Month: August 2021

Related Products of 929-75-9, These common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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.

0.500 g of cinnamic acid, 0.295 g of 1,11-diamino-3,6,9-trioxadecane, 0.647 g of EDCI, 0.037 g of DMAP, 10 mL of anhydrous dichloromethane were sequentially added to the round bottom flask, and stirred at room temperature. After 12 h, 20 mL of dichloromethane was added, and the mixture was washed successively with brine (1×30 mL) and water (2×30 mL), dried over anhydrous sodium sulfate, filtered, evaporated to dryness Chloroform/methanol = 35:1; 50:4) gave 0.178 g of a pale yellow oily substance, yield 28% (see Figure 49 for the synthetic route and Figure 50 for the characterization)

Statistics shows that 1,11-Diamino-3,6,9-trioxaundecane is playing an increasingly important role. we look forward to future research findings about 929-75-9.

Reference:
Patent; Chinese Academy Of Medical Sciences Biomedical Engineering Institute; Liu Tianjun; Wang Jiawen; Li Guoliang; Hong Ge; Wang Wenzhi; (37 pag.)CN110229110; (2019); A;,
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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. 458-50-4, name is 4-Bromo-3-fluoroanisole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluoroanisole

A mixture of tert-butyl ((3S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1-(5-(2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamido)-1H-indol-4-yl)pyrrolidin-3-yl)carbamate (50 mg, 0.072 mmol), 1-bromo-2-fluoro-4-methoxybenzene (22.3 mg, 0.109 mmol), copper(I) iodide (2.1 mg, 10.9 mumol) and potassium phosphate, tribasic (32.3 mg, 0.152 mmol) was purged with N2 and treated with N,N-dimethylcyclohexane-1,2-diamine (6.2 mg, 0.043 mmol) in 0.5 mL toluene. The reaction mixture was further treated with 0.3 mL DMF and heated to 110 C. for 40 hrs. After cooling to r.t., the reaction mixture was diluted with water and EtOAc. The separated organic phase was washed with brine, dried over sodium sulfate and concentrated under vacuum. The crude product was dissolved in 1 mL THF and treated with 0.5 mL of TBAF solution (1.0 M in THF). The resulting mixture was stirred at r.t. for 1 hr, then diluted with water and EtOAc. The separated organic phase was washed with brine, dried over sodium sulfate and concentrated under vacuum. The crude was purified by flash chromatography (eluted with EtOAc) and the obtained product was then dissolved in 1 mL DCM and treated with 1 mL TFA. The resulting mixture was stirred at r.t. for 1 hr and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C32H31F2N6O4 (M+H)+: m/z=601.2; found 601.4.

