Author: tianli

Application of 14320-38-8 ,Some common heterocyclic compound, 14320-38-8, molecular formula is C5H8O, 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 1: Intermediate 1 [00819j A solution of the compound cyclopent-3-enol (1.5 g, 17.9 mmol) in 10 mL of DMF was cooled to 0 C and to the mixture was added TBDPSC1 (7.35 g, 26.8 mmol), imidazole (3.6 g, 53.6 mmol) and DMAP (0.2 g, 1.8 mmol) under N2. The mixture was stirred at 28 C under N2 overnight afterwhich itwas quenched through addition of saturated aqueous NaHCO3, extracted with EtOAc, dried and evaporated to dryness. (5.0 g, 87 %). ?H NMR (400 MHz, CDC13): oel.08 (s, 9H), 2.32-2.5 1 (m, 4H), 4.54-4.59 (m, 1H) 5.62 (s, 2H), 7.35-7.46 (m, 6H), 7.68 (dd, 4H).

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. 14320-38-8, Cyclopent-3-enol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SANOFI; D’AGOSTINO, Laura Akullian; SJIN, Robert Tjin Tham; NIU, Deqiang; MCDONALD, Joseph John; ZHU, Zhendong; LIU, Haibo; MAZDIYASNI, Hormoz; PETTER, Russell C.; SINGH, Juswinder; BARRAGUE, Matthieu; GROSS, Alexandre; MUNSON, Mark; HARVEY, Darren; SCHOLTE, Andrew; MANIAR, Sachin; WO2014/144737; (2014); A1;,
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Application of 1227159-85-4, 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. 1227159-85-4, name is (1-(4-Bromophenyl)cyclobutyl)methanol, molecular formula is C11H13BrO, 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-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (260 mg, 1.00 mmol) and N,N-dimethylformiminium chloride (250 mg, 2.00 mmol) in dry dioxane (5 mL) and DMF (1 mL) was sealed in a reaction vessel and stirred at room temperature for 10 minutes to give a white slurry. To the slurry was added 2M aqueous potassium carbonate (2.5 mL, 5.0 mmol), [1-(4-bromophenyl)cyclobutyl]methanol (240 mg, 1.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg). The reaction mixture was degassed with nitrogen and heated to 90 C. for 30 minutes. The reaction was quenched with water (20 mL) and extracted with EtOAc (3*20 mL). The combined organic phases were dried and concentrated in vacuo to give 6-chloro-5-{4-[1-(hydroxymethyl)cyclobutyl]phenyl}-1H-indole-3-carbaldehyde (180 mg, 68% yield), which was used into next step without further purification.

According to the analysis of related databases, 1227159-85-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; Bhattacharya, Samit; Cameron, Kimberly; Dowling, Matthew; Fernando, Dilinie; Ebner, David; Filipski, Kevin; Kung, Daniel; Lee, Esther; Smith, Aaron; Tu, Meihua; US2013/267493; (2013); A1;,
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Related Products of 161446-90-8, 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 161446-90-8, name is 3-Chloro-4-fluorobenzyl Alcohol. This compound has unique chemical properties. The synthetic route is as follows.

Example 222 4- ( (3-Chloro-4-fluorobenzyl) oxy) -1- (2- ( (1RS,2SR) -2- (2- hydroxypropan-2-yl ) cyclopropyl) -l-methyl-lH-benzimidazol-6- yl) pyridin-2 (1H) -one To a mixture of. 4-hydroxy-l- (2- ( ( IRS, 2SR) -2- (2- hydroxypropan-2-yl ) cyclopropyl) -l-methyl-lH-benzimidazol-6- yl) pyridin-2 (1H) -one (100 mg) , (3-chloro-4- fluorophenyl) methanol (95 mg) , tributylphosphine (0.219 ml) and THF (10 ml) was added 1, 1′ – (azodicarbonyl) dipiperidine (223 mg) , and the mixture was stirred at 60C for 2 h. The reaction mixture was diluted with EtOAc, washed with water and brine successively, dried over MgS04, filtered through a plug of NH silica gel, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH) , followed by NH silica gel column chromatography (hexane/EtOAc) . Then the resulting solid was recrystallized from IPA-EtOAc to give the title compound (58.4 mg) as an off-white solid. MS (ESI+) : [M+H] + 482.2. XH NMR (400 MHz, DMSO-d6) : delta 1.09 (6H, s) , 1.23-1.32 (1H, m) , 1.36-1.44 (1H, m) , 1.56-1.66 (1H, m) , 2.22-2.31 (1H, m) , 3.86 (3H, s), 5.18 (2H, s) , 5.86 (1H, s) , 5.98 (1H, d, J = 2.3 Hz), 6.13 (1H, dd, J = 2.3, 7.8 Hz), 7.09 (1H, d, J = 8.4 Hz), 7.35 (1H, d, J = 7.9 Hz), 7.51-7.59 (3H, m) , 7.60-7.70 (2H, m) .

