Tag: M.W=100-200

Electric Literature of 205877-13-0, 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.205877-13-0, name is (2-Amino-3-methoxyphenyl)methanol, molecular formula is C8H11NO2, molecular weight is 153.1784, as common compound, the synthetic route is as follows.

General procedure: To a solution of 1a (1.2 g, 7.61 mmol) in CH2Cl2 (20 mL) was added MnO2 (2.6 g, 30.1 mmol) and stirred at rt under an Ar atmosphere. After 23 h with stirring, the reaction mixture was filtrated and evaporated. The residue was crystallized from AcOEt to give 7a (1.0 g, 85%) as a yellow needle crystal.

The chemical industry reduces the impact on the environment during synthesis 205877-13-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Ida, Yoshihiro; Matsubara, Ayaka; Nemoto, Toru; Saito, Manabu; Hirayama, Shigeto; Fujii, Hideaki; Nagase, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 20; 19; (2012); p. 5810 – 5831;,
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Adding a certain compound to certain chemical reactions, such as: 38584-37-1, 3-(Hydroxymethyl)adamantan-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, Application In Synthesis of 3-(Hydroxymethyl)adamantan-1-ol, blongs to alcohols-buliding-blocks compound. Application In Synthesis of 3-(Hydroxymethyl)adamantan-1-ol

(2) 5.0 Parts of the salt represented by the formula (g), 2.1 parts of (3-hydroxy-1-adamantyl)methanol, 50 parts of toluene and 0.3 part of concentrated sulfuric acid were mixed. The mixture obtained was heated and refluxed for 22 hours. The mixture was cooled, and then, concentrated. To the residue obtained, 90 parts of chloroform was added, and the solution obtained was repeated to wash with an ion-exchanged water until the aqueous layer obtained was neutralized. The organic layer obtained was concentrated and the residue obtained was mixed with 49 parts of ethyl acetate. The resultant mixture was stirred and filtrated to obtain the solid. The solid obtained was dried to obtain 5.4 parts of the salt represented by the above-mentioned formula (b). The 1H-NMR spectrum of the salt obtained was the same as that of the salt obtained in above-mentioned Salt Synthesis Example 1.

The synthetic route of 38584-37-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; US2008/86014; (2008); A1;,
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Electric Literature of 81156-68-5, 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 81156-68-5, name is 2,4-Dichlorophenethyl alcohol. This compound has unique chemical properties. The synthetic route is as follows.

(ii) 3-[2-(2,4-Dichlorophenyl)-Ethoxy]-4-Ethoxy-Benzoic Acid Ethyl Ester 0.5 g (2.38 mmol) of 4-Ethoxy-3-hydroxy-benzoic acid ethyl ester was dissolved in 10 ml of anhydrous tetrahydrofuran. To this solution was added 0.5 g (2.62 mmol) of 2-(2,4-Dichlorophenyl)-ethanol, 2.38 g (equivalent to 7.13 mmol PPh3) of triphenylphosphine derivatized polystyrene and 1.24 g (7.13 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluding with ethyl acetate/n-heptane (1/4).

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 81156-68-5, 2,4-Dichlorophenethyl alcohol.

Reference:
Patent; Nazare, Marc; Will, David William; Peyman, Anuschirwan; Matter, Hans; Zoller, Gerhard; Gerlach, Uwe; US2002/198195; (2002); A1;,
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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.6214-45-5, name is (4-Butoxyphenyl)methanol, molecular formula is C11H16O2, molecular weight is 180.24, as common compound, the synthetic route is as follows.HPLC of Formula: C11H16O2

