Tag: M.W=100-200

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. 187731-65-3, name is (2-Amino-4-methoxyphenyl)methanol. A new synthetic method of this compound is introduced below., Quality Control of (2-Amino-4-methoxyphenyl)methanol

Synthesis of 2-amino-4-methoxybenzaldehyde. A mixture of (2-amino-4-methoxyphenyl)methanol (20 g, 131.0 mmol) and manganese oxide (68 g, 786.0 mmol) in dichioromethane (300 mL) was stuffed at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated. The residuewas purified by silica gel chromatography (petroleum ether:ethyl acetate = 6:1) to give the title compound (7 g, 35%) as a yellow solid. MS (ES+) C8H9N02 requires: 151, found: 152 [M + H].

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Reference:
Patent; BLUEPRINT MEDICINES; BIFULCO, Neil, Jr.; BROOIJMANS, Natasja; HODOUS, Brian, L.; KIM, Joseph, L.; MIDUTURU, Chandrasekhar, V.; WO2014/11900; (2014); A2;,
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Reference of 16308-92-2, 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 16308-92-2, name is (2,4-Dimethylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a suspension of benzyl alcohol (1.1 g, 0.0101 mol), aniline (0.94 g, 0.0101 mol), and ethyl vinyl ether (0.728 g, 0.0101 mol) in a mixture of EtOAc:DMSO (6.0: 2.0 mL) was added T3P (2.0 mmol, 50% solution in ethyl acetate) at 0oC, and the resulting mixture was stirred at room temperature for 45 h. Progress of the reaction was monitored by TLC. The reaction mass was concentrated, the obtained residue was neutralized with 10% NaHCO3 solution, and then extracted with ethyl acetate (2 x 20 mL), the combined organic phase was washed with water and brine solution, and dried over anhydrous sodium sulphate. The organic phase was evaporated and the crude product was purified by column chromatography using silica gel mesh 100-200 (15% EtOAc in hexanes).

According to the analysis of related databases, 16308-92-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Narasimhamurthy, Kereyagalahally H.; Chandrappa, Siddappa; Kumar, Kothanahally S. Sharath; Swaroop, Toreshettahally R.; Rangappa, Kanchugarakoppal S.; Chemistry Letters; vol. 42; 9; (2013); p. 1073 – 1075;,
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Application of 1777-82-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1777-82-8 as follows.

The reactants used were 2,4-dichlorobenzyl alcohol (i.e., R1 in the formula (I) was ortho, with two Cl) 1.0 mmol(177.0 mg), the experimental method and procedure were the same as in Example 1, ammonia water (1.8 mol / L) 5.0 mL, and the amount of catalyst cuprous bromide was5 mol% (7.2 mg), TEMPO was used in an amount of 5 mol% (7.8 mg), the reaction temperature was 80 C, the reaction time was 24 h, and the crude productPurification by column chromatography (petroleum ether: ethyl acetate = 10: 1) gave the pure title product, yielded 166.8 mg yield 97%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1777-82-8, its application will become more common.

Reference:
Patent; Zhejiang University of Technology; Zhang Guofu; Zhao Yiyong; Zhang Guihua; Ding Chengrong; Yu Yidong; Lv Jinghui; (10 pag.)CN106866326; (2017); A;,
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Synthetic Route of 1562-00-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1562-00-1 as follows.

Example A; 31 g of (E)-10-pentafluorosulfanyldec-9-enecarbonyl chloride, prepared as in Example 1, are dissolved in 100 g of THF, 2-hydroxyethanesulfonic acid Na salt (15 g) and triethylamine (10 g) are added, and the mixture is stirred at 30 C. for 6 hrs.In order to isolate the product, the mixture is added to ice/methyl tert-butyl ether, the water phase is extracted with this solvent, and all org. phases are evaporated. Ethanol and then 1.2 equivalents of sodium hydroxide are added. The mixture is warmed briefly, and, after cooling, the crystals formed are isolated and dried.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1562-00-1, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; US2009/264525; (2009); 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 4740-78-7, name is 1,3-Dioxan-5-ol. This compound has unique chemical properties. The synthetic route is as follows. category: alcohols-buliding-blocks

