Month: July 2021

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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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.30379-58-9, name is Benzyl 2-hydroxyacetate, molecular formula is C9H10O3, molecular weight is 166.17, as common compound, the synthetic route is as follows.Quality Control of Benzyl 2-hydroxyacetate

2-(Fluorenylmethoxycarbonyl)hydroxyacetic acid benzyl ester (657). To a solution of benzyl glycolate (6.0 g, 36.1 mmol) in CH2Cl2, cooled via ice-water bath, was added fluorenylmethoxy chloroformate (14 g, 1.5 equiv.) then diisopropylethylamine (9 mLs, 1.5 equiv.). After 1 hour, reaction mixture was poured into a saturated aqueaous solution of ammonium chloride and extracted with CH2Cl2, dried over Na2SO4 then concentrated in vacuo. The product was triturated from MeOH to obtain 2.2 g of 657 as a first crop of white solid. 2-(Fluorenylmethoxycarbonate) acetic acid (658). To a solution of 657 (2.2 g, 5.93 mmol) in tetrahydrofuran was added 5% Pd/C (220 mg). The resulting suspension was vigorously stirred under hydrogen atmosphere. After 90 min, the reaction mixture was filterred through Celite. The filtrate was poured into saturated aqueous NaHCO3 and washed twice with EtOAc. The aqueous layer was then acidified and the product extracted twice with CH2Cl2, dried over Na2SO4 and concentrated in vacuo to afford 1.46 g (88%) of 658 as a white solid. 2-(Fluorenylmethoxycarbonate) acetyl chloride (659), was prepared from 658 by the method used to prepare 643 to afford 659 as a crude product. (3S)-3-[(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-(2-fluorenylmethoxycarbonate)acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetylamino]4-oxo-butyric acid tert-butyl ester semicarbazone (660), was synthesised from 600b, using 659, by methods used to prepare 604d from 600b to afford 453 mg of 660. (3S)-3-[(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-(2-hydroxy)acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetylamino]4-oxo-butyric acid tert-butyl ester semicarbazone (661). A solution of 660 (423 mg) in MeOH:Et2NH (1:1, v/v) was stirred at ambient temperature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,30379-58-9, Benzyl 2-hydroxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US6204261; (2001); B1;,
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Application of 3597-91-9, Adding some certain compound to certain chemical reactions, such as: 3597-91-9, name is [1,1′-Biphenyl]-4-ylmethanol,molecular formula is C13H12O, 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 3597-91-9.

A mixture of K2CO3 (1 mmol) and the catalyst (52 mg, ?3 mol% of Pd2+) in toluene (5 ml) was prepared in a two necked flask. The flask was evacuated and refilled with pure oxygen. To this solution, the alcohol (1 mmol, in 1 ml toluene) was injected and the resulting mixture was stirred at 80 C under an oxygen atmosphere. After completion of reaction, the reaction mixture was filtered off and the catalyst rinsed twice with CH2Cl2 (5 ml). The excess of solvent was removed under reduced pressure to give the corresponding carbonyl compounds.

According to the analysis of related databases, 3597-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alizadeh; Khodaei; Kordestania; Beygzadeh; Journal of Molecular Catalysis A: Chemical; vol. 372; (2013); p. 167 – 174;,
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Synthetic Route of 63012-03-3, 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. 63012-03-3, name is (3-Chlorophenyl)(phenyl)methanol. A new synthetic method of this compound is introduced below.

To the mixture of (3-chlorophenyl)(phenyl)methanol (42.6 mg, 0.195 mmol), (cyanomethyl)trimethylphosphonium iodide (63.2 mg, 0.26 mmol) and 8-((2S,5R)-2,5- dimethylpiperazin-1-yl)-5-methyl-6-oxo-5,6-dihydro-1,5-naphthyridine-2-carbonitrile, TFA (44.6 mg, 60 %wt, 0.065 mmol) in propanenitrile (0.3 mL) was added Hunig?s base (0.114 mL, 0.65 mmol). The reaction mixture was stirred at 110 C for 5 hours. The crude material was purified via preparative LC/MS with the following conditions: (1934) Column: XBridge C18, 200 mm x 19 mm, 5 mm particles; Mobile Phase A: 5:95 acetonitrile: water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10 mM ammonium acetate; Gradient: a 0 minute hold at 50 % B, 50-90 % B over 20 minutes, then a 4 minute hold at 100 % B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS and UV signals. Fractions containing the product were combined and dried via centrifugal evaporation. The yield of diastereomeric product was 7.4 mg. Calculated molecular weight 498.03. Analytical LC/MS was used to determine the final purity. Injection 1 conditions: Column: Waters XBridge C18, 2.1 mm x 50 mm, 1.7 mm particles; Mobile Phase A: 5:95 (1935) acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 (1936) acetonitrile:water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0 %B to 100 %B over 3 min, then a 0.50 min hold at 100 %B; Flow: 1 mL/min; Detection: MS and UV (220 nm). Injection 1 results: Purity: 99.4 %; Observed Mass: 498.12; Retention Time: 2.74 min. Injection 2 conditions: Column: Waters XBridge C18, 2.1 mm x 50 mm, 1.7 mm particles; Mobile Phase A: 5:95 acetonitrile:water with 0.1 % trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile:water with 0.1% trifluoroacetic acid; Temperature: 50 C; Gradient: 0 %B to 100 %B over 3 min, then a 0.50 min hold at 100 %B; Flow: 1 mL/min; Detection: MS and UV (220 nm). Injection 2 results: Purity: 98.1 %; Observed Mass: 498.13; Retention Time: 1.83 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63012-03-3, (3-Chlorophenyl)(phenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); A1;,
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