(4-butoxyphenyl)methanol (0.48 mmol, 91.3 mg) was dissolved in tetrahydrofuran (2.0 ml) and NaH (0.96 mmol, 60 %, 38.4 mg) was added in one portion. After gas evolution ceased the suspension was added to a solution of 4-nitrophenyl N-[(2,4- difluorophenyl)methyl]-N-(l-methylpiperidin-4-yl)carbamate (130 mg, 0.32 mmol) dissolved in tetrahydrofuran (2.0 ml). The mixture was stirred for 4 hours, the mixture was partitioned between diethyl ether and 0.2 M NaOH, the organic phase was collected, dried, and the crude was purified by column chromatography using silicon dioxide gel, eluting with 10-25 % methanol in ethyl acetate to afford the title compound (86 mg, yield 60 %): NMR (400 MHz, Chloroform-^) delta 7.42 – 6.97 (m, 3H), 6.97 – 6.63 (m, 4H), 5.25 – 4.96 (m, 2H), 4.58 – 4.33 (m, 2H), 4.23 – 3.72 (m, 1H), 3.96 (t, 2H), 2.85 (d, 2H), 2.25 (s, 3H), 2.13 – 1.86 (m, 2H), 1.84 – 1.41 (m, 8H), 0.98 (t, 3H); LC-MS : 447.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6214-45-5, (4-Butoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; WAHLSTROeM, Larisa, Yudina; BORGSTROeM, Bjoern, Gustav; VON WACHENFELDT, Henrik; BERGNER, Magnus Gustav, Wilhelm; (146 pag.)WO2019/40104; (2019); A2;,
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Application of 2987-05-5, 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 2987-05-5, name is 4-(Methylamino)cyclohexanol. This compound has unique chemical properties. The synthetic route is as follows.

Example 1 N-(4-bromo-2-fluorophenyl)-N’-(4-hydroxycyclohexyl)-N,N’-dimethylureaStep 1. 4-(methylamino)cyclohexanol hydrochloride; To a suspension of lithium tetrahydroaluminate (2.70 g, 0.0711 mol) in tetrahydrofuran (120.0 mL, 1.479 mol) was added tert-butyl (4-hydroxycyclohexyl)carbamate (3.00 g, 0.0139 mol). The reaction mixture was heated at reflux overnight. After cooling to rt, the mixture was carefully quenched with successively dropwise additions of water (2.70 mL, 0.150 mol), 3.750 M of sodium hydroxide in water (2.70 mL) (15%), and water (8.100 mL, 0.4496 mol). After stirring at rt for Ih, the mixture was filtered through a pad of Celite. The filtrate was dried with magnesium sulfate and evaporated to dryness. The crude material was used directly in next step. LCMS (M+H) 130.2. The crude amine was treated with 40 mL of 4 M HCl in dioxane solution at rt for 4 h, then evaporated to dryness to afford the corresponding HCl salt (2.16 g, 93.57%).

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 2987-05-5, 4-(Methylamino)cyclohexanol.

Reference:
Patent; INCYTE CORPORATION; WO2007/130898; (2007); A1;,
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Electric Literature of 3685-27-6, 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 3685-27-6, name is trans-4-(Hydroxymethyl)cyclohexanol. This compound has unique chemical properties. The synthetic route is as follows.

176b) (1 r,4r)-4-((3-Bromophenoxy)methyl)cyclohexanol A solution of 3-bromophenol (2 g, 1 1 .56 mmol), triphenylphosphine (3.03 g, 1 1 .56 mmol) and (1 r,4r)-4-(hydroxymethyl)cyclohexanol (2.5 g, 19.20 mmol) in tetrahydrofuran (THF) (150 mL) was added DIAD (2.70 mL, 1 3.87 mmol) in tetrahydrofuran (THF) (150 mL) slowly under nitrogen at 25 C. The reaction mixture was stirred at 25 C for 16 h. The reaction mixture was concentrated. The crude product was purified on silica gel chromatography (hexane:ethyl acetate = 4:1 ) to provide the title compound (1 r,4r)-4-((3- bromophenoxy)methyl)cyclohexanol (1 .2 g, 2.1 04 mmol, 18.20 % yield) as an oil. 1 H NMR (500 MHz, DMSO) delta 7.22 (t, J = 8.1 Hz, 1 H), 7.14 – 7.06 (m, 2H), 6.98 – 6.88 (m, 1 H), 4.52 (d, J = 4.4 Hz, 1 H), 3.90 – 3.73 (m, 2H), 1 .91 – 1 .75 (m, 4H), 1 .06 (dd, J = 1 8.7, 8.5 Hz, 2H), 0.84 (ddd , J = 1 3.0, 7.7, 4.6 Hz, 2H).

