Author: tianli

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.34626-51-2, name is 5-Bromopentan-1-ol, molecular formula is C5H11BrO, molecular weight is 167.0442, as common compound, the synthetic route is as follows.Formula: C5H11BrO

e added pyridine (7.1 g, 90 mmol) and benzoyl chloride (10.2 g, 72.5 mmol) at 0 oC. The resulting mixture was stirred for 3 h at room temperature under nitrogen atmosphere. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with 1% ethyl acetate in petroleum ether to afford 5-bromopentyl benzoate (12.5 g, 77%) as a colorless oil. 1H NMR (400 MHz, CDCl3) d 8.07 (dd, J = 8.4, 1.5 Hz, 2H), 7.62-7.53 (m, 1H), 7.46 (dd, J = 8.4, 7.0 Hz, 2H), 4.36 (t, J = 6.5 Hz, 2H), 3.46 (t, J = 6.7 Hz, 2H), 1.96 (p, J = 7.0 Hz,2H), 1.82 (dt, J = 8.3, 6.5 Hz, 2H), 1.64 (dddd, J = 14.8, 9.5, 6.6, 3.5 Hz, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,34626-51-2, 5-Bromopentan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); A1;,
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Synthetic Route of 722-92-9, 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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol. A new synthetic method of this compound is introduced below.

To a suspension [OF 2- (4-AMINOPHENYL)-1,] 1,1, 3,3, 3-hexafluoropropan-2- ol (Oakwood, 8.4 g, 28.4 [MMOL)] in CH2CI2 (75 mL) was added trifluoroacetic anhydride (4.4 mL, 31.2 [MMOL)] via addition funnel over 30 min. After stirring at ambient temperature overnight, the reaction mixture was diluted with ethyl acetate and washed with water, saturated NaHCO3, and brine. The organics were dried [(MGS04),] filtered and concentrated to afford the intermediate amide as a white solid. The amide was dissolved in anhydrous THF (75 mL) and lithium aluminum hydride [(1 M SOLUTION] in THF, 75 mL) added over 30 min. After stirring at ambient temperature for 30 min, the solution was heated at reflux over 18 h. The reaction mixture was cooled to room temperature and quenched under argon with ethyl acetate. Water was carefully added and the resulting mixture stirred 30 min. The mixture was filtered through a pad of celite and the filtrate concentrated in vacuo. The resulting oil was dissolved in ethyl acetate and washed several times with brine. The organics were dried [(MGS04)] and concentrated to afford the title compound as a yellow oil (5.6 g, 58percent). MS (ES+) m/z 342 [(MH+).]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,722-92-9, 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA CORPORATION; WO2003/99769; (2003); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33420-52-9, name is 2,2-Difluoropropan-1-ol, molecular formula is C3H6F2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Product Details of 33420-52-9

To a solution of 2,2-difluoropropan-1-ol (1.30 g) in THF (25 mL) was added 60% sodium hydride (0.64 g) at0C, and the mixture was stirred at the same temperature for 20 min. To the reaction mixture was added methyl 4,6-dichloropyrimidine-5-carboxylate (2.55 g), and the mixture was stirred under an argon atmosphere at 0C for 1 hr. Thereaction mixture was diluted with ethyl acetate, and the organic layer was washed with saturated brine, and dried overanhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography (ethyl acetate/hexane) to give the title compound (2.81 g).1H NMR (300 MHz, DMSO-d6) delta 1.70 (3H, t, J = 19.2 Hz), 3.92 (3H, s), 4.77 (2H, t, J = 12.8 Hz), 8.84 (1H, s).

With the rapid development of chemical substances, we look forward to future research findings about 33420-52-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; SHIMOKAWA, Kenichiro; KOJIMA, Takuto; SAKAMOTO, Hiroki; FUJIMORI, Ikuo; NAKAMURA, Minoru; YAMADA, Masami; MURAKAMI, Masataka; KAMATA, Makoto; SUZUKI, Shinkichi; (78 pag.)EP3144308; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29683-23-6, Tetrahydro-2H-thiopyran-4-ol, 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, 29683-23-6, blongs to alcohols-buliding-blocks compound. Application In Synthesis of Tetrahydro-2H-thiopyran-4-ol

