Category: alcohols-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 33420-52-9, 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, 33420-52-9, blongs to alcohols-buliding-blocks compound. Recommanded Product: 33420-52-9

To a cooled (0 C) solution of 2,2-difluoropropan-1-ol (193 mg, 2.010 mmol) and pyridine (0.163 mL, 2.010 mmol) in CH3CN (20 mL) was added dropwise Tf2O (0.312 mL, 1.849 mmol). The reaction was maintained at 0 C for 30 min. To a suspension of 5-((2-(benzyloxy)-4,6-dimethylpyridin-3-yl)methyl)-3-methyl- 2-(1-(piperidin-4-yl)propyl)-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one (208 mg, 0.402 mmol) and K2CO3 (500 mg, 3.62 mmol) in CH3CN (20 mL) was added the above cold reaction mixture (containing 2,2-difluoropropyl trifluoromethanesulfonate). The reaction was allowed to warm to RT, then heated to 50 C overnight. The reaction was filtered and evaporated to dryness under vacuum. The residue was dissolved in EtOAc and the resultant solution was washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum to give an oil. A solution of the above oil in TFA (5 mL, 64.9 mmol) was maintained for 30 min, at which time it was concentrated. The reaction mixture was purified by preparative HPLC (5 to 60% MeCN: water with 0.1 % formic acid). The product containing fractions were treated with 6 M HC1 (0.5 mL) and concentrated to give 2-(1-(1-(2,2- difluoropropyl)piperidin-4-yl)propyl)-5-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3- yl)methyl)-3-methyl-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one (90 mg, 0.169 mmol, 42.1% yield) as white solid. 1H NMR (400 MHz, MeOH-d4) delta 7.07 (s, 1H), 4.82 (s, 2H), 3.88-3.99 (m, 2H), 3.72-3.86 (m, 3H), 3.65 (d, J=12.63 Hz, IH), 3.07-3.27 (m, 4H), 2.80- 2.91 (m, IH), 2.69 (s, 3H), 2.54 (s, 3H), 2.40 (s, 2H), 2.27 (d, J=14.15 Hz, IH), 2.00 (ddd, J=3.79, 7.20, 13.52 Hz, IH), 1.57-1.89 (m, 7H), 1.47 (ddd, J=7.07, 11.18, 13.58 Hz, IH), 0.80 (t, J=7.33 Hz, 3H). MS(ES) [M+H]+ 506.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (112 pag.)WO2016/66697; (2016); A1;,
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Reference of 16545-68-9, 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. 16545-68-9, name is Cyclopropanol, molecular formula is C3H6O, 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.

2,6-dichloro-9-cyclopropylpurine2,6-Dichloropurine (1 mmol), triphenylphosphine (1.3 mmol), tetrahydrofurane (5 ml) and cyclopropanol (5 mmol) were stirred at it under nitrogen to give clear yellowish solution, which was then cooled to 0 C and diisopropyldiazadicarboxylate (DIAD; 1.3 mmol) was added via syringe. The reaction mixture was then stirred at rt for 12 h. After evaporation of the solvents the product was extracted with diethylether and purified by column chromatography (silicagel, 1% MeOH in CHCl3). Crystallization from methanol gave the product in yield 35 %, mp 121-124 C.

According to the analysis of related databases, 16545-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERZITA PALACKEHO V OLOMOUCI; BIOPATTERNS s.r.o.; ZATLOUKAL, Marek; KRYSTOF, Vladimir; HAVLICEK, Libor; POPA, Igor; DOLEZAL, Karel; STRNAD, Miroslav; WO2010/139289; (2010); 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 2240-88-2, name is 3,3,3-Trifluoropropan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3,3,3-Trifluoropropan-1-ol

Example 91 6-[5-Bromo-6-(3,3,3-trifluoro-propoxy)-pyridin-2-ylmethyl]-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridin-7-ylamine 6-(5-Bromo-6-fluoro-pyridin-2-ylmethyl)-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridin-7-ylamine (example 22) (45.0 mg, 0.13 mmol), 3,3,3-trifluoro-propan-1-ol (151.8 mg, 1.33 mmol)) and cesium carbonate (108.4 mg, 0.33 mmol) are dissolved in 1.0 mL of tetrahydrofuran. and stirred at 120¡ã C. for 15 minutes. The reaction mixture is concentrated under reduced pressure and the residue is purified by RP-HPLC (modifier: ammonium hydroxide). Yield: 36 mg (62percent of theory) HPLC (Method 5): Retention time=0.89 min.; m/z=431, 433 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 2240-88-2.

Reference:
Patent; Boehringer Ingelheim International GmbH; GODBOUT, Cedrickx; TRIESELMANN, Thomas; VINTONYAK, Viktor; (84 pag.)US2018/37594; (2018); A1;,
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Electric Literature of 702-82-9, 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. 702-82-9, name is 3-Aminoadamantan-1-ol. A new synthetic method of this compound is introduced below.