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 3685-27-6, trans-4-(Hydroxymethyl)cyclohexanol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); 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. 17366-48-2, name is exo-8-Azabicyclo[3.2.1]octan-3-ol hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 17366-48-2

To a stirred solution of exo-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (2.049 g, 12.52 mmol) and DIPEA (5.96 ml, 34.1 mmol) in DMF (15 ml) was added 5-bromo-2-chlorobenzenesulfonyl chloride (3.30 g, 11.38 mmol) at 0 C., the mixture was slowly rose to rt in 2 h and stirred at rt for 1 h. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The residue was used directly for next step. ESI-MS (M+H): 380.0, 382.0. To a mixture of the compound from Step 23a (4.3 g, 11.30 mmol) and imidazole (1.922 g, 28.2 mmol) in DMF (15 ml) was added TBSCl (2.043 g, 13.55 mmol) at 0 C. The resulting mixture was stirred overnight at rt. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (3.92 g, 70% over 2 steps). ESI-MS (M+H): 494.1, 496.1.H NMR (400 MHz, CDCl3) delta 8.21 (d, J=2.4 Hz, 1H), 7.55 (dd, J=8.4, 2.4 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 4.27 (dd, J=4.7, 2.8 Hz, 2H), 3.95 (td, J=10.6, 5.4 Hz, 1H), 1.97 (dd, J=8.3, 4.3 Hz, 2H), 1.83 (ddd, J=13.2, 5.9, 3.1 Hz, 2H), 1.77-1.60 (m, 4H), 0.83 (s, 9H), 0.00 (s, 6H). To a stirred solution of the compound from Step 23b (1.00 g, 2.02 mmol) in THF (30.0 ml) was added a solution of 2.5 M n-BuLi (0.889 ml, 2.22 mmol) in hexanes at -78 C. and DMF (0.469 ml, 6.06 mmol). The resulting mixture was stirred at -78 C. for 30 minutes. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (250 mg, 28%). ESI-MS (M+H): 444.2, 446.2. To a stirred solution of the compound from Step 23c (340 mg, 0.766 mmol) in DMF (8.0 ml) was added trimethyl(trifluoromethyl)silane (654 mg, 4.60 mmol) at 0 C. The resulting mixture was warmed up slowly to rt and kept for 30 minutes. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was taken into next step without further purification. ESI-MS (M+H): 586.1, 588.1.To a stirred solution of the compound from Step 23d (90 mg, 0.154 mmol) in MeOH (4.0 ml) was added K2CO3 (212 mg, 1.535 mmol) at 0 C. The resulting mixture was stirred at 0 C. for 1 h. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (62 mg, 79%). ESI-MS (M+H): 514.2, 516.2.To a stirred solution of the compound from Step 23e (50 mg, 0.097 mmol) in DCM (2 ml) was added Dess-Martin periodinane (61.9 mg, 0.146 mmol) at 0 C. . The resulting mixture was stirred at 0 C. for 1 h. The solution was partitioned between EtOAc and Na2S2O3 aqueous solution. The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (40 mg, 80%). ESI-MS (M+H): 512.2, 514.2.To a stirred solution of the compound from Step 23f (15 mg, 0.029 mmol) and 3,4,5-trifluoroaniline (10.77 mg, 0.073 mmol) in toluene (1 mL) was added titanium(IV) isopropoxide (0.051 ml, 0.176 mmol). The resulting mixture was stirred at reflux (120 C.) for 15 h. The mixture was cooled to rt. Then sodium triacetoxyborohydride (18.63 mg, 0.088 mmol) was added. The mixture was stirred at rt for 1 h. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (5 mg, 27%). ESI-MS (M+H): 643.2, 645.2.To a stirred solution of the compound from Step 23g (6 mg, 9.3 mumol) in MeOH (1.0 ml) was added a solution of 4N HCl (0.12 ml, 0.47 mmol) at 0 C. The resulting mixture was stirred at 0 C. for 45 minutes. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, MeOH/DCM) to give the title compound as a white solid (4 mg, 81%). ESI-MS (M+H): =529.1, 531.1.1H NMR (400 MHz, MeOH-d4) delta 8.30 (d, J=2.2 Hz, 1H), 7.78 (dd, J=8.3, 2.2 Hz, 1H), 7.68 (d, J=8.2 Hz, 1H), 6.62-6.39 (m, 2H), 5.50 (q, J=7.5 Hz, 1H), 4.33-4.16 (m, 2H), 3.98 (dt, J=10.8, 5.1 Hz, 1H), 2.02-1.86 (m, 2H), 1.84-1.55 (m, 6H).

