Month: August 2021

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.107859-98-3, name is Ethyl 3-(4-(hydroxymethyl)phenyl)propanoate, molecular formula is C12H16O3, molecular weight is 208.25, as common compound, the synthetic route is as follows.name: Ethyl 3-(4-(hydroxymethyl)phenyl)propanoate

Example 3 Ethyl 3-[4-(bromomethyl)phenyl]propanoate Carbon tetrabromide (1.27 g) and triphenylphosphine (805 mg) were added to a methylene chloride solution (5 mL) of the compound (533 mg) as produced in Example 2, followed by stirring at room temperature for 30 min. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, and extraction was effected with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The resultant residue was purified on a silica gel column chromatography (n-hexane:ethyl acetate = 9:1) to give the subject title compound (667 mg) showing the following physico-chemical values: TLC: Rf 0.61 (n-hexane:ethyl acetate = 4:1); 1H-NMR (CDCl3): d 1.23, 2.61, 2.94, 4.13, 4.48, 7.18, 7.32.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107859-98-3, Ethyl 3-(4-(hydroxymethyl)phenyl)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1785421; (2007); A1;,
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Related Products of 29055-08-1, 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.29055-08-1, name is (2-(Methylamino)phenyl)methanol, molecular formula is C8H11NO, molecular weight is 137.179, as common compound, the synthetic route is as follows.

[00263] To a solution of 2-(N-methylamino)-benzylalcohol(b) (536 mg, 3.9 mmol) in dry dichloromethane (25 ml) and diisopropylethylamine (681 mul, 3.9 mmol) was added dropwise chloromethyl chloroformate (360 mul, 4.0 mmol) and the reaction mixture was stirred at 0° C. with occasional check of the reaction progress by t.l.c (n-hexane:ethyl acetate=2:1). After 2 h, the starting material disappeared on t.l.c and the solution was used directly for the following reaction. [00264] Step 2 [00265] To the reaction mixture were added diisopropylethylamine (900 mul, 5.0 mmol) and acetic anhydride (400 mg) and stirred for 3 h at ambient temperature. The reaction mixture was partitioned with dichloromethane (50 ml) and water (30 ml). The water layer was separated and extracted again with dichloromethane (50 ml). The combined organic layer was washed with brine (30 ml.x.2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting yellowish oil was purified on a column of silica gel (wakogel C-200 10 g, eluent dichloromethane_methanol=200:1) to give the title compound(c) as colorless syrup (740 mg, 70percent). EI-MS: m/z 271(M+); 1H-NMR (270 MHz, CDCl3): delta 2.10 (3H, s), 3.30 (3H, s), 5.07-5.78 (2H, br.d), 5.60 (0.8H, d, J=5.9), 5.73 (0.8H, d, J=5.9), 5.85 (0.4H, br.s), 7.16-7.23 (1H, m), 7.37-7.49 (3H, m).

Statistics shows that 29055-08-1 is playing an increasingly important role. we look forward to future research findings about (2-(Methylamino)phenyl)methanol.

Reference:
Patent; Basilea Pharmaceutica AG; US6812238; (2004); B1;,
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Related Products of 637031-88-0, 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. 637031-88-0, name is 3,3-Difluorocyclobutanol. A new synthetic method of this compound is introduced below.

: A solution of 4′-bromo-6′- fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (0809) (96.2mg, 0.2800mmol) and 2-(di-t-butylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-l,r- biphenyl (3.4 mg, 0.007 mmol) in l,4-dioxane (5.0 mL) was sparged with nitrogen for 3 mins. The reaction mixture was then treated sequentially with potassium hydroxide (47.3 mg, 0.84 mmol), water (101 pL, 5.62 mmol) and [2-(2-aminophenyl)phenyl]-methylsulfonyloxy- palladium; di-t-butyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (6.0 mg, 0.007 mmol) under continuous nitrogen stream. The vessel was sealed and heated to 80 C for 1 h and 30 min. The reaction mixture was quenched by the addition of acetic acid (64.3 pL, 1.13 mmol). The reaction mixture was poured into 75 mL of water and extracted with 4 x 20 mL EtOAc. The combined organics were dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification (87 mg). During the reaction, some of the hydrodefluorinated product formed as an impurity. Data for 6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 280. Data for l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 262.A solution of impure 6′-fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′- 5,6-dihydrocyclopenta[c]pyridine]-4′-ol (44.0 mg, 0.16 mmol), polymer supported (0812) triphenylphosphine (-2.06 mmol/g, 306.2 mg, 0.63 mmol), and 3,3-difluoro-cyclobutanol (68.1 mg, 0.63 mmol) in tetrahydrofuran (3.2 mL) was treated with diisopropyl (0813) azodicarboxylate (120 pL, 0.61 mmol) and stirred at 60 C for 2 h. The reaction mixture was filtered and the filter cake rinsed with 20 mL EtOAc. The filtrate was concentrated and purified by chromatography on silica using 10-30% EtO Ac/hexane to afford a clear solid (39.0 mg, 67%) that was a 2: 1 mixture of the fluorinated and hydrodefluorinated products. LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 352.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,637031-88-0, its application will become more common.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; JOSEY, John A.; SHRIMALI, Rajeev; WALLACE, Eli M.; WONG, Tai; (195 pag.)WO2019/191227; (2019); A1;,
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Related Products of 4152-92-5 ,Some common heterocyclic compound, 4152-92-5, molecular formula is C8H11NO, 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.

General procedure: Step i: Ketone 1 (1 mmol), primary amine 2 (1 mmol), and a mixture of Ti(Oi-Pr)4 (3.1 mg, 1.1 mol%) in 1-(trimethylsilyl)-2-pyrrolidinone (393 mg, 2.5 mmol) were heated at 70C with shaking in a sealed vial for 6 h. Step ii: After cooling down to r.t., EtOH (2 mL) was added to the solution and it was shaken until homogenization followed by the addition of NaBH4 (68 mg, 1.8 mmol). The resulting heterogeneous mixture was left staying overnight at r.t. Then, H2O (2 mL) was added and the mixture was sonicated for 2 h at r.t. to decompose the excess of NaBH4. The product was extracted with CHCl3 (3 mL), and the organic phase was washed with H2O (3 × 7 mL), dried (Na2SO4), and evaporated to give the respective secondary amine 3. Samples with purity below 95% as determined by LC-MS or 1H NMR spectroscopy were further purified by column chromatography (SiO2,eluent A: CHCl3, eluent B: i-PrOH, a linear gradient from 0% eluent B to 100% eluent B was used).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4152-92-5, its application will become more common.

Reference:
Article; Bogolubsky, Andrey V.; Moroz, Yurii S.; Pipko, Sergey E.; Panov, Dmitriy M.; Konovets, Anzhelika I.; Doroschuk, Roman; Tolmachev, Andrey; Synthesis; vol. 46; 13; (2014); p. 1765 – 1772;,
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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. 2009-83-8, name is 6-Chlorohexan-1-ol, molecular formula is C6H13ClO, 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. Computed Properties of C6H13ClO

Chlorohexanol (71.9 mmol, 10.00 g), p-nitrophenol (86.4 mmol, 11.80 g), K2CO3 (109 mmol, 15.09 g), KI (5 mg), and DMF (80 mL) were added to a three-necked flask and refluxed at 120 C.After 6 hours of reaction, samples were taken for gas chromatography.When there is no peak of 6-chloro-1-hexanol in the gas phase, the reaction is stopped, and the mixed solution is poured into a large amount of water to obtain an off-white precipitate. After drying,Recrystallization from ethanol gave p-nitrophenoxyhexanol (Intermediate A) with a yield of about 87%.The purity by HPLC analysis was 95.2%.

With the rapid development of chemical substances, we look forward to future research findings about 2009-83-8.

Reference:
Patent; Changzhou University; Xue Xiaoqiang; Liang Kang; Jiang Bibiao; Huang Wenyan; Yang Hongjun; Jiang Qimin; Jiang Li; (20 pag.)CN110343079; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 101597-25-5, 1,1-Bis(4-methoxyphenyl)prop-2-yn-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, Safety of 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, blongs to alcohols-buliding-blocks compound. Safety of 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol

A 500 mL three-necked flask equipped with a water trap was charged with 1-hydroxypyrene (Ea0,623 mg, 2.85 mmol), a propargyl alcohol derivative (E0, 903 mg, 3.36 mmol)3.5g of acidic alumina and 300mL of toluene, under argon protection, dark reaction 90 C for 35h, the solution was dark green.After cooling to room temperature, the reaction mixture was suction filtered, the filter cake was washed with dichloromethane, the filtrate and the washings were combined, the solvent was spin dried,The crude product was separated by column chromatography, and the resulting crude product was recrystallized from absolute ethanol to give 210 mg of a light yellow solid in a yield of 22%. Yield 55%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101597-25-5, 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Gantian Optical Materials Co., Ltd.; Gan Jiaan; (9 pag.)CN104016996; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 2867-59-6, 3-Aminobutan-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, 2867-59-6, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C4H11NO

6-(4-Chlorophenyl)-2-(3-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (70 mg, 0.20 mmol) was dissolved in anhydrous DMF (1.5 mL). (3RS)-3-Aminobutan-1 -ol (36.2 mg, 0.41 mmol), N-ethyl-N-isopropylpropan-2-amine (0.159 mL, 0.91 mmol), and propane phosphonic acid anhydride (T3P, 178 mu, 50% in DMF, 305mueta-iotaomicronIota) were successively added. It was stirred at rt overnight. The crude reaction mixture was purified by RP-HPLC (column: X-Bridge C18 5muetaiota 100x30mm, mobile phase: (water + 0.2 vol% aqueous ammonia (32%)) / acetonitrile, gradient) to yield 47 mg (56%) of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm] = 1 .19 (d, 3H), 1.59 – 1 .74 (m, 2H), 3.48 (t, 2H), 4.08 – 4.20 (m, 1 H), 4.50 (br s, 1 H), 7.34 – 7.42 (m, 1 H), 7.52 – 7.66 (m, 5H), 7.96 – 8.03 (m, 2H), 8.63 (s, 1 H), 9.31 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2867-59-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); SCHMEES, Norbert; GUTCHER, Ilona; IRLBACHER, Horst; BADER, Benjamin; ZHAO, Na; PLATTEN, Michael; (437 pag.)WO2017/202816; (2017); A1;,
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Electric Literature of 764-48-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 764-48-7, name is Ethylene Glycol Vinyl Ether. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.

According to the analysis of related databases, 764-48-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Quinio, Pauline; Kohout, Laura; Roman, Daniela Sustac; Gaar, Jakob; Karaghiosoff, Konstantin; Knochel, Paul; Synlett; vol. 27; 11; (2016); p. 1715 – 1719;,
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Synthetic Route of 101597-25-5, 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.101597-25-5, name is 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, molecular formula is C17H16O3, molecular weight is 268.31, as common compound, the synthetic route is as follows.

2-Phenylthio-1,4-dihydroxynaphthalene (2 g) from Step 1 and 1,1-bis(4-methoxyphenyl)-2-propyn-1-ol (2.25 g) from Step 2 of Example 1 were added to a reaction flask containing 70 ml of toluene and stirred at room temperature. A catalytic amount of p-toluenesulfonic acid (about 100 mg) was added and stirred for 4 hours under a nitrogen atmosphere. Afterwards, the reaction mixture was poured into 50 ml of 10 weight percent aqueous sodium hydroxide solution. The organic layer was separated, washed and dried over anhydrous sodium sulfate. Evaporation of solvent resulted in an oily product which was purified using a silica gel column and a 1:1 mixture of chloroform:hexane as the eluant. The photochromic fractions were combined and the eluant was removed under vacuum. The resulting product was induced to crystallize from diethyl ether. The recovered product (2.5 g) had a melting point of 152-154C. A nuclear magnetic resonance (NMR) spectrum showed the product to have a structure consistent with 2,2-bis(4-methoxyphenyl)-5-phenylthio-6-hydroxy-2H-naphtho[1,2-b]pyran.

Statistics shows that 101597-25-5 is playing an increasingly important role. we look forward to future research findings about 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol.

Reference:
Patent; TRANSITIONS OPTICAL, INC.; EP994871; (2006); B1;,
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Reference of 24006-92-6, Adding some certain compound to certain chemical reactions, such as: 24006-92-6, name is (4,5-Dichloro-1,2-phenylene)dimethanol,molecular formula is C8H8Cl2O2, 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 24006-92-6.

Into a 100-mL round-bottom flask, was placed a solution of (4,5-dichloro-1,2-phenylene)dimethanol (500 mg, 2.41 mmol, 1.00 equiv) in dichloromethane (50 mL) and tribromophosphane (1.30 g, 4.80 mmol, 2.00 equiv). The resulting solution was stirred overnight at room temperature. The mixture was poured into 50 mL of water/ice. The resulting solution was extracted with 3×100 mL of ethyl acetate, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). The collected fraction was concentrated under vacuum to give 1,2-bis(bromomethyl)-4,5-dichlorobenzene (400 mg, 50%) as off-white oil. 1H-NMR (CDCl3, 4001411z, ppm): delta 7.48 (s, 2H), 4.57 (s, 4H).

According to the analysis of related databases, 24006-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Forma Therapeutics, Inc.; Bair, Kenneth W; Barczak, Nicholas; Han, Bingsong; Lancia, JR., David R.; Liu, Cuixian; Martin, Matthew W; Ng, Pui Yee; Rudnitskaya, Aleksandra; Thomason, Jennifer R; Zablocki, Mary Margaret; Zheng, Xiaozhang; (195 pag.)US2016/264518; (2016); A1;,
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