Tag: M.W=200-300

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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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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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. 59767-24-7, name is 1-(4-Chlorophenyl)-1-phenylethanol. A new synthetic method of this compound is introduced below., Formula: C14H13ClO

(R)-2-[2-[1-(4-Chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine: A mixture of (R)-2-(2-chloroethyl)-1-methyl-pyrrolidine hydrochloride (0.530 g, 2.91 mmol), 1-(4-chlorophenyl)-1-phenylethanol (1.01 g, 4.39 mmol), sodium amide (0.567 g, 14.53 mmol) and toluene (10 mL) was heated at reflux for about 8 hours, cooled to ambient temperature, and filtered. The filtrate was concentrated and the resulting residue was purified by Preparative HPLC on a Kromasil C18 (30×250 mm, 10 mum) column, by eluting with acetonitrile/0.01 M ammonium acetate (3:1) at a flow rate of 42 mL/min. The racemic title compound eluted at 1.57 min. Standard extractive workup with ethyl acetate afforded the racemic title product as an oil (0.360 g, 36%).

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, 59767-24-7, 1-(4-Chlorophenyl)-1-phenylethanol.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2009/203763; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17100-58-2, (4-Bromo-2-methylphenyl)methanol, 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, 17100-58-2, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

Step 2 Methanesulfonic acid 4-bromo-2-methyl-benzyl ester; To a solution of (4-bromo-2-methyl-phenyl)-methanol (46.65 g, 0.2320 mol) in DCM (500 mL) at -150C was added mesyl chloride (20.65 mL, 0.2668 mol) followed by TEA (37.04 mL, 0.2668 mol). The reaction was stirred at -150C for 1.5 hour. A saturated solution of NH4Cl was then added at -15 0C and the resulting mixture was extracted with DCM. The EPO organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to afford methanesulfonic acid 4-bromo-2-metrryl-benzyl ester as a white solid in quantitative yield (65 g), which was used directly in step 3 without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17100-58-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/55847; (2008); A1;,
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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. 4654-39-1, name is 2-(4-Bromophenyl)ethanol, the common compound, a new synthetic route is introduced below. Formula: C8H9BrO

Production Example 4 Synthesis of 4-bromophenethyl bromide 4-Bromophenethyl alcohol (1.3 ml) was treated as in Production Example 1 to give the title compound (2.345 g) as a pale yellow oil (yield: 88.8%). 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.12(2H, t, J=7.4Hz), 3.54(2H, t, J=7.4Hz), 7.09(2H, d, J=8.4Hz), 7.45(2H, d, J=8.4Hz).

The synthetic route of 4654-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 186020-66-6, tert-Butyl 12-Hydroxy-4,7,10-trioxadodecanoate, 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, name: tert-Butyl 12-Hydroxy-4,7,10-trioxadodecanoate, blongs to alcohols-buliding-blocks compound. name: tert-Butyl 12-Hydroxy-4,7,10-trioxadodecanoate

tert-Butyl 3-(2-(2-(2-hydroxyethoxy)- ethoxy)ethoxy)propanoate [Broadpharm, 9380 Waples St., Suite 101, San Diego, CA 92121] (50 mg, 0.180 mmol, 1.00 equiv), N-(((9H-fluoren-9-yl)methoxy)- carbonyl)-O-(tert-butyl)-L-serine (69 mg, 0.180 minol, 1.00 equiv) and DMAP (22 mg, 0.180 rnrnol, 1.00 equiv) were dissolved in CH2C12 (0.9 mL) . Upon dissolution of the reagents (about 5 minutes), EDCIoHC1 (52 mg, 0.270 nirnol, 1.50 equiv) was added in one portion at room temperature, and the reaction mixture was stirred for 17.5 hours, after which it was poured into aqueous 1 N HC1 (3 mL) and EtOAc (15 niL) . The aqueous phase was extracted twice with EtOAc (5 mL), and the combined organic phases were washed with aqueous 1 N HC1 (2 mL), saturated aqueous NaHCO3 (2 mL), and saturated aqueous NaC1 (2 mL), sequentially. The organic phase was dried over Na2504, filtered and concentrated. Flash column chromatography (5i02, 5% MeOH/CH2C12) provided 95.7 mg (83%) of the title compound as a colorless oil. ?H NMR (500 MHz, DMSOd 6) 6 7.76 (d, J = 7.5 Hz, 2H), 7.63 (d, J = 7.5 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 7.40 (t, J = 7.5 Hz, 2H), 7.32 (t, J = 7.5 Hz, 2H), 5.68 (d, J = 8.5 Hz, lH), 4.54 – 4.49 (m, 1H), 4.43 – 4.21 (m, SM), 3.85 (br, iN), 3.74 – 3.57 (m, 13H) , 2.49 (t, J = 6.5 Hz, 2H), 1.44 (s, 9H), 1.16 (s, 9H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,186020-66-6, tert-Butyl 12-Hydroxy-4,7,10-trioxadodecanoate, and friends who are interested can also refer to it.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BEUTLER, Bruce; BOGER, Dale, L.; (334 pag.)WO2018/5812; (2018); A1;,
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Reference of 756520-66-8, 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. 756520-66-8, name is 1-(2,6-Dichloro-3-fluorophenyl)ethanol, molecular formula is C8H7Cl2FO, 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.