Step A. (l SJaS,6aR)-4-((2-fluoro-5-[2-methyl-6-(tetrahydro-2 H-thiopyran-4-yloxy)pyridin-3- yllbenzyl} oxy)- 1 , 1 a,6,6a-tetrahydrocvcloproparalindene- 1 -carboxylic acid To a solution of tetrahydro-2H-thiopyran-4-ol (56.6 mg, 0.48 mmol) in DMF (2 ml) at 0 C was added sodium hydride (60%, 19.2 mg, 0.48 mmol). The reaction mixture was stirred at 0 C for approximately 30 mins. (l S,laS,6aR)-4- {[2-fluoro-5-(6-fluoro-2-methylpyridin-3- yl)benzyl]oxy}- l, la,6,6a-tetrahydrocyclopropa[a]indene-l-carboxylic acid, ethyl ester from Example 1, Step B (100 mg, 0.24 mmol) was added to the reaction. The mixture was stirred at room temperature overnight. 1 ml of LiOH(lM) was added to the reaction and irradiated microwaves at 100 C for 1 hour. The pH of the mixture was adjusted to 7.0 with 1 N HCl. The residue was purified by preparative HPLC reverse phase (C-8), eluting with Acetonitrile/Water with 0.1 % of TFA to give the title compound. MS: m/e 488.1 (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,29683-23-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); A1;; ; Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; LI, Bing; SZEWCZYK, Jason, W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi, P.; PIO, Barbara; DANG, Qun; LIN, Linus, S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/95256; (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. 2566-44-1, name is 2-Cyclopropylethanol. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 2566-44-1

General procedure: Diisopropylamine(0.3ml, 1.8mmol)was added to a solution of cyclopropanol (0.1ml, 1.8mmol) and triphosgene(267mg, 0.9mmol) in dichloromethane which was cooled to 0 and stirred for 1 hour at room temperature. 3-Amino-5-((2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)ethynyl)benzoate(Step 2 of example 8)(100mg, 0.18mmol) and diisopropylethylamine(0.12ml, 0.54mmol) was added to the reaction mixture and stirred for 3 hours at room temperature. Water was added to the reaction mixture and the product was extracted into dichloromethane. The combined organic layers were dried over MgSO 4, filtered, evaporated in vacuum and purified using silica chromatography to afford the intermediate compound methyl3-((2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)ethynyl)-5-((cyclopropoxycarbonyl)amino)benzoate(35mg, 30%). [1627] 1H-NMR (CDCl 3, 400MHz): delta 7.96 (m, 1H), 7.84 (m, 2H), 6.86 (d, 1H), 6.69 (dd, 1H), 7.42-7.31 (m, 4H), 6.86 (d, 1H), 6.72 (dd, 1H), 5.64 (s, 2H), 4.82 (s, 2H), 3.92 (s, 3H), 2.16 (m, 1H), 1.31-1.14 (m, 4H).

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, 2566-44-1, 2-Cyclopropylethanol.

Reference:
Patent; IL DONG PHARMACEUTICAL CO., LTD.; KANG, Jae-Hoon; LEE, Hong-Sub; LEE, Yoon-Suk; JEONG, Jin-Ah; KWON, Sung-Wook; KIM, Jeong-Guen; KIM, Kyung-Sun; SONG, Dong-Keun; PARK, Sun-Young; KIM, Kyeo-Jin; CHOI, Ji-Hye; HWANG, Hey-Min; (170 pag.)WO2018/190643; (2018); A1;,
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Application of 622-93-5, Adding some certain compound to certain chemical reactions, such as: 622-93-5, name is 3-(Diethylamino)propan-1-ol,molecular formula is C7H17NO, 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 622-93-5.

Reference Example 14 3-(Diethylamino)propyl 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chlorobenzyl)-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]pyridine-6-carboxylate [Show Image] A solution of the compound of Reference Example 17 (100 mg), 3-diethylamino-1-propanol (45 muL), 1-hydroxybenzotriazole (40 mg), 1-ethyl-3-(dimethylaminopropyl)carbo-diimide hydrochloride (50 mg) and triethylamine (84 muL) in N,N-dimethylformamide (2 mL) was stirred at 25C for 16 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (developing solvent: chloroform/methanol = 20/1) to obtain the title compound (27 mg) as a white amorphous substance. MS (ESI+) 615 (M++1, 100%).