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 458-50-4.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Nguyen, Minh; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Qinda; Yao, Wenqing; (72 pag.)US2019/315717; (2019); A1;,
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Electric Literature of 2674-34-2,Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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 solution of compound Q-9 (5.0 g, 16.77 mmol) in CH3CN (50 mL) was heated to 100 0C, followed by the addition of a solution of eerie ammonium nitrate (CAN, 14 g, 25.54 mmol) in water (75 mL) over a period of 30 min. The reaction mixture was then allowed to cool to room temperature and stirred for another 30 min. The resulting precipitate was filtered, washed with water (20 mL), and dried under high vacuum to furnish compound Q-10 (2.6 g, 58%) as a yellow solid. TLC Rf = 0.4 (petroleum ether – EtOAc, 9:1); MS (ES) mlz 266 (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 1,4-Dibromo-2,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; DJABALLAH, Hakim; ANTCZAK, Christophe; WO2010/129049; (2010); A1;,
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Application of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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 5-chloro-2-ethylpyrazolo[1,5-a]pyridine-3-carboxylic acid or 2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (1.34mmol) in DMF (20mL) was added EDCI (0.39g, 2.01mmol), HOBt (91mg, 0.67mmol) and Et3N (0.68g, 6.7mmol) at room temperature. After 1h of stirring, 1a-8a (1.34mmol) was added and the reaction was heated to 80C for overnight. The mixture was cooled, and diluted with EA (50mL), washed with water and brine, dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography to afford the title compounds1-8.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Xiaoyun; Tang, Jian; Cui, Shengyang; Wan, Baojie; Franzblauc, Scott G.; Zhang, Tianyu; Zhang, Xiantao; Ding, Ke; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 41 – 48;,
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Synthetic Route of 2062-98-8, 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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2; Example 2-1; [0175] Example for Preparation of CH2CHCH(OCH3) CH2OCOCF (CF3)OCF2CF2CF3; [0176] CH2CHCH(OCH3)CH2OH (270 g) was charged together with NaF (334 g) into a 2 L pressure resistant reactor equipped with a reflux condenser in which a coolant at 20 C. circulated, and stirred at -10 C. While discharging by-product HF formed by the reaction out of the system from the reflux condenser on the upper portion by bubbling nitrogen gas to the reactor, FCOCF(CF3)OCF2CF2CF3 (1055 g) was dropwise added over a period of 1.5 hours. At this time, the temperature was adjusted so that the internal temperature of the reactor would be at most 0 C. After completion of the dropwise addition, stirring was carried out at 30 C. for 18 hours and then the reaction was terminated. [0177] NaF contained in the crude liquid after completion of the reaction was collected by filtration to obtain a crude product (981 g) (yield 86.4%). As a result of the analysis by NMR, the above-identified mixture was obtained as a liquid mixture with FCOCF(CF3)OCF2CF2CF3. The results of analysis of the above-identified compound are as follows. [0178] 1H-NMR(300.4 MHz, solvent:CDl3, standard:TMS) delta (ppm):3.29(s, 3H), 3.85-3.90(m, 1H), 4.24-4.45(m, 2H), 5.34(s, 1H), 5.39(d,J=8.4 Hz, 1H), 5.59-5.71(m, 1H). [0179] 19F-NMR(282.7 MHz, solvent:CDCl3, standard:CFCl3) delta (ppm): -81. 8(3F), -82.6(3F), -79.9-87.5(2F), -130.2(2F), -132.3(1F).

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, Perfluoro(2-methyl-3-oxahexanoyl) fluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASAHI GLASS COMPANY LIMITED; US2003/216595; (2003); A1;,
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Synthetic Route of 22483-09-6, 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 22483-09-6 as follows.

A solution of aminoacetaldehyde dimethyl acetal (25 mL, 229 mmol) in toluene (120 mL) is treated at 0 C with a 4.85 M sodium hydroxide solution (70.8 mL, 343.5 mmol). The mixture is stirred at 0 C for 10 minutes and benzyl chloroformate (33.8 mL, 229 mmol) is added keeping the internal temperature below 20 C during the addition. The mixture is warmed to room temperature over 4 hours. The organic layer is separated, washed with brine, dried over sodium sulfate, and concentrated to dryness to give the title compound (54 g, 98 %). ES/MS (m/e): 240 (M+H).

According to the analysis of related databases, 22483-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; GREEN, Steven James; MERGOTT, Dustin James; WATSON, Brian Morgan; WINNEROSKI JR., Leonard Larry; WO2014/143579; (2014); A1;,
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Synthetic Route of 6346-09-4, A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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.

Step1 To the stirred solution of 1,3-dioxo-1,3-dihydro-isoindole-2-carboxylic acid ethyl ester (10 g, 62 mmol, 1 eq) in dry THF (200 mL) were added 4,4-diethoxy-butylamine (13.6 g, 62 mmol, 1 eq) and TEA (8.6 mL, 62 mmol, 1 eq) under ice cooled condition and stirred at RT for 16 h. After completion of the reaction, it was concentrated under reduced pressure to obtain crude product which was purified by silica gel (100-200 mesh) column chromatography (5% EA/Hexane) to afford 2-(4,4-diethoxy-butyl)-isoindole-1,3-dione (17 g, 94% yield) as light yellowish liquid.

