Category: alcohols-buliding-blocks

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.19064-18-7, name is (2,6-Difluorophenyl)methanol, molecular formula is C7H6F2O, molecular weight is 144.12, as common compound, the synthetic route is as follows.Product Details of 19064-18-7

A solution of 2 ml (18.0 mmol) (2,6-difluorophenyl) methanol in 15 ml at 0 C stirred dry tetrahydrofuran was treated with 865.9 mg (6.21 mmol) of sodium hydride (60% in mineral oil), followed by 1.72 ml (18.0 mmol) of 2-bromopyridine.The solution was stirred at room erature for 15 hours.The reaction mixture was diluted (15 ml) with water and extracted with dichloromethane (2 x 20 ml).The organic phase was separated, dried with a phase separation cartridge, and concentrated in vacuo.The residue was purified by flash chromatography using a prepacked silica gel cartridge purified, yielding 800 mg of the target compound (eluent: 1 cyclohexane-ethyl acetate 10: 1 to 1) (15% of theory, 77%. purity).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19064-18-7, (2,6-Difluorophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAF; VAKALOPOULOS, Alexandros; FOLLMANN, Markus; BUCHGRABER, Philipp; HARTUNG, Ingo; LINDNER, Niels; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, TOBIAS; REDLICH, Gorden; DIETZ, Lisa; LI, Volkhart Min-Jian; (391 pag.)TW2016/5850; (2016); A;,
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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. 110-73-6, name is 2-(Ethylamino)ethanol, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(Ethylamino)ethanol

1.0 g (11.22 mmol) of 2- (ethylamino) ethanol,10 mL of acetonitrile,0.77 g (5.61 mmol) of potassium carbonate was added to the reaction flask,Warmed to 60 C,A solution of 1.98 g (11.22 mmol) of benzyl bromide and 10 mL of acetonitrile was added dropwise for 15 min.Continue to react for 30 minutes,HPLC detection reaction was complete,After treatment, the reaction solution was evaporated to dryness,Add 20mL water,Extraction with ethyl acetate,The combined organic phases were dried over anhydrous sodium sulfate,Of 1.47 g of a brown oil (II)Yield 75.0%.

The synthetic route of 110-73-6 has been constantly updated, and we look forward to future research findings.

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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Reference of 534-03-2, Adding some certain compound to certain chemical reactions, such as: 534-03-2, name is 2-Aminopropane-1,3-diol,molecular formula is C3H9NO2, 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 534-03-2.

General procedure: To a stirred mixture of serinol 8 (1 equivalent) and K2CO3 (3 equivalents) in DMSO at 70-80 oC wasadded the appropriate fluoroaromatic 7d-f in portions over 5 minutes. The resulting colouredmixture was stirred (typically 3 hours), allowed to cool to room temperature, and then poured intoice-water with stirring. The resulting diol 9c-f was collected, washed with water and allowed to dry inair.

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. 534-03-2, 2-Aminopropane-1,3-diol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chappel, Lucy; Leong, Chee-Onn; Mai, Chun-Wai; Meikle, Ian T.; Stanforth, Stephen P.; Truong, Thang V.; Wong, Lai Chun; Bioorganic and medicinal chemistry letters; (2019);,
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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.100058-61-5, name is 3-(Benzyloxy)cyclobutanol, molecular formula is C11H14O2, molecular weight is 178.23, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks

Step 2. 3-(benzyloxy)cyclobutyl methanesulfonate [0641] A 100-mL round-bottom flask was charged with 3-(benzyloxy)cyclobutanol (1.83 g, 10.3 mmol), dichloromethane (20 mL) and triethylamine (2.15 mL, 15.4 mmol), and the solution was cooled to 0 C. Methanesulfonyl chloride (1.20 mL, 1.77 g, 15.4 mmol) was added dropwise, and the resulting solution stirred for 30 min at 0 C. The reaction mixture was poured into water (30 mL) and extracted with dichloromethane (2 x 30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-(benzyloxy)cyclobutyl methanesulfonate (2.60 g, 99%) as a light yellow solid. MS (ESI, pos. ion) m/z 257[M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100058-61-5, 3-(Benzyloxy)cyclobutanol, and friends who are interested can also refer to it.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
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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 100-86-7, name is 2-Methyl-1-phenyl-2-propanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H14O