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 161446-90-8, 3-Chloro-4-fluorobenzyl Alcohol.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
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Electric Literature of 4415-73-0, 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 4415-73-0, name is 1,1-Cyclobutanedimethanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of [1-(hydroxymethyl)-cyclobutyl]methanol (2.50 g, 21.5 mmol, 1.0 equiv.) which was prepared as described in the reference (F. X. Tavares et al., J. Med. Chem. 2004, 47, 5057-5068) in CH2Cl2 (43 mL) was added SOCl2 (2.35 mL, 32.3 mmol, 1.5 equiv.) slowly at 0 C. After being stirred for 2 h at 25 C., the reaction was diluted (10% MeOH/CH2Cl2) and washed (1×H2O and 1×brine). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to provide the product as a colorless liquid

According to the analysis of related databases, 4415-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; US2007/299111; (2007); A1;,
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Reference of 616-29-5 ,Some common heterocyclic compound, 616-29-5, molecular formula is C3H10N2O, 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.

The Schiff base ligand, H2L was prepared prepared according to literature method [15]. To prepare the Schiff base ligand, 2-hydroxy-1,3-diaminopropane (0.0890g, 1mmol) was refluxed with O-vanilin (0.3046g, 2mmol) in 20ml dehydrated alcohol for 6h and after 7-10 days yellowish orange colored compound was isolated from solution, which was dried and stored in vaccuo over CaCl2 for subsequent use. Yield: 3.420g (87%). Anal. Calc. for C19H22N2O5 (H2L): IR (KBr, cm-1): 3365 (vOH), 1618 (vC=N), 1333, 1245 (vPhO); UV-Vis (lambdamax, nm): 255, 315, 403; 1H NMR (delta ppm, 400Mz, DMSO-d6) delta=13.55 (s, 2H), 9.92 (s, 2H), 7.26-6.90 (Ar-H, 6H), 5.94 (s, 1H), 3.93 (s, 6H) ppm. EI-MS (m/z) 359.16 [H2L+H+]+ (see Scheme 1).

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. 616-29-5, 1,3-Diaminopropan-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pal, Sukanta; Chowdhury, Biswajit; Patra, Moumita; Maji, Milan; Biswas, Bhaskar; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 144; (2015); p. 148 – 154;,
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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.2566-44-1, name is 2-Cyclopropylethanol, molecular formula is C5H10O, molecular weight is 86.13, as common compound, the synthetic route is as follows.Recommanded Product: 2-Cyclopropylethanol

A. p-Toluenesulfonyl chloride (7.20 g, 37.8 mmol) was added to a cooled (0 C) solution of 2-cyclopropylethanol (4.00 g, 46.4 mmol) in pyridine (10 mL) and dichloromethane (60 mL). The reaction mixture was stirred at ambient temperature overnight, then diluted with ether (200 mL) and washed sequentially with water, 10% HCl, water and brine and then dried over anhydrous Na2SO4. Toluene-4-sulfonic acid 2-cyclopropylethyl ester (8.1 g, 89%) was obtained after removal of solvent and used for next step reaction without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2566-44-1, 2-Cyclopropylethanol, and friends who are interested can also refer to it.

Reference:
Patent; Xenon Pharmaceuticals Inc.; Abreo, Melwyn; Chafev, Mikhail; Chakka, Nagasree; Chowdhury, Sultan; Fu, Jian-Min; Gschwend, Heinz, W.; Holladay, Mark, W.; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Li, Wenbao; Liu, Shifeng; Raina, Vandna; Sun, Sengen; Sun, Shaoyi; Sviridov, Serguei; Tu, Chi; Winther, Michael, D.; Zhang, Zaihui; (94 pag.)EP2316827; (2016); B1;,
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Synthetic Route of 28539-02-8 ,Some common heterocyclic compound, 28539-02-8, molecular formula is C7H7N3O, 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.

To a solution of 2-(4-((6-methoxypyridin-3-yl)oxy)piperidin-1-yl)-3-methylfuro[3,4- b]pyridin-5(7H)-one (70 mg, 0.197 mmol) in THF (3 mL) was added LDA (2.5 M in THF, 0.095 mL, 0.236 mmol) at -78 C under a nitrogen atmosphere. The reaction was stirred at -78 C for 15 min before (1H-benzo[d][1,2,3]triazol-1-yl)methanol (29.4 mg, 0.197 mmol) was added. After 30 min the reaction was quenched with aqueous ammonium chloride (saturated, 5 mL) and was extracted with DCM (10 mL x 3). The combined organic layers were concentrated and purified by reverse phase HPLC (ACN/water with 0.1% NH3OH modifier) to afford the title compound. MS: 386 (M+1).1H NMR (400 MHz, methanol-d4): delta 7.84 (1H, d, J = 2.8 Hz), 7.79 (1H, s), 7.43 (1H, dd, J = 8.8, 2.8 Hz), 6.76 (1H, d, J = 8.8 Hz), 5.34 (1H, s), 4.52-4.54 (1H, m), 4.16 (1H, dd, J = 12.8, 2.8 Hz), 3.95 (1H, dd, J = 4.0, 0.8 Hz), 3.85 (3 H, s), 3.71-3.73 (2 H, m), 3.28-3.35 (2 H, m), 2.38 (3 H, s), 2.11-2.16 (2 H, m), 1.87-1.92 (2 H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,28539-02-8, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GAO, Xiaolei; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; ONDEYKA, Debra, L.; (148 pag.)WO2018/118736; (2018); 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.6338-55-2, name is 2-(2-(2-Aminoethoxy)ethoxy)ethanol, molecular formula is C6H15NO3, molecular weight is 149.1882, as common compound, the synthetic route is as follows.Computed Properties of C6H15NO3

S48 (0.45 g, 3.00 mmol), DIPEA (1.6 mL, 9.00 mmol) were added, dissolving in DMF (20 mL) at -12 C for 30 min in N2. Then S5 (in DMF, 5 mL, 0.71 g, 1.00 mmol) was dropped into this mixture, stirring overnight. After this reaction the solvent was removed, the mixture was dissolved in deionized water (25 mL), then the aqueous was washed by DCM (25 mL) three times. This aqueous dialyzed in deionized water 5 times and freeze-dried to get S49 (1.21 g, 67%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6338-55-2, 2-(2-(2-Aminoethoxy)ethoxy)ethanol, and friends who are interested can also refer to it.

Reference:
Article; Wang, Jue; Qi, Wenjing; Chen, Guosong; Chinese Chemical Letters; vol. 30; 3; (2019); p. 587 – 591;,
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Reference of 30595-79-0, Adding some certain compound to certain chemical reactions, such as: 30595-79-0, name is 2,6-Dichlorophenethyl alcohol,molecular formula is C8H8Cl2O, 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 30595-79-0.

Synthesis Example 20: Compound No.125 (2S,3R,4R,5S,6R)-2-(4-chloro-5-(chroman-6-ylmethyl)-2,3-dihydrobenzofuran-7-yl)-5-fluoro-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4-diol To a mixture of 2-(2,6-dichlorophenyl)ethan-1-ol (200 g, 1.05 mol, 1.00 equiv) in toluene (3500 mL) was added NaH (52.8 g, 2.20 mol, 1.25 equiv, 60% purity). The mixture was stirred for 20 minutes at 40 C. To the resulting solution was then added CuCl (cuprous chloride) (5.21 g, 52.63 mmol, 0.05 equiv) and ethyl acetate (4.63 g, 52.61 mmol, 0.05 equiv). The reaction was stirred for overnight at reflux. Ice water was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2SO4. The mixture was then concentrated and purified by chromatography on silica gel (50:1 PE/EA) to yield 4-chloro-2,3-dihydrobenzofuran as a yellow oil.

According to the analysis of related databases, 30595-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Xu, Guozhang; Kuo, Gee-Hong; Gaul, Micheal; (68 pag.)US2019/55226; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1074-61-9, (4-Vinylphenyl)methanol, 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, COA of Formula: C9H10O, blongs to alcohols-buliding-blocks compound. COA of Formula: C9H10O

Using a reaction scheme adapted from O. Shimomura, et al, Synthesis and application of polytetrahydrofuran-grafted polystyrene (PS-PTHF) resin supports for organic synthesis, Tetrahedron 61 (2005) 12160-12167, phosphorous tribromide (PBr3) (18.4 g, 6.4 ml, 68 mmol) dissolved in ethyl ether (10 ml) was added to 4-vinylbenzyl alcohol (5.9 g, 44.3 mmol) in Et20 (500 ml) at 0C under N2. After 1 hour, additional PBr3 (18.4 g, 6.4 ml, 68 mmol) was added. The reaction mixture was stirred for 1 hour at room temperature and subsequently cooled to 0C. Water (100 ml) was slowly added. The solution was extracted with Et20, and the Et20 layer was washed with aqueous NaHC03, brine and dried with MgS04. The crude product was purified by silica gel column chromatography using a hexane:EtOAc, (70:30) eluent system to obtain product vinyl benzyl bromide. XH NMR (CDC13, 500 MHz) £4.48 (s, 2H), 5.26(d, 1H) 5.76(d, 1H) 6.69-6.75(q, 1H) 7.32(d, 2H) 7.41 (d, 2H). UV-vis [chloroform, max(8)]:215, 260.

The synthetic route of 1074-61-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTH CAROLINA CENTRAL UNIVERSITY; TAYLOR, Darlene K.; BALAMI, Uddhav; WO2015/73882; (2015); A1;,
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