Compound (S)-1-(2-chloroacetyl) pyrrolidine-2-carbonitrile (12.1 g, 70.3mmol) is added to dichloromethane (200mL), stir for 10 minutes, hydroxyl adamantanamine (12.7 g, 66.8mmol) is slowly added to the above solution, the resulting solution is stirred at room temperature for 10 minutes, Potassium carbonate (19. 3g, 140mmol) is added to the reaction solution, the reaction is stirred for 4 hours.The reaction solution has been filtered, the filter cake is washed with dichloromethane (50mL), combined filtrates. Rotate the solvent to get dryness, the residual oil is added to ethyl acetate to dissolve. The resulting ethyl acetate solution is washed with water (50mL X 2), dry over anhydrous sodium sulfate for 2 hours. The desiccant has been removed; and dried then obtained the crude compound 6 (21.2g).Vildagliptin crude (21. 2g) is added into the reactor which is containing 100mL 2-butanone. The mixture is heated to reflux (95 C) and stirred for 30 minutes. The mixture is filtered into a preheated (75 C) reactor; the filter cake is washed with using hot 2-butanone (100mL). The filtrate is heated to reflux for 30 minutes, slowly cool down at room temperature. Let stand overnight. The system is cooled with an ice water bath for 1 hour. The resulting suspension is filtered, the filter cake is washed twice with 2-butanone.The filter cake has been dried, and obtained target product Vildagliptin 12. 4g(white crystal), 61.3%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,702-82-9, its application will become more common.

Reference:
Patent; Shenzhen Hanyu Pharmaceutical Co., Ltd.; Liu Feimeng; Fang Yihua; Liu Jian; Ma Yaping; Yuan Jiancheng; (10 pag.)CN105884669; (2016); A;,
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Electric Literature of 100-37-8, Adding some certain compound to certain chemical reactions, such as: 100-37-8, name is 2-(Diethylamino)ethanol,molecular formula is C6H15NO, 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 100-37-8.

Valsartan 1.75 g (4.25 mmol),Dichloromethane 30mL,0.49 g (4.25 mmol) of 2- (diethylamino) ethanol was added to the reaction flask,After warming to reflux, 0.34 mL (4.25 mmol) of thionyl chloride,Reaction for 1 hour,HPLC detection reaction was complete,After treatment, the reaction mixture was evaporated to dryness under reduced pressure,Cooled to room temperature by adding 5mL of water,With sodium hydroxide solution to adjust pH = 9 ~ 10,Extract with 30 mL of dichloromethane,The combined organic layers were dried over anhydrous sodium sulfate,2.10 g of Compound (II) concentrated by filtration under reduced pressure were filtered off with a desiccant,Yield 92.5%.

According to the analysis of related databases, 100-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kebeiyuan (Beijing) Bio-pharmaceutical Technology Co., Ltd.; Beijing Zhiyuan Technology Co., Ltd.; Liu Qi; Cheng Zengjiang; (46 pag.)CN107468685; (2017); A;,
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Electric Literature of 57641-67-5, 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 57641-67-5, name is 2-(2-(2-Bromoethoxy)ethoxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Potassium carbonate (916 mg, 6.6 mmol) was added to the solution of imidazole (375 mg, 5.5 mmol) and oligoethylene glycolic bromide (4a-e, 5.5 mmol) in acetone (30 mL) at 25 C. The residue was dissolved in water (50 mL) and extracted from the aqueous phase with EtOAc (50 mL¡Á3). The organic layer was dried (sodium sulfate) and evaporated under reduced pressure. The residue was purified by flash column chromatography (10% MeOH/CH2Cl2) to afford the corresponding oligoethylene glycolic imidazole (5a-e).

According to the analysis of related databases, 57641-67-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jadhav, Vinod H.; Kim, Ju-Young; Chi, Dae Yoon; Lee, Sungyul; Kim, Dong Wook; Tetrahedron; vol. 70; 2; (2014); p. 533 – 542;,
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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. 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate, the common compound, a new synthetic route is introduced below. SDS of cas: 13674-16-3

EXAMPLE 116 (R)-2-[4-(6-Cyano-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-3-phenyl-propionic acid Prepared from 11-(4-hydroxy-phenyl)-benzo [b]naphtho[2,3-d]thiophene-6-carbonitrile (Example 44) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: mp 145-148 C.: [a]D25=-2.03 (7.883 mg/mL CHCl3); NMR (CDCl3); delta8.31 (ddd, J=8, 1, 1 Hz, 1 H), 7.78 (ddd., J=8, 1, 1 Hz, 1 H), 7.70 (ddd, J=8, 8, 1 Hz, 1 H), 7.56 (ddd, J=8, 1, 1 Hz, 1 H), 7.47-7.37 (m, 6 H), 7.32 (ddd, J=8, 7, 1 Hz, 1 H), 7.20 (dd., J=8, 2 Hz, 1 H),7.14-7.05 (m, 4 H), 6.62 (ddd, J=8, 1, 1 Hz, 1 H), 5.06 (dd, J=7, 5 Hz, 1 H), 3.44 (d, J=5 Hz, 1 H), 3.42 (d, J=7 Hz, 1 H); MS (EI): [M+], 499 (100%); Anal. Calc. for C32H21NO3S: C, 76.93, H, 4.24, N, 2.80. Found: C, 75.77, H, 4.22, N, 2.70.

