added to a 100 mL single-necked flask.The reaction was carried out at 50 degrees overnight, and the reaction was complete by TLC. The reaction solution was poured into 50 mL of water.EA was extracted with 30 mL*3, and the organic phase was combined with a sand column to obtain 80 mg of a white solid.Yield 66.4%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 96-30-0, its application will become more common.

Reference:
Patent; China Pharmaceutical University; Lu Tao; Zhang Li; Zhao Jingyun; Zhang Beichen; Chen Yadong; (19 pag.)CN109897054; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 226260-01-1, name is 3-Fluoro-N-methoxy-N-methylbenzamide, A new synthetic method of this compound is introduced below., 226260-01-1

2. 35 ml of a 1 molar solution of vinylmagnesium bromide in THF is added dropwise under nitrogen to a solution, held at 0 C., of 5.80 g (31.6 mmol) of 3-fluoro-N-methoxy-N-methylbenzamide in 70 ml of THF.The reaction mixture is stirred at room temperature for 40 minutes, then saturated ammonium chloride solution is added, and the mixture is stirred at room temperature for a further 10 minutes. tert-Butyl methyl ether is added to the reaction mixture. The organic phase is separated off, washed with sodium hydrogencarbonate solution and water and dried in vacuo: 1-(3-fluorophenyl)-3-(methoxymethylamino)propan-1-one as yellow oil; ESI 212.

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; Dorsch, Dieter; Schadt, Oliver; Blaukat, Andree; US2008/249095; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

24243-71-8, Adding some certain compound to certain chemical reactions, such as: 24243-71-8, name is Propane-1-sulfonamide, 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 24243-71-8.

A mixture of 2′-chloro-6′-(2,6-dimethylphenoxy)-1,5-dimethyl43,4′-bipyridin]-6(1H)-one (52 mg, 0.15 mmol), propane-1-sulfonamide (46 mg, 0.37 mmol), Pd2(dba)3 (7 mg, 5%), X-Phos (11 mg, 15%) and Cs2CO3 (68 mg, 0.21 mmol) was diluted with 1,4 dioxane (1 mL). After the mixture was purged with nitrogen for 5 min, it was sealed and heated to 90 C. for 3 hr. The cooled mixture was poured into H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by prep-HPLC (10 min_10-95% ACN_0.1% formic acid, 20 ml/min) to afford the title compound (36 mg, 55%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta 0.69-0.76 (m, 3H) 1.32-1.43 (m, 2H) 2.03-2.12 (m, 9H) 2.62-2.71 (m, 2H) 3.54 (s, 3H) 6.62 (s, 1H) 6.98 (s, 1H) 7.03-7.15 (m, 3H) 7.72 (s, 1H) 8.22 (s, 1H) 10.36 (br s, 1H). LCMS (M+H)+442.

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 24243-71-8.

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennan; (250 pag.)US2017/298040; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics