Month: August 2021

Electric Literature of 27489-62-9, 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. 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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.

A mixture of [6-chloro-4-(tetrahydro-pyran-4-sulfonyl)-pyridin-2-yl]-(5-phenyl-2H- pyrazol-3-yl)-amine formate salt (0.1 g, 0.22 mmol), irans-4-aminocyclohexanol (0.19 g, 1.61 mmol) and DIPEA (0.27 mL, 1.61 mmol) in anhydrous DMSO (1.0 mL) was flushed with nitrogen and heated to 120 C in a sealed tube. Further additions of trans- – aminocyclohexanol (0.19 g, 1.61 mmol) were carried out approximately every 2 – 3h while monitoring by LC-MS until the amount of product did not increase further (no heating or addition of irans-4-aminocyclohexanol overnight). The total heating time was 24h and the total amount of irans-4-aminocyclohexanol added 58.5 equivalents. The reaction mixture was then allowed to cool down to room temperature and partitioned between EtOAc (10 mL) and saturated aq. ammonium chloride solution (5 mL). The phases were separated and the aqueous phase extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried (MgS04), filtered and evaporated in vacuo. The crude material was purified by flash chromatography eluting with MeOH (0 – 10 %) in DCM to give the title compound as a light brown solid (0.07 g, 68 %). XH NMR (500 MHz, DMSO- d6): delta 12.66 (br. s., 1 H), 9.40 (br. s., 1 H), 7.75 – 7.66 (m, 2 H), 7.51 – 7.41(m, 2 H), 7.38 – 7.29 (m, 1 H), 6.93 – 6.74 (m, 2 H), 6.63 (br. s., 1 H), 6.15 (br. s., 1 H), 4.58 (br. s., 1 H), 3.91 (dd, .7=11.2, 3.8 Hz, 2 H), 3.76 (br. s., 1 H), 3.44 (br. s., 2 H), 2.09 – 1.94 (m, 2 H), 1.92 – 1.82 (m, 2H), 1.81 – 1.71 (m, 2 H), 1.66 – 1.48 (m, 2 H), 1.38 – l .l l(m, 4 H). MS: m/z = 498.1 (M+H)+.

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 27489-62-9, trans-4-Aminocyclohexanol.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20605-01-0, Diethyl 2,2-bis(hydroxymethyl)malonate, 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, 20605-01-0, blongs to alcohols-buliding-blocks compound. Computed Properties of C9H16O6

Diethyl 2,2-bis(hydroxymethyl)malonate (28.3 mmol; 6.23 g) was coevaporated twice from dry pyridine and dissolved in the same solvent (20 mL). tert-Butyldimethylsilyl chloride (25.5 mmol; 3.85 g) in dry pyridine (10 mL) was added portionwise. The reaction was allowed to proceed for 4 days. The mixture was evaporated to a solid foam, which was then equilibrated between water (200 mL) and DCM (4×100 mL). The organic phase was dried on Na2SO4. The product was purified by silica gel chromatography eluting with 10% ethyl acetate in DCM. The yield was 78%. 1H NMR (CDCl3) delta 4.18-4.25 (m, 4H, OCH2Me), 4.10 (s, 2H, CH2OSi), 4.06 (s, 2H, CH2OH), 2.63 (br s, 1H, OH), 1.26 (t, J=7.0 Hz, 6H, OCH2CH3), 0.85 (s, 9H, Si-SMe3), 0.05 (s, 6H, Me-Si). 13C NMR (CDCl3) delta 169.2 (CO), 63.3 (CH2OH), 62.8 (CH2OSi), 61.6 (spiro C), 61.4 (OCH2Me), 25.6 [C(CH3)3], 18.0 (Si-CMe3), 14.0 (OCH2CH3), -3.6 (Si-CH3). MS [M+H]+ obsd. 335.7, calcd. 335.2; [M+Na] obsd. 357.6, calcd. 357.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20605-01-0, its application will become more common.

Reference:
Patent; Alios BioPharma, Inc.; US2010/240604; (2010); A1;,
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Related Products of 1124-63-6, 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. 1124-63-6, name is 3-Cyclohexylpropan-1-ol. A new synthetic method of this compound is introduced below.