According to the analysis of related databases, 622-93-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1690863; (2006); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 456-47-3, name is 3-Fluorobenzyl alcohol, molecular formula is C7H7FO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Product Details of 456-47-3

General procedure: The product analysis was carried out under kinetic conditions. In a typical experiment, benzyl alcohol(0.1 mol), TsOH (1.0 mol) and BIDC (0.02 mol) were made up to 50 ml in DMSO and kept in the dark for ca. 12 h to ensure completion of the reaction. The solution was then treated with excess (200 ml) of a saturated solution of 2,4-dinitrophenylhydrazine in 2 mol dm3 HCl and kept overnight in a refrigerator. The precipitated 2,4-dinitrophenylhydrazone(DNP) was filtered off, dried, weighed, recrystallized from ethanol, and weighed again. The yields of DNP before and after recrystallization were 7.89 g (92%) and 6.86 g (80%)respectively, indicating the amount of benzaldehyde formed is about 3.0-3.1 g. The DNP was found identical (m.p. andmixed m.p.) with the DNP of benzaldehyde. The identity of the DNP was confirmed by the elemental analysis also. The observed values were C, 54.79%; H, 3.40% and N, 19.39%,the calculated values for C13H10N4O4 are C, 54.55%; H,3.50% and N, 19.58%. In similar experiments, with the other substituted benzyl alcohols the yields of DNP, after recrystallization, were in the range of 75 88%. CrVI is reduced to CrIII.

With the rapid development of chemical substances, we look forward to future research findings about 456-47-3.

Reference:
Article; Kothari, Seema; Kumar, Pravesh; Panday, Dinesh; Journal of the Indian Chemical Society; vol. 95; 10; (2018); p. 1207 – 1215;,
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Synthetic Route of 10488-69-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 10488-69-4, name is Ethyl 4-chloro-3-hydroxybutanoate, molecular formula is C6H11ClO3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The compound B obtained in Example 1 was dissolved in 200 ml of dichloromethane, was added sodium carbonate (37.2 g, 0.35 mol) the reaction solution was cooled to 0 to 5 ° C, acetyl chloride (23.5 g, 0.30 mol) was added dropwise,I insulation reaction 5h, after adding 200 ml of water, the organic layer was washed with water and then with saturated brine, dried and filtered. The solvent was distilled off under reduced pressure to obtain 53.5 g (0.256 mol) of the crude product of Compound C, the molar yield was 95percent.

According to the analysis of related databases, 10488-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Yang, Yong; Qiao, Zhitao; Chen, Anfeng; Zhou, Bingcheng; Liu, Bingxian; Zhou, Junan; Ge, Xu; (10 pag.)CN105566242; (2016); A;,
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Synthetic Route of 52059-53-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.52059-53-7, name is 2-(3-Fluorophenyl)ethanol, molecular formula is C8H9FO, molecular weight is 140.1549, as common compound, the synthetic route is as follows.

General procedure: To a solution of 2-(4-fluorophenyl)ethan-1-ol (1.12g, 7.99mmol) in DCM (45mL) at 0C was added imidazole (0.60g, 8.8mmol), triphenylphosphine (2.31g, 8.80mmol), and iodine (2.03g, 8.00mmol) in rapid succession. The mixture was allowed to stir at 0C for 10min before being gradually warmed to room temperature and let stir an additional 3h. Once TLC confirmed complete conversion the reaction was quenched with saturated aqueous Na2S2O3 (90mL) and the resulting solution extracted with DCM (3×30mL). The resulting organics were dried over MgSO4 and concentrated in vacuo. The resulting white solid was resuspended in 100mL hexanes and filtered to remove the byproduct triphenylphosphine oxide as a white precipitate. Following filtration the crude material was purified using Teledyne ISCO Combi Flash system (40g column, solid loading on silica, 100% hexanes, 20min run) to afford 1-fluoro-4-(2-iodoethyl)benzene (1.43g, 72%) as a clear oil.

The chemical industry reduces the impact on the environment during synthesis 52059-53-7, I believe this compound will play a more active role in future production and life.

Reference:
Article; Jeffries, Daniel E.; Witt, Jonathan O.; McCollum, Andrea L.; Temple, Kayla J.; Hurtado, Miguel A.; Harp, Joel M.; Blobaum, Anna L.; Lindsley, Craig W.; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5757 – 5764;,
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Synthetic Route of 33893-85-5, 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 33893-85-5 as follows.

EXAMPLE 5 To acetic acid in which Ce (IV)/PFCP (50 mg, 0.027 mmole) and 200 mg of NaBrO3 were dispersed and dissolved, 1.0 mmole of 1,10-undecane diol and 1.0 mmole of 4-hydroxymethyl cyclohexanol were added, respectively. The reaction mixture was heated for three hours at 55 C. and the product was purified with a column chromatography to yield 154 mg (82% yield) of 10-undecane-1-ol and 93 mg (73% yield) of 4-hydroxymethyl cyclohexanone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33893-85-5, its application will become more common.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4617153; (1986); A;,
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