General procedure: To the solution of compound 6 (17 mg, 0.13 mmol), 3-morpholinopropan-1-ol (19 mg, 0.13 mmol) and PPh3 (51 mg, 0.19 mmol) in anhydrous THF (5 mL) was added 33 uL DEAD (0.19 mmol) dropwise. The reaction mixture was stirred at room temperature for 3h. After completion of reaction, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography using DCM: MeOH=60:1 as eluents.

According to the analysis of related databases, 756520-66-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; An, Xiao-De; Liu, Hongyan; Xu, Zhong-Liang; Jin, Yi; Peng, Xia; Yao, Ying-Ming; Geng, Meiyu; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry Letters; vol. 25; 3; (2015); p. 708 – 716;,
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Adding a certain compound to certain chemical reactions, such as: 24034-73-9, (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-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, HPLC of Formula: C20H34O, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C20H34O

N–chlorosuccinimide(1.2g,1.3equiv)wassuspendedindryCH2Cl2(15ml).Thesuspensionwascooledto–30C(acetone/liquidN2bath)andafterstirringfor5min,dimethylsulfide(750mul,1.5equiv)wasadded.Thereactionwasstirredfor10minat–30Cand10minat0C.Thenthesolutionwascooledto–40C.Asolutionofgeranylgeraniol(2g,6.9mmol)inCH2Cl2(dry,5ml)wasaddeddropwise.Theresultingsuspensionwasallowedtowarmduring150minto0C,turningintoacloudysolutionat–15C.Thereactionmixturewaspouredintopentane(150ml),Theorganiclayerwaswashedwithwater(2x50ml),brine(50ml),driedoverMgSO4andevaporated.Thereactionafforded1.94gofgeranylgeranylchlorideasacolorlessliquidwhichwasusedwithoutfurtherpurification.

The synthetic route of 24034-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jain, Samta; Caforio, Antonella; Fodran, Peter; Lolkema, Juke S.; Minnaard, Adriaan J.; Driessen, Arnold J.M.; Chemistry and Biology; vol. 21; 10; (2014); p. 1392 – 1401;,
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Reference of 307353-32-8, 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.307353-32-8, name is Methyl 3-bromo-5-(hydroxymethyl)benzoate, molecular formula is C9H9BrO3, molecular weight is 245.07, as common compound, the synthetic route is as follows.

A mixture of methyl 3-bromo-5-(hydroxymethyl)benzoate (149 mg, 0.61 mmol) and manganese(IV) oxide (529 mg, 6.08 mmol), and CH2Cl2 (3 mL) was stirred at rt overnight. The mixture was filtered through Celite and the filter cake was washed with CH2Cl2. The filtrate was concentrated to afford the title compound.

The chemical industry reduces the impact on the environment during synthesis 307353-32-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
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Synthetic Route of 23783-42-8, 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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. A new synthetic method of this compound is introduced below.

Synthesis of 2,5,8,11-tetraoxatridecan-13-ol tosylate Procedure: [0187] (JACS, 2007, 129, 13364) To a solution of 2,5,8,11-tetraoxatridecan-13-ol (7 g, 33.6 mmol) and triethylamine (4.9 ml, 35.3 mmol) in dry CH2Cl2 (100 ml), 4-toluenesulfonyl chloride (6.7 g, 35.3 mmol) and DMAP (120 mg) were added. The mixture was stirred at room temperature for 20 h. The reaction mixture was washed with 80 mL of HCl (1M) and then water. The extract was dried over anhydrous MgSO4, filtrated, and the filtrate was evaporated. The residue was used in the next step without further purification. Yield: [0188] 11.0 g (90%) NMR: [0189] 1H NMR (400 MHz, CDCl3) delta 7.75-7.64 (m, 2H), 7.31-7.26 (m, 2H), 4.16-4.06 (m, 2H), 3.62 (m 2H), 3.59-3.40 (m, 10H), 3.30 (s, 3H), 2.38 (s, 3H). [0190] 13C{1H} NMR (101 MHz, CDCl3) delta 144.75 (s), 132.90 (s), 129.77 (s), 127.8 (s), 71.82 (s), 70.60 (s), 70.48 (s), 70.47 (s), 70.41 (s), 70.39 (s), 69.23 (s), 68.55 (s), 58.90 (s), 21.53 (s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, and friends who are interested can also refer to it.

Reference:
Patent; Bergmann, Frank; Cysewski, Robert; de Cola, Luisa; Dziadek, Sebastian; Fernandez Hernandez, Jesus Miguel; Josel, Hans-Peter; Seidel, Christoph; US2015/147751; (2015); A1;,
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