[00768] To a solution of compound 263-1 (2 g, 6.55 mmol, 1 eq) in THF (2 mL) were added compound 263-la (1.02 g, 9.83 mmol, 1.5 eq) and PPh3 (2.58 g, 9.83 mmol, 1.5 eq). The mixture was degassed with N2 for 3 times. Then DIAD (1.99 g, 9.83 mmol, 1.9 mL, 1.5 eq) was added to the mixture dropwised at 0C. The mixture was stirred at 20C for 16 hr. LCMS showed that the starting material was remained and 33% of desired product was detected. TLC (PE/EA = 3/1, UV) showed that several spots were formed. The reaction mixture was concentrated in vacuum and the residue was diluted with EA (20 mL), washed with water (5 mL) and brine (5 mL). The organic phase was dried over Na2S04, filtered and concentrated in vacuum. The crude product was purified by column chromatography (Si02). Compound 263 (1.3 g, 2.79 mmol, 42.6% yield) was obtained. LCMS (ESI): RT = 0.885 min, mass calcd. For Ci8Hi6F3N502,391.13 m/z found 392.0 [M+H] +; 1HNMR (400 MHz, CDC13) 9.02 (s, 1H), 8.20 (dd, J= 7.92, 1.38 Hz, 1H), 7.51- 7.58 (m, 3H), 7.35- 7.42 (m, 1H), 7.30 (d, J= 8.54 Hz, 2H), 7.03- 7.08 (m, 1H), 5.12 (s, 1H), 4.85- 4.94 (m, 2H), 4.65- 4.80 (m, 2H), 4.00 – 4.07 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 4740-78-7.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
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Electric Literature of 56456-49-6, 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. 56456-49-6, name is 4-Chloro-2-fluorobenzyl alcohol, molecular formula is C7H6ClFO, 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.

(2) Then, 16.5 g of 4-chloro-2-fluorobenzylalcohol was dissolved in 150 ml of tetrahydrofuran and 1 ml of pyridine, to which 10 ml of thionyl chloride was added dropwise at 5 C., and the mixture was stirred for 2.5/6 hours. After cormpletion of the reaction, the reaction mixture was concentrated, and the precipitated crystals were collected by filtration. The filtrate was subjected to silica gel column chromatography, which afforded 18.5 g of 4-chloro-2-fluorobenzyl chloride. 1 H–NMR (250 MHz, CDCl3): delta (ppm) 4.59 (2 H, s), 7.09-7.17 (2 H, m), 7.36 (1 H, dd, J=7.9, 7.9 Hz)

According to the analysis of related databases, 56456-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Ltd.; US6100257; (2000); A;,
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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. 1450754-41-2, name is 2-(3-But-3-ynyl-3H-diazirin-3-yl)-ethanol. A new synthetic method of this compound is introduced below., Computed Properties of C7H10N2O

To a solution of ethan1-ol (200 mg,145 mrnoi, 1 equiv) in tetrahydrofuran (10 mL) at 24 C, was added carbonyidiimidazole(950 mg, 580 mmol, 4.00 equiv). The mixture was allowed to stir for 12 hours at 24 eQ Theproduct mixture was concentrated in vacuo to a solid residue. The residue was directly loadedto a hexaneequilibrated silica gel column and the desired material was eluted using a 50–100% ethyl acetate-hexane solvent, two steps). The irnidazole 5 was isolated as colorless oilafter concentration of the residual soR nt (320 mRf= 0.15 (40 ethyl acetate—he?ane; LV). f- NMR (500 MHz, ()Cl.). 8.13 (s, I]1 7.42-7..-1 I ,m, IH, H-. 7.03—7.u2 ,ni. I H 4.26—4 23 a. 2Ff, 7 1 :-iz, F).L99–i.96(m.3RHR:). I H–I S8(t,2H.i==Hz.H). I 6(– I 6{t,2H.i==7.I Hz.H). ?( >R (125 MHz. CDCI ). d I?4X.3 (C). I 7. I (CH. 130 7 Ci). 117. 1 ( H), 82 3(( , 6 (( H). o2 ) {OCH). 32 QH , 32.1) (( RI, 26.0 (CN , I . I ((?Ri) IR (AE R-FTIR) cm? 3291 (brj, 3 1 8 (w) 3 132 (rn,j, 2960 (w), 2921 (m,j, 2858 (m) 1 758 (s), 1588(s). 1525 mL 1473 (m). 1444 (m), 1404 (in), 1350 (w), 1316 (w). 1282 (? . 1240 (w), 1173(w), 1095 (m), 1058 (m) 1003 (v, 898 (m), 833 , 768 (w), 749 ( 6-l (v, 598 (w),526 (w). HRMSESI (m/z) [. L calculated for C H 1N4O2, 233. 1039. Ibund. 233.1064.

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Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; WOO, Christina, M.; GAO, Jinxu; (555 pag.)WO2018/226828; (2018); A2;,
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Related Products of 702-82-9, 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.702-82-9, name is 3-Aminoadamantan-1-ol, molecular formula is C10H17NO, molecular weight is 167.2481, as common compound, the synthetic route is as follows.