To a stirred solution of 4-nitrophenol (4) (1.30 g, 8.35 mmol) and PPh3 (3.20 g, 12.2 mmol) in THF (30.0 mL) were added diisopropyl azodicarboxylate (2.40 mL, 12.2 mmol) and 3-cyclohexyl-1-propanol (1.91 mL, 12.2 mmol) at 0 C. After stirring for 2 h at ambient temperature, the reaction mixture was quenched with H2O and then extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (EtOAc : n-hexane = 1 : 24 to 1 : 15) to afford 2.23 g (91%) of 18 as a colorless oil: 1H NMR (CDCl3, 400 MHz) delta 8.15 (d, 2H, J= 7.0 Hz), 6.91 (d, 2H, J = 7.0 Hz), 3.99 (t, 2H, J = 6.6 Hz), 1.80 (quintet, 2H, J = 7.2 Hz), 1.67 (m, 5H), 1.31 (m, 2H), 1.18 (m, 4H), 0.89 (m, 2H); 13C NMR (CDCl3, 100 MHz) delta 164.3, 141.3, 125.9, 114.4, 69.3, 37.4, 33.6, 33.3, 26.7, 26.4, 26.4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1124-63-6, 3-Cyclohexylpropan-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Jo, Jeyun; Kim, Heegyu; Oh, Ji Youn; Kim, Soyeong; Park, Yeong Hye; Choi, Hyeonjin; Jeong, Jee-Yeong; Jung, Young-Suk; Yun, Hwayoung; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
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Reference of 627-30-5, Adding some certain compound to certain chemical reactions, such as: 627-30-5, name is 3-Chloropropan-1-ol,molecular formula is C3H7ClO, 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 627-30-5.

MTCOH (8.82 g, 55 mmol) was converted to MTCOCl using standard procedures with oxalyl chloride. In a dry 250 mL round bottom flask equipped with a stir bar, the formed intermediate was dissolved in 150 mL of dry methylene chloride. Under nitrogen flow an addition funnel was attached in which 3-chloropropanol (4.94 g, 4.36 mL, 52.25 mmol), pyridine (3.95 g, 4.04 mL, 55 mmol), and 50 mL of dry methylene chloride was charged. The flask was cooled to 0 C. using an ice bath and the top solution was added drop wise during a period of 30 minutes. The formed solution was stirred for an additional 30 minutes before the ice bath was removed and the solution was stirred for an additional 16 hours under nitrogen. The crude product MTC-PrCl was directly applied onto a silica gel column and the product was separated by eluting with 100% methylene chloride. The product fractions were removed and the solvent was evaporated, yielding the product as off-white oil, which crystallized upon standing. Yield 11 g (85%). 1H-NMR (CDCl3) delta: 4.63 (d, 2H, CH2), 4.32 (t, 2H, CH2), 4.16 (d, 2H, CH2), 3.55 (t, 2H, CH2), 2.09 (m, 2H, CH2), 1.25 (s, 3H, CH3).

According to the analysis of related databases, 627-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERNATIONAL BUSINESS MACHINES CORPORATION; Hedrick, James L.; Lee, Ashlynn L. Z.; Ng, Victor W. L.; Yang, Yi Yan; US2014/301970; (2014); A1;,
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Electric Literature 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.

Step A: Preparation of 2-[1-(4-Amino-phenyl)-2,2,2-trifluoro-1-trifluoromethyl-ethoxymethyl]-pyrrolidine-1-carboxylic Acid tert-butyl Ester To a mixture of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.30 g), 2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g), PPh3 (1.56 g) and molecular sieves 4 A in THF (100 mL) was added DEAD (0.93 mL) slowly.The reaction was stirred at RT for 5 h and at reflux for overnight. After filtration to remove solids, the filtrate was concentrated and the residue was taken into ether.The organic phase was washed with saturated NaHCO3 and brine.The organic layer was dried over MgSO4 and evaporated to give a crude product as a very viscous brown oil which was chromatographed through silica gel (400 g, 2:1:7 to 3:1:6 EtOAc/Et3N/hexanes) to afford 2-[1-(4-amino-phenyl)-2,2,2-trifluoro-1-trifluoromethyl-ethoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown oil. The title compound was synthesised from the above aniline in analogous to what was described previously. MS: (ES+) 654 (M+H). Calc’d. for C31H33F6N5O4-653.62.

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; Amgen Inc.; US2003/225106; (2003); A1;,
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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 403-41-8, name is 1-(4-Fluorophenyl)ethyl Alcohol. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 1-(4-Fluorophenyl)ethyl Alcohol

To a stirred solution l-(4-fluorophenyl)ethan-l-ol (2, 0.5 g, 3.57 mmol) in DCM (5 mL), was added SOCl2(0.7 mL, 7.10 mmol) drop wise at 0 C and the reaction mixture was stirred at rt for 1 h (Reaction condition b). The reaction mixture was evaporated under vacuum and dried to afford the product as brown oil (3) (0.5 g, 89%, Yield).XHNMR (400 MHz, DMSO-d6) delta (ppm): 7.53-7.51 (m, 2H), 7.21-7.16 (m, 2H), 5.36-5.33 (m, 1H), 1.76 (d, = 6.8 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 403-41-8.