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, 17366-48-2, exo-8-Azabicyclo[3.2.1]octan-3-ol hydrochloride.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Or, Yat Sun; Jin, Meizhong; Kass, Jorden; Cao, Hui; Gao, Xuri; Li, Wei; Peng, Xiaowen; Qiu, Yao-Ling; (43 pag.)US2017/217974; (2017); A1;,
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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.81156-68-5, name is 2,4-Dichlorophenethyl alcohol, molecular formula is C8H8Cl2O, molecular weight is 191.06, as common compound, the synthetic route is as follows.Recommanded Product: 2,4-Dichlorophenethyl alcohol

Example 5 Preparation of methyl 2- [4- (2-F2. 4-DICHLOROPHENYL) ETHOXY) PHENYL- THIO]ISOBUTYRATE (ST2531) The title product was prepared according to the procedure described in Method B starting from methyl 2- (4- hydroxyphenylthio) iso-butyrate (prepared as described in example 3) (0.280 g, 1.24 mmol) and DIAD (0. 325 g, 1.61 mmol) dissolved in 3 mL of anhydrous THF and added dropwise to a solution of 2,4- dichlorophenetylalcohol (0.260 g, 1.36 mmol) and triphenylphosphine (0.422 g, 1.61 mmol) in 4 mL of anhydrous THF at 0C. The reaction was left overnight under magnetic stirring at room temperature After this period, the solvent was evaporated and the residue purified by silica gel chromatography using HEXANE/ACOET 9.6/0. 4 as eluent. 0.346 g of product were obtained (yield: 70%); Mp: 73-74C ; TLC: silica gel, eluent hexane/AcOEt 9/1, Fr: 0.26 ; 1H NMR (CDCIs, 300 MHz) B : 7.35 (m, 3H), 7.22 (m, 2H), 6.83 (d, 2H), 4.18 (t, 2H), 3.65 (s, 3H), 3.20 (t, 2H), 1.45 (s, 6H); HPLC: Column: Inertisil ODS-3 (5, UM) 4.6 x 250 mm, T: room temperature, mobile phase CH3CN/H20 85/15 (v/v), pH: as is, flow rate: 1 mL/min, 205 nm UV detector, retention time 12.58 min; KF: 0.4 % H20 ; E. A. conforming for CL9H20CL203S.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,81156-68-5, 2,4-Dichlorophenethyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.p.A.; WO2004/56355; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 155310-11-5, 3-Amino-2,2-difluoropropan-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, SDS of cas: 155310-11-5, blongs to alcohols-buliding-blocks compound. SDS of cas: 155310-11-5

Into a 40-mL round-bottom flask, was placed 3-amino-2, 2-difluoropropan-l-ol (1 g, 9.002 mmol, 1 equiv), DCM (10 mL), Et3N (1.37 g, 13.539 mmol, 1.50 equiv), TsCl (1.72 g, 9.002 mmol, 1.0 equiv). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0: 1- 1:2). This resulted in 600 mg (25.13%) of N-(2,2-difluoro- 3-hydroxypropyl)-4-methylbenzene-l-sulfonamide as a white solid. 1H-NMR- 1(300 MHz, CDCl3, ppm) d 7.76- 7.73 (d, J = 9.0 Hz, 2H), 7.35 – 7.32 (d, J = 9.0 Hz, 2H), 5.04- 5.00 (m, 1H), 3.91 – 3.83 (m, 2H), 3.46 – 3.35 (m, 2H), 2.45 (s, 3H).

The synthetic route of 155310-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); 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. 38594-42-2, name is (2,3-Dichlorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6Cl2O

A solution of 21.54 g of the compound obtained in the preceding step and 18.6 ml of triethylamine in 150 ml of DCM is cooled in an ice bath, a solution of 10.4 ml of methanesulphonyl chloride in 50 ml of DCM is added dropwise at a temperature of less than 10 C. and the mixture is kept stirred while allowing the temperature to return to RT. It is concentrated under vacuum, the residue is extracted with ether, and the medium is washed twice with a buffer solution pH=2, with a saturated solution of NaCl, dried over Na2SO4 and the solvent is evaporated under vacuum. 29.25 g of the expected product are obtained.

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, 38594-42-2, (2,3-Dichlorophenyl)methanol.

Reference:
Patent; Emonds-Alt, Xavier; Proietto, Vincenzo; US2004/180890; (2004); A1;,
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