Tag: M.W=100-200

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.495-76-1, name is Benzo[d][1,3]dioxol-5-ylmethanol, molecular formula is C8H8O3, molecular weight is 152.1473, as common compound, the synthetic route is as follows.Computed Properties of C8H8O3

General procedure: In a typical reaction, the catalyst was weighed into a screw-capped glass pressure vessel containing a stir bar. The required amounts of alcohol (0.5 mmol) and amine (0.6 mmol), pre-dissolved in solvent (2 mL), were added and the vessel was filled with oxygen, sealed, and heated to the desired temperature in an oil bath with stirring. The products of the reaction were analyzed by gas chromatography (GC, Agilent 7890A) and GC-mass spectrometry (MS, Agilent 7890A/5975C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,495-76-1, Benzo[d][1,3]dioxol-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Zhixin; Wang, Yehong; Wang, Min; Lue, Jianmin; Li, Lihua; Zhang, Zhe; Li, Mingrun; Jiang, Jingyang; Wang, Feng; Chinese Journal of Catalysis; vol. 36; 9; (2015); p. 1623 – 1630;,
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Reference of 6920-22-5, Adding some certain compound to certain chemical reactions, such as: 6920-22-5, name is Hexane-1,2-diol,molecular formula is C6H14O2, 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 6920-22-5.

General procedure: Glycerol (0.3 mmol, 42 mg), NH4ReO4 (0.03 mmol, 8 mg), 2,4-dimethyl-3-pentanol (0.43-0.86 mmol, 60-120 muL), and 1 mL anhydrous toluene were added to a thick-walled Ace glass reactor tube. The Teflon seal was closed and the reactor was placed in a heating mantle connected with a Digi Troll (Glas-Col) digital temperature controller equipped with a thermocouple at 140-165 C for 5-48 h while stirring. After cooling to room temperature, the solution was filtered to remove the precipitated NH4ReO4 and analyzed with GC-MS

According to the analysis of related databases, 6920-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gossett, Justin; Srivastava, Radhey; Tetrahedron Letters; vol. 58; 39; (2017); p. 3760 – 3763;,
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Application of 5456-63-3, 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.5456-63-3, name is trans-2-Aminocyclohexanol hydrochloride, molecular formula is C6H14ClNO, molecular weight is 151.6345, as common compound, the synthetic route is as follows.

To a suspension of l-(2,4-dichlorophenyl)-4-hydroxymethyl-5-[4-(3,3,3-trifluoropropane- l-sulfonyloxy)phenyl]-lH-pyrazole-3-carboxylic acid (0.70 g, 1.30 mmol) in dichloromethane (90 ml) was added c-2-aminocyclohexanol hydrochloride (200 mg, 1.32 mmol) followed by triethylamine (0.37 ml, 2.63 mmol) and BOP (708 mg, 1.60 mmol). The reaction mixture was stirred at room temperature overnight, poured into ice- water and extracted with EtOAc (x3). The combined organic extracts were dried (Na2SO4), filtered and concentrated. Flash chromatography (heptane : EtOAc 50 : 50 – EtOAc) and CH2Cl2 : MeOH 99 : 1 – 95 : 5) afforded 200 mg (24%) of the title compound as a colorless solid. HPLC: 89%. MS: 658 (M+Na).

The chemical industry reduces the impact on the environment during synthesis 5456-63-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/148061; (2007); A1;; ; Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/148062; (2007); A1;,
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Application of 4152-92-5, 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. 4152-92-5, name is (2-(Aminomethyl)phenyl)methanol, molecular formula is C8H11NO, 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.