REFERENCE EXAMPLE 2 1,3,3-trimethyl-3,4-dihydroisoquinolin To conc. sulfuric acid (10 ml) was added a solution of 2-methyl-1-phenylpropan-2-ol (7.0 g) and acetonitrile (1.62 ml) in benzene (7.0 ml) dropwise and the mixture was stirred for 24 hours at room temperature.The mixture was neutralized by adding to a mixture of ice and a saturated aqueous solution of sodium bicarbonate dropwise, and it was extracted with ethyl acetate twice.The extract was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure.The residue was dissolved in ether and was extracted with 1 N hydrochloric acid and 2N hydrochloric acid.The extract was washed with ether and to the mixture was added 5N aqueous solution of sodium hydroxide and was extracted with ether twice.The extract was washed with water and a saturated aqueous solution of sodium chloride successively, and dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to give the title compound (2.53 g) having the following physical data. TLC: Rf 0.22 (hexane:ethyl acetate=2:1); NMR (CDCl3): delta 7.48 (dd, J=7.5, 1.5 Hz, 1H), 7.35 (dt, J=1.5, 7.5 Hz, 1H), 7.30-7.25 (m, 1H), 7.14 (d, J=7.5 Hz, 1H), 2.69 (s, 2H), 2.38 (s, 3H), 1.20 (s, 6H).

With the rapid development of chemical substances, we look forward to future research findings about 100-86-7.

Reference:
Patent; Ogawa, Mikio; Takaoka, Yoshikazu; Ohhata, Akira; US2004/77643; (2004); A1;,
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Synthetic Route of 83647-43-2 ,Some common heterocyclic compound, 83647-43-2, molecular formula is C8H9BrO, 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.

Step B: 5-Bromo-4-methyl-2-benzofuran-l(3H)-one: To a flask charged with (3-bromo-2- methylphenyl)methanol (6.0 g, 30 mmol) was added a 1M TFA solution of ThalliumTrifluoroacetate (16.2 g, 29.8 mmol). The mixture was stirred at RT overnight. The solvent was removed under vacuum, and the residue was pumped under high vacuum for 30 min to ensure complete removal of TFA. To the residue was then added palladium(II) chloride (529 mg, 2.98 mmol), lithium chloride (2.53 g, 59.7 mmol), magnesium oxide (2.41 g, 59.7 mmol), and MeOH (150 mL). The reaction was flushed with CO twice, and kept under CO at RT. Analysis by LC showed a formation of product within 2 hours. To this solution was added ethyl acetate to precipitate the salts. The solution was filtered through a celite pad, washed with EtOAc, adsorbed onto silica and purified by silica gel chromatography to provide the title compound

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. 83647-43-2, (3-Bromo-2-methylphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; PIO, Barbara; CHOBANIAN, Harry, R.; WO2013/62900; (2013); A1;,
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Related Products of 34626-51-2 , The common heterocyclic compound, 34626-51-2, name is 5-Bromopentan-1-ol, molecular formula is C5H11BrO, 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.

[00149] 5-bromo-l-pentanol (1), 3g, is treated with 1.5 eq of 3, 4-dihydro-2H-pyran and 0.1 eq of pyridinium para toluenesulfonate (PPTS) in 135mL of CH2CI2. Other starting materials, such as bromo C1.9 alcohols may be used to obtain other embodiments of compounds of formula VII. [00150] After work -up and purification, 1.45 g (33%) of product 2 is obtained. 1.0 eq of methyl malonitrile is deprotonated with 1 eq of NaH and 1.0 eq of bromide 2 is added along with catalytic amount of KI at 50C. A complete conversion can be observed after 10 hours and a 90% yield can be obtained. Deprotection of tetrahydo pyran (THP) can be done with PPTS in ethanol at 55C. After work-up, a quantitative yield of alcohol 4 is obtained and directly used for the mesylation reaction. With the mesylate 5 in hand, a kryptofix- mediated fluorination can be performed. Compound 6 is obtained in 68% yield. 12mL of DMF, 10 eq. of acetic acid, triethylamine and sodium azide each are added to compound 6. The resulting mixture is stirred at 140C for 19 hours. Water and IN HC1 are added. The solid is filtered off and washed with water. Compound 7 is obtained in a 60% yield. [00151] NMR [for example, Bruker Avance 400 (400 MHz, CDC13, TMS as internal standard] of the 5,5′(7-fluoroheptane-2,2-diyl)bis(lH-tetrazole) compound shows the following results: delta 1.29 (m, 4H, CH2), 1.49 (m, 2H, CH2), 1.77 (s, 3H, Me), 1.87 (t, 2H, CH2), 4.09 (m, 2H, CH2F).

The synthetic route of 34626-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APOSENSE LTD.; VAN GELDER, Joel M.; LEVY, Menashe; ARGOV, Mirit; BEN-AMI, Miri; ZIV, Ilan; WO2013/150534; (2013); A1;,
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Reference of 722-92-9, Adding some certain compound to certain chemical reactions, such as: 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol,molecular formula is C9H7F6NO, 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 722-92-9.