Example 8.2: (S)-l-[2-(3-Hydroxy-adamantan-l-ylamino)-acetyl]-pyrrolidine 2- carboxylic acid methyl ester (0115) In a clean and dry 1L four neck R.B.F. equipped with mechanical stirrer, thermometer pocket and a reflux water condenser under nitrogen charged dichloromethane (140 mL, 4V), 3-amino-adamantan-l -ol (35.58 g, 1.25 eq.), powdered potassium carbonate (70.51 g, 3.0 eq.) and potassium iodide (2.82 g, 0.1 eq.) under N2 and Stirred for 30 min. Meanwhile prepared a solution of (S)-l-(2-chloro-acetyl)-pyrrolidine-2-carboxylic acid methyl ester (35 g, l .O eq.) and dichloromethane (35 mL, IV) and added to the reaction mass in one lot. Heated the reaction mass to vigorous reflux and maintained for 6 h. Monitored progress of reaction by HPLC after 4 h. After complete conversion on HPLC, stopped heating and cooled reaction mass to 20-25C. Filtered the salt and washed the solid with DCM (70 mL, 2V). Charged the filtrate in 1 L RBF and cooled reaction mass to 10-15C. A solution of aq. acetic acid (30.2 mL, 3.1 eq.) in water (175 mL, 5 V) was added to above reaction mass. The reaction mass was stirred for 30 min. at 20-25C. The organic layer and aq. Layer were separated. The organic layer was kept aside. The aqueous layer was extracted with dichloromethane (70 mL x 4, 2V x 4). [Collectively organic layers were concentrated to get a compound of formula (16) wherein the Rl is specifically methyl]. After dichloromethane wash, adjusted the pH of aqueous layer using aq. ammonia (3V). The aqueous layer was extracted with dichloromethane (70 mL chi 4, 2V chi 4). All the DCM layers were pooled to gather and washed with brine. DCM was removed under reduced pressure at 60C and 50 torr. Added methanol (70 mL, 2V) to reaction mass and refluxed for 1 h and cooled to 35-40C. Distilled methanol under reduced pressure to displace DCM till the temperature reached at 60C at 50 torr the distillation was stopped and continued heating for 1 h. Added methanol (35 mL, IV) to reaction mass and refluxed for 1 h to prepare homogeneous reaction mass. Cooled reaction mass to 20-25C and unload the methanolic solution of product. Yield range: 80-90 %; HPLC purity > 99.00 %; chiral HPLC purity: 100 %,

Statistics shows that 702-82-9 is playing an increasingly important role. we look forward to future research findings about 3-Aminoadamantan-1-ol.

Reference:
Patent; HIKAL LIMITED; MOHILE, Swapnil Surendra; TAPKIR, Sandeep Rameshrao; PATIL, Manoj Vinayak; GANGOPADHYAY, Ashok Kumar; NIGHTINGALE, Peter David; WO2015/128718; (2015); A1;,
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Application of 57772-50-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 57772-50-6 as follows.

Example 4: An aromatic amino alcohol of formula II (R1 = R2 = R4 = R5 = hydrogen, R3 = 3-methyl, 13.48 g, 98 mmol) was dissolved in a THF/diethoxymethane mixture (1 :1, v:v) (73 g) and charged with water (93 g). The agitated brown mixture was cooled to about 12 C. A parallel dosage of gaseous phosgene (13.7 g, 139 mmol) and 25% aqueous NaOH (62.9 g, 393 mmol) was performed within 1 h wherein the pH was kept between 8 and 9 and the temperature in the reaction vessel was kept at 7 to 17 0C. At the end of the phosgene addition the reaction mixture was additionally agitated for 1 h at 12 C. After workup procedure according to example 1 and drying 100% of compound of formula I (R1 = R2 = R3 = R4 = R5 = hydrogen, 16.19 g) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57772-50-6, its application will become more common.

Reference:
Patent; LONZA LTD; GRIFFITHS, Gareth-John; LORENZI, Miriam; WARM, Aleksander; WO2010/115640; (2010); A1;,
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Reference of 6850-65-3, 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. 6850-65-3, name is 4-Aminocyclohexan-1-ol(isomers mixture), 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.

To a solution of 4-aminocyclohexanol (23 g,0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)20 (87 g, 0.4 mol). The resulting solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water (2 x 200 mL) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using DCMI MeOH (V:V, 20:1) to afford the desired product as a white solid. MS: 216.2 (M+1).

According to the analysis of related databases, 6850-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10626; (2015); A1;,
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