Example 1(3R,6f?)-3-(2,3-Dihydro-1 H-inden-2-yl)-6-(1 -ethylpropyl)-1 -[2(hydroxymethyl)- benzyI]piperazine-2,5-dione [2-(Aminomethyl)phenyl]methanol (4.12g, 30 mmol) was dissolved in methanol (30ml) and 2-ethylbutanal (3.7ml, 30 mmol) added followed by (2R)-2,3-dihydro-1H-inden-2- yl({[(1 ,1-dimethylethyl)oxy]carbonyl}amino)ethanoic acid (8.74g, 30 mmol). The mixture was stirred for 15 minutes before 4-chlorophenylisonitrile (4.13g, 30 mmol) was added. The mixture was stirred for 2.25 hours and then left to stand at room temperature overnight (16.3 hours) before it was cooled in an ice / water bath. Then acetyl chloride (12.75ml, 179.5 mmol) was added dropwise, keeping the reaction temperature below 200C. Then the mixture was stirred in the cooling bath for a further 10 minutes before it was stirred at room temperature. After 5 hours the mixture was evaporated under reduced pressure to leave a dark brown gum. The gum was stirred in chloroform (75ml) and saturated aqueous sodium bicarbonate solution (75ml) for 20 minutes before it was diluted with chloroform (75ml) and the phases separated. The aqueous phase was extracted with chloroform (3 * 75ml). The combined organic phase was dried (MgSO4) and concentrated under reduced pressure to ca. 75ml. The chloroform solution was treated with glacial acetic acid (3ml) and left to stand, at room temperature over the weekend. Then the reaction mixture was washed with 2M hydrochloric acid (75ml), followed by saturated aqueous sodium bicarbonate solution (75ml). The organic phase was dried (MgSO4) and evaporated under reduced pressure and dried to leave a brown foam. The foam was loaded in dichloromethane onto a 33Og flash silica chromatography column (pre-eluted with 20% ethyl acetate in cyclohexane). The column was eluted with 20% to 100% ethyl acetate in cyclohexane to afford (3f?,6R)-3-(2,3-dihydro-1H-inden-2- yl)-6-(1-ethylpropyl)-1-[2-(hydroxymethyl)benzyl]piperazine-2,5-dione (4.12g) as a pale brown solid. HPLC (A) Rt = 3.26 minutes; m/z [M+H]+ = 421. EPO 1H NMR (CDCI3) delta 7.37 (m, 1 H), 7.30 (m, 2H), 7.21 (m, 5H), 6.84 (br d,1 H), 5.45 (d, 1 H), 4.74 and 4.63 (d, 2H), 4.16 (d, 1 H), 4.08 (dd, 1 H), 4.04 (d, 1 H), 3.15 (m, 3H), 2.92 (m, 1H), 2.78 (m, 2H), 1.76 (m, 1 H), 1.62 (m, 3H), 1.31 (m, 1 H), 0.92 (m, 6H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 4152-92-5, (2-(Aminomethyl)phenyl)methanol.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/67462; (2006); 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. 4464-18-0, name is Benzene-1,3,5-triyltrimethanol. A new synthetic method of this compound is introduced below., name: Benzene-1,3,5-triyltrimethanol

1 ,3,5-Tris(hydroxymethyl)benzene 15 (927 mg, 5.12 mmol) was suspended in CH2CI2 (25 mL) and solid PCC (5.94g, 27.6 mmol) was added. After 30 minutes of stirring, the reaction was diluted with acetone (10 mL) and was allowed to stir for 3 hr at RT. TLC (10% MeOH, 90% CH2CI2 Rf=0.50) was used to determine if the reaction was complete. After the reaction was complete, the precipitated chromium salts were filtered off and washed with CH2CI2. The aqueous layer was extracted 3 times in CH2CI2 and saturated Na2CO3. The organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated. Flash column chromatography (100% CH2CI2 Rf=0.4) gave 16 (272 mg, 1.68 mmol, 33%). 1H NMR (CDCI3): delta 10.21 (s, 3H), 8.63 (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, 4464-18-0, Benzene-1,3,5-triyltrimethanol.

Reference:
Patent; UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.; PHANSTIEL, Otto; ARCHER, Jennifer, J.; WO2010/148390; (2010); A2;,
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Electric Literature of 86770-74-3 , The common heterocyclic compound, 86770-74-3, name is 2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethanol, molecular formula is C8H19NO4, 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.