Example 500 2-Acetyl-5-(cyclopropylsulfamoyl)-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-2,3-dihydro-1H-isoindole-1-carboxamide DIPEA (0.162 mL, 0.92 mmol) was added to 2-acetyl-5-(cyclopropylsulfamoyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid (100 mg, 0.31 mmol), 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (88 mg, 0.34 mmol) and HATU (129 mg, 0.34 mmol) in DCM (5 mL) under nitrogen. The resulting solution was stirred at room temperature for 1 hour. The reaction mixture was quenched with saturated NH4C1 (20 mL), extracted with DCM (3*20 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford dark solid. The crude product was purified by flash silica chromatography, elution gradient 0 to 100percent EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford 2-acetyl-5-(cyclopropylsulfamoyl)-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-2,3-dihydro-1H-isoindole-1-carboxamide (40.0 mg, 22.94percent) as a colorless solid. LC/MS: m/z=566 [M+H]+. HRMS: calculated for (C23H21F6N3O5S+H)+566.1184. found (ESI [M+H]+) 566.1185. 1H NMR (400 MHz, DMSO-d6, mixture of rotamers, 4.5*:1) delta 0.36-0.54 (m, 4H), 1.99, 2.15*(s, 3H), 2.08-2.10 (m, 1H), 4.76-4.93, 5.00-5.09*(m, 2H), 5.71*, 5.91 (s, 1H), 7.61-7.70 (m, 3H), 7.71-7.82 (m, 3H), 7.84-7.92 (m, 1H), 8.00, 8.02*(d, 1H), 8.67*, 8.69 (s, 1H), 10.71*, 10.94 (s, 1H).

According to the analysis of related databases, 722-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Synthetic Route of 115652-52-3, 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 115652-52-3 as follows.

8.3 [1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol (III-4) 1.4 g (II) are placed in 10 ml dioxane, first 3.6 ml diisopropylethylamine, then 1 g of 1-aminocyclopropanmethanol (see 8.2) are added. The reaction mixture is heated to 160 C. until there is no further reaction and after cooling evaporated down. The residue is treated with cyclohexane/ethyl acetate (8:2) in the ultrasound bath and the solid is suction filtered and dried. 1.24 g (III-4) are obtained as a solid. Analytical HPLC-MS (method A): RT=1.01 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115652-52-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; Nickolaus, Peter; US2013/237527; (2013); A1;,
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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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, the common compound, a new synthetic route is introduced below. SDS of cas: 722-92-9

To a solution of 4( 1 hydroxy-1 rifluoromethyl2,2,24ritiuoroethyl)aniline (60mg, 0.232 mmol) in CH2CI2 (2 mL) were successively added at RT N,Ndiisopropylethylamine (80 pL, 0.463 mmol) and 2chlorobenzoyl chloride (41 pL, 0.324 mmd). The mixture was stirred for 3 h and concentrated under reduce pressure. The crude residue was directly purified by cdumn chromatography on siNca gel without any workup by hexane/AcOEt (812) to obt&n 65 mg (71percent) 0 SR987 as a white powder: FTR cm1 3338. 3028, 1643, 1521, 1410; 1254. 1219, 1188, 1112, 968, 944, 826; 1H NMR (400 MHz, MeODd4) S =797 (t, J = 1.8 Hz, 1 H), 7.91 7.86 (m, I H), 7.85 7.80 (m, 2 H), 7.75 7.70 (m, 2 H),7.63 7.58 (m, I H), 7.51 (t, J 7.8 Hz, 1 H); 13C NMR (101 MHz, MeODd4) S = 167.5,141.5, 138.2, 135.9, 133.1, 131.4, 129.0 (2C), 128.9, 128.5, 127.3 (2C), 121.7 Thereare tree carbons msshg for the descdpton of SR1078. They correspond to the three carbons of the (1 hydroxy- 1 trmuoromethy2 2 ,24fiuoroethy) moety. The fluodne coupng with these carbons gkte muWpets that are very dUflcuft to see on the ?3C spectrum even with a proonged number of scans. HRMS (ES) m/z [M+H] c&cd for C16H10CF6NO2, 398.0377; found, 398.0395; Mp = 170A72C.

The synthetic route of 722-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; GRIFFIN, Patrick; KAMENECKA, Theodore; CHANG, Mi, Ra; DOEBELIN, Christelle; (58 pag.)WO2017/79120; (2017); A1;,
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