The synthetic route of 13674-16-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US6110962; (2000); A;,
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Electric Literature of 627-30-5 ,Some common heterocyclic compound, 627-30-5, molecular formula is C3H7ClO, 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.

EXAMPLE 10 2-(3-Chloropropoxy)tetrahydropyran To a solution of 3-chloropropanol (20.00 g, 0.212 mol) in dichloromethane (100 mL) 3,4-dihydro-2H-pyran (16.02 g, 0.190 mol) diluted in dichloromethane (17 mL) is added dropwise at 0-5C. The mixture is stirred for 30 minutes and the reaction (checked by TLC analysis) is quenched by washing with saturated sodium bicarbonate (100 mL). After separation the organic layer is washed with water (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure at 30C (34.32 g). The title compound is isolated by column chromatography on silica gel eluding with n-hexane:ethyl acetate) (31.28 g, 0.175 mol, 91%). 1H-NMR {300 MHz, CDCl3, delta (ppm)}: 1.2-2.0 (6H); 2.09 (m, 2H, CH2); 3.56 (m, 2H, Cl-CH2); 3.70 (m, 2H, O-CH2); 3.92 (m, 2H, O-CH2); 4.65 (m, 1 H, O-CH-O). GC-MS (El): [M-H]+ = 177; [M-ClCH2CH2CH2O]+ = 85

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,627-30-5, its application will become more common.

Reference:
Patent; Newchem S.p.A.; EP2019114; (2009); A1;,
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Electric Literature of 111-90-0, 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 111-90-0, name is Diethylene Glycol Monoethyl Ether. This compound has unique chemical properties. The synthetic route is as follows.

59-1) Synthesis of 2-(2-ethoxyethoxy)ethyl 4-methylbenzenesulfonate 432 mg (3.22 mmol) of 2-(2-ethoxyethoxy)ethanol was dissolved in 40 ml of dichloromethane, and 0.6 ml (4.19 mmol) of triethylamine and 614 mg (3.22 mmol) of p-toluenesulfonyl chloride were added thereto. The mixture was stirred at room temperature for 15 hours. After the solvent was removed under reduced pressure, 40 ml of water was added thereto. The mixture was extracted with 30 ml of ethyl acetate. The solvent was removed under reduced pressure to give 760 mg (2.64 mmol) of the title compound in a yield of 82%. 1H NMR (CDCl3, ppm): delta 1.20(3H, t), 2.35(3H, s), 3.35(2H, q), 3.52(2H, t), 3.57-3.60(4H, m), 4.08(2H, t), 7.33(2H, d), 7.78(2H, d) FAB MS(m/e)=289 [M+1]

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 111-90-0, Diethylene Glycol Monoethyl Ether.

Reference:
Patent; Lee, Jin-Ho; Hong, Chang-Yong; Park, Tae-Sik; Kim, Jong-Hyun; Choi, Sei-Hyun; Yoon, Sook-Kyung; Chung, Hyun-Ho; Jeong, Shin-Wu; Hwang, Kwang-Yeon; Shin, Dong-Kyu; US2003/149034; (2003); A1;,
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Electric Literature of 75853-18-8, 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. 75853-18-8, name is 2,3-Difluorobenzyl alcohol. A new synthetic method of this compound is introduced below.

Example 218: 4-[2-(2,3-Difluorobenzyloxy)ethyl]piperidine-l-carboxylic acid tert-butyl esterA stirred solution of (2,3-difluorophenyl)methanol (50 mg, 350 mumol) in anhydrous THF (2 mL) was treated with tBuOK (47 mg, 42 mumol) and then 4-(2-methanesulfonyloxy- ethyl)piperidine-l-carboxylic acid tert-butyl ester (Preparation 10) was added. The resulting mixture was heated under reflux for 12 h, cooled and poured into saturated aqueous NH4Cl, and extracted with EtOAc (20 mL). The organic phase was washed with brine (5 mL), dried (MgSO4) and evaporated. The residue was purified by column chromatography (IH-EtOAc, 4: 1) to afford the title compound: RT = 4.39 min; m/z (ES+) = 356.1 [M+ H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75853-18-8, 2,3-Difluorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; PROSIDION LIMITED; WO2007/3962; (2007); A2;,
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