To a solution of 1-7 and HATU (147 mg) in DMF (1 mL) was added dropwise DIEA (135 muL) and tetraethylene glycol monoamine (45 muL). After stirring at room temperature for 5 h, the reaction was quenched by 10% aqueous citric acid, and the reaction mixture was extracted with EtOAc. The organic phase was washed with 1N HCl, brine, and saturated NaHC03. After drying over MgSO4 and filtration, solvent was removed with a rotary evaporator, and the mixture was purified by silica gel chromatography (DCM: MeOH=30: 1) to afford 1-27 in 70% yield. Q-TOF LC/MS m/z 609.3797 [M+H]+ (calcd. 608.37 for C32H52N2O9 [M]+); 1HNMR (400 MHz, CDCl3) delta -0.45 (1H, m), 0.685 (1H, m), 0.825 (6H, m), 1.13 (9H, s), 1.27-1.64 (6H, m), 1.94 (1H, m), 2.05 (1H, m), 2.64 (2H, m), 3.38-3.91 (16H, m), 4.07 (1H, t, J=8 and 12 Hz ), 4.25 (1H, m), 4.99 (1H, m), 6.35-7.06 (4H, aromatic H); 13C NMR (100 MHz, CDC13) delta 21.45, 24.12, 25.92, 28.20, 30.00, 31.10, 38.40, 39.51, 40.65, 49.28, 50.18, 52.77, 61.65, 69.98, 70.22, 70.60, 70.90, 72.60, 73.92, 80.30, 120.40, 123.35, 129.95, 132.23, 132.46, 159.12, 171.62, 173.23, 174.34.

The synthetic route of 86770-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; THE UNITED STATES OF AMERICA as represented by THE DEPARTMENT OF VETERANS AFFAIRS; SADEGHI, Mehran; YE, Yunpeng; KIM, Hye-Yeong; HUANG, Henry (Yiyun); TOCZEK, Jakub; (85 pag.)WO2017/177144; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 702-98-7, 2-Methyladamantan-2-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, Safety of 2-Methyladamantan-2-ol, blongs to alcohols-buliding-blocks compound. Safety of 2-Methyladamantan-2-ol

A reactor made of glass and equipped with a stirrer was charged with 9 L of toluene, 950 g of 2-methyladamantanol, 50 g of methacrylic acid and 5.3 g of cresol sulfonic acid. The resulting mixture was heated until the reflux of toluene occurred, followed by reflux for 2 hours while distilling off water, whereby 2-methyleneadamantane was prepared. After it was cooled to 50 C. and 8 L of toluene was distilled off from it under reduced pressure, the residue was cooled to 0 C. A methacrylate forming reaction was then caused by adding 1280 g of methacrylic acid and 83 g of boron trifluoride ethyl ether and stirring the resulting mixture for one hour. After the reaction mixture was washed with 6 L of a 10% aqueous sodium carbonate solution and 5 L of deionized water, toluene was distilled off at 70 C. under reduced pressure, whereby 1126 g of crude 2-methyladamantan-2-yl methacrylate was obtained. The resulting product contained 91.3 wt. % of 2-methyladamantan-2-yl methacrylate and 7.9 wt. % of 2-methyleneadamantane. The crude 2-methyladamantan-2-yl(meth)acrylate (100 g) thus obtained and 50 g of n-undecane (boiling point under atmospheric pressure: 194.5 C., coagulation point: -25.6 C., solubility of methyleneadamantane in 100 g of n-undecane at 0 C.: 101 g) were distilled at 60 C. and 1 mmHg by using a vacuum still and 61 g was distilled off in 60 minutes. The fraction thus distilled off contained 86% of 2-methyleneadamantane together with undecane. The distillation temperature was raised to 85 C. and 3.5 g was distilled off further in 10 minutes to adjust the amount of 2-methyleneadamantane remaining in the still to less than 1 wt. %. The residue in the still was then distilled at 125 C. and 1 mmHg, whereby 81.2 g of 2-methyladamantan-2-yl(meth)acrylate having a purity of 99.5 wt. % was obtained. The resulting product had a 2-methyleneadamantane content of 0.1 wt. %.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,702-98-7, 2-Methyladamantan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Chemical Corporation; US2008/51597; (2008); 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. 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, 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. SDS of cas: 39590-81-3

Thionyl chloride (3 mL, 42.2 mmol) was added dropwise to a solution of 6-bromo-2-(4-chloro-2- (methylsulfonyl)benzyl)-3-(4-chlorophenyl)-4-fluoro-3-hydroxyisoindolin-1 -one (Example 35, Step 4 ) (4.72 g, 8.44 mmol) in THF (50 mL) at 0 C under a nitrogen atmosphere. DMF (20 drops) were added and the orange solution was allowed to warm to rt over 1 d. The reaction mixture was concentrated in vacuo and dissolved in THF (40 mL). Cyclopropane-1 ,1 -diyldimethanol (1 .72 g, 16.9 mmol) was added followed by K2C03 (2.33 g, 16.9 mmol) and the orange mixture was stirred at rt under an atmosphere of nitrogen for 1 d. DCM and water were added and the layers separated. The aqueous layer was extracted with DCM and the combined organic layers were dried (phase separator) and concentrated in vacuo. The residue was purified by Biotage (30 – 35% EtOAc in iso-hexanes) to give the title compound (3.33 g, 61 %) as a pale yellow solid. NMR (400 MHz, DMSO) 8.01 (1 H, d), 7.95 (1 H, dd), 7.79 (1 H, d), 7.56 (1 H, dd), 7.36 (2H, d), 7.30 – 7.26 (3H, m), 5.01 – 4.90 (2H, m), 4.45 (1 H, t), 3.48 – 3.31 (2H, m), 3.29 (3H, s), 3.05 – 2.96 (2H, m), 0.42 – 0.40 (2H, m), 0.27 (1 H, d), 0.19 (1 H, dd).

With the rapid development of chemical substances, we look forward to future research findings about 39590-81-3.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); 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. 2807-30-9, name is 2-Propoxyethanol, the common compound, a new synthetic route is introduced below. name: 2-Propoxyethanol

Compound 2 (100 mg,0.15 mmol) was treated with 30% HBr/acetic acid (5 ml), and theresulted solution was stirred at room temperature for 2 h. Severaltypes of alcohol (50 ml) were added to the solution, and themixture was stirred at 30e80 C for 4 h under N2 protection. Then50 mL of DCM was added and separated, the combined organiclayers were washed with water (3 50 mL). The solvent wasevaporated and the residue was dissolved in THF (5 mL). Theresulted solution was treated with 1M LiOH (0.75 mL, 0.75 mmol),and the resulting mixture was stirred at room temperature for1e2 h. 1 M HCl solution was added to the mixture until pH 3 wasattained. Then the suspensionwas extracted with DCM (3 50 mL).The combined organic layers were washed with water (3 50 mL)and dried over anhydrous Na2SO4. The organic solvent wasremoved under reduced pressure and the residue was purified bycolumn chromatography over silica gel to afford black solid 5e13.

The synthetic route of 2807-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Dan-Ye; Chen, Zhi-Long; Gao, Ying-Hua; O’Shea, Donal F.; Wu, Dan; Wu, Xiao-Feng; Yan, Yi-Jia; Zhu, Wei; Zhu, Xue-Xue; European Journal of Medicinal Chemistry; vol. 187; (2020);,
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Reference of 180205-28-1, 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. 180205-28-1, name is 1-(Aminomethyl)cyclobutanol, molecular formula is C5H11NO, 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.

5-[4-Fluoro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-1,3,4-oxadiazin-2-one (320 mg, 1.22 mmol, Intermediate 66) was dissolved in DMSO (2.0 ml), and 1 – (aminomethyl)cyclobutan-l -ol (247 mg, 2.44 mmol) was added. The mixture was stirred at 100 “C overnight. The reaction mixture was dilut ed with DMSO, filtered and purified by preparative HPLC to give 231 mg (95 % purity, 52 % yield) of the title compound. LC-MS (Method 1): Rt = 1.00 min; MS (ESIpos): m/z = 344 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.546 (0.74), 1.569 (1.05), 1.591 (0.73), 1.637 (0.72), 1.644 (0.54), 1.654 (0.80), 1.665 (0.53), 1.976 (4.50), 1.993 (4.03), 1.998 (5.17), 2.015 (2.05), 2.074 (14.34), 2.518 (1.22), 2.522 (0.84), 3.279 (4.02), 3.291 (4.05), 5.278 (1.45), 5.308 (16.00), 5.527 (3.57), 7.000 (2.21), 7.022 (2.34), 7.746 (3.95), 7.752 (2.30), 7.774 (1.55), 7.779 (1.23), 10.898 (5.51).

According to the analysis of related databases, 180205-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; ELLERMANN, Manuel; GRADL, Stefan, Nikolaus; KOPITZ, Charlotte, Christine; LANGE, Martin; TERSTEEGEN, Adrian; LIENAU, Philip; HEGELE-HARTUNG, Christa; SUeLZLE, Detlev; LEWIS, Timothy, A.; GREULICH, Heidi; WU, Xiaoyun; MEYERSON, Matthew; BURGIN, Alex; (500 pag.)WO2019/25562; (2019); A1;,
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