Reference:
Patent; JUBILANT BIOSYS LIMITED; HALLUR, Gurulingappa; DURAISWAMY, Athisayamani Jeyaraj; PURRA, Buchi Reddy; RAO, N.V.S.K.; RAJAGOPAL, Sridharan; KRISTAM, Rajendra; (200 pag.)WO2019/77631; (2019); A1;,
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Related Products of 124-68-5 ,Some common heterocyclic compound, 124-68-5, molecular formula is C4H11NO, 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.

A (2-Hydroxy-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester 2-Amino-2-methyl-propan-1-ol (53 g, 0.59 mol) and di-tert-butyl dicarbonate (65.0 g, 0.297 mol) were combined in H2O (500 mL) and stirred at 25 C. for 1 h. The reaction mixture was extracted with CHCl3 (2*250 mL) The organics were dried and concentrated to a white amorphous solid which was recrystallized from hot hexanes to afford desired material (30 g, 53%) as a white solid: 13C NMR (CD3OD, 100 MHz) delta 157.76, 80.135, 70.095, 54.992, 29.247, 24.695.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 124-68-5, 2-Amino-2-methyl-1-propanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lombardo, Louis J.; Bhide, Rajeev S.; Kim, Kyoung S.; Lu, Songfeng; US2003/232832; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 67853-03-6, Methyl 3-(hydroxymethyl)benzoate, 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, 67853-03-6, blongs to alcohols-buliding-blocks compound. Product Details of 67853-03-6

To the solution of compound B4 (28 g, 0.168 mol) in 700 mL of Et2O was added PBr3 (17.4 mL, 0.185 mol) dropwise. The solution was stirred for 2 h, and then the reaction was poured into 500 mL of ice-water. The aqueous layer was extracted with Et2O. The combined organic layers were washed with sat. NaHCO3, water, and brine consecutively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure to give 34 g of compound B5 as an oil (yield: 70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67853-03-6, its application will become more common.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; KREMOSER, Claus; ABEL, Ulrich; STEENECK, Christoph; KINZEL, Olaf; WO2011/20615; (2011); A1;,
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Synthetic Route of 2240-88-2, 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. 2240-88-2, name is 3,3,3-Trifluoropropan-1-ol. A new synthetic method of this compound is introduced below.

To the solution of 2.00 g Preparation 9a3 (8.61 mmol) in acetonitrile 2.38 g K2C03 (17.2 mmol), then 3,3,3-trifluoropropan-1-ol were added and the so obtained mixture was stirred for I Oh at 60°C. The reaction mixture was cooled, filtered and the filtrate concentratedunder reduced pressure. The residue was purified via flash chromatography using heptane and ethyl-acetate as eluents to give 4-(dimethoxymethyl)-2-(3,3,3-trifluoropropoxy) pyrimidine.?11 NMR (400 MHz, DMSO-d6): 8.68 (d, 111), 7.22 (d, 111), 5.22 (s, 111), 4.53 (t, 211), 3.33 (s, 611), 2.83 (m, 211).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2240-88-2, 3,3,3-Trifluoropropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; SZLAVIK, Zoltan; CSEKEI, Marton; PACZAL, Attila; SZABO, Zoltan; SIPOS, Szabolcs; RADICS, Gabor; PROSZENYAK, Agnes; BALINT, Balazs; BRUNO, Alain; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; PERRON-SIERRA, Francoise; WO2015/97123; (2015); A1;,
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Reference of 873-76-7, 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. 873-76-7, name is (4-Chlorophenyl)methanol, molecular formula is C7H7ClO, 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 a suspension of polymer-bound triphenylphosphine (1.2 mmol) in anhydrous acetonitrile (10 mL) were added iodine (1 mmol) and 1,6-hexanediol diol (1mmol). The reaction mixture was irradiated in microwave reactor at 120 C for 3 min. The reaction mixture was filtered over a filter paper and washed with chloroform.The filtrate was extracted with aqueous sodium thiosulfate solution and dried with anhydrous sodium sulfate.The reafter, solvent was removed under reduced pressure to obtain 6-iodohexan-1-ol (30) in 93%

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 873-76-7, (4-Chlorophenyl)methanol.

Reference:
Article; Das, Diparjun; Chanda, Tridib; Rokhum, Lalthazuala; Acta Chimica Slovenica; vol. 62; 4; (2015); p. 775 – 783;,
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