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; JAKOB, FLORIAN; NORDHOFF, SONJA; RIDER, DAVID; WAGENER, MARKUS; BAHRENBERG, GREGOR; DUNKERN, TORSTEN; (70 pag.)US2018/78541; (2018); 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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Amino-3,3-diethoxypropane

[0080] To a stirred solution of intermediate (9) (287 mmol) in CHCl3 (2000 ml) was added 3,3-diethoxy-1-propanamine (474 mmol) at 0 C. in portions. After the addition, the reaction mixture was stirred at 0 C. for 1 hour and then at 15 C. for 2 hours. Thin Layer Chromatography (petroleum ether/ethyl acetate=5/1) showed that the reaction was completed. The reaction mixture was washed by saturated Na2SO3 aqueous (four times with 600 ml) and then saturated NaHCO3 aqueous was added until pH=7. The aqueous layer was extracted by CH2Cl2 (500 ml). The combined organic phases were washed with brine (800 ml), dried over Na2SO4 and concentrated to give the crude product. The crude product was washed by tert-butyl methylether (three times 500 ml) to give 87 g of intermediate (10) (mp. 100.8-103.8 C.).

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELANCO ANIMAL HEALTH IRELAND LIMITED; Guillemont, Jerome Emile Georges; Raboisson, Pierre Jean-Marie Bernard; Lounis, Nacer; US2013/109694; (2013); 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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., Recommanded Product: 2062-98-8

To a 3 -neck flask equipped with a temperature probe, magnetic stir bar, water- cooled condenser, and addition funnel was charged sodium borohydride (16.0 g, 423 mmol), and tetraethylene glycol dimethyl ether (125 mL). 2,3,3,3-Tetrafluoro-2- (1,1,2,2,3, 3, 3-heptafluoropropoxy)propanoyl fluoride (100 g, 301 mmol) was added dropwise to the resultant mixture. After complete addition, the reaction mixture was heated to reflux and stirred overnight. The mixture was then allowed to cool to room temperature followed by the dropwise addition of methanol (100 mL) and H2O (150 mL). The mixture was then transferred to a separatory funnel and the fluorous phase was collected and then distilled (46.1 C, 40 ton) to afford 2,3,3,3-tetrafluoro-2-(l, 1,2,2,3,3- heptafluoropropoxy)propan-l-ol (67.5 g, 71%) as a colorless liquid. The isolated compound was used in the next step. (0204) To a 3-neck flask equipped with a temperature probe, distillation head, overhead stirrer, and under N2 was charged TiCU (7.9 mL, 72 mmol). 2,3,3,3-Tetrafluoro-2- (l,l,2,2,3,3,3-heptafluoropropoxy)propan-l-ol (15.1 g, 47.8 mmol) was added dropwise with stirring and the resultant mixture was heated to 40 C followed by a 30 min stir. The mixture was then allowed to cool to room temperature followed by the dropwise addition of tetraethylene glycol dimethyl ether (45 mL). Exotherms reaching approximately 50 C were observed. The resultant mixture was allowed to warm to room temperature followed by the addition of zinc dust (9.1 g, 140 mmol) in one portion. The resultant reaction mixture was raised to 85 C. After a 3 h stir, the temperature was slowly raised to 225 C and distillate was collected with the distillation head temperature reaching 69 C affording the title compound (4.1 g, 31%) as a colorless liquid.

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; 3M INNOVATIVE PROPERTIES COMPANY; SMITH, Sean M.; LAMANNA, William M.; COSTELLO, Michael G.; BULINSKI, Michael J.; (35 pag.)WO2017/195070; (2017); 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 36805-97-7 as follows. Quality Control of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

Step C: (2Z)-1-[2-(3-Bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-fluoro-2-propen-1-one; To a solution of 1-[2-(3-bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-2-fluoroethanone (10 mg, 0.025 mmol) in DMF (2 mL) was added DMF di-tert-butyl acetal (0.85 g, 4.2 mmol) and the reaction was heated at 80 C. for 15 min. The crude reaction mixture was adsorbed to silica gel and purified by LC (5-50% EtOAc in hexanes) to give the title compound (10 mg, 88%). ESIMS (M+H)+=456.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US2008/51395; (2008); A1;,
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