Month: February 2021

Application of 431-38-9 ,Some common heterocyclic compound, 431-38-9, molecular formula is C3H6F3NO, 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.

A solution of 150 mg intermediate 6-[4-(trifluoromethoxy)phenyl]-2-(3-fluorophenyl)-3-oxo-2,3- dihydropyridazine-4-carboxylic acid, 90.2 mg 3-amino-1 ,1 ,1 -trifluoro-2-propanol, 260.4 mg HATU, 0.18 mL ethyldiisopropylamine and 2 mg 4-dimethylaminopyridine in 2.5 mL of DMF was stirred at room temperature for 3 hours. Then the reaction mixture was filtered and subjected to RP-HPLC (Instrument: Labomatic HD-3000 HPLC gradient pump, Labomatic Labocol Vario-2000 fraction collector; column: Chromatorex C-18 125 mm x 30 mm, eluent A: 0.1 % formic acid in water, eluent B: acetonitrile; gradient: A 60% / B 40%? A 20% / B 80%; flow: 150 mL/min; UV-detection: 254 nm) to yield 101 mg 2-(3-fluorophenyl)-3-oxo-N-(3,3,3- trifluoro-2-hydroxypropyl)-6-[4-(trifluoromethoxy)phenyl]-2,3-dihydropyridazine-4-carboxamide. 1H NMR (400 MHz, DMSO-d6) delta ppm = 3.47 (ddd, 1 H), 3.70 – 3.81 (m, 1 H), 4.18 – 4.28 (m, 1 H), 6.66 (d, 1 H), 7.36 – 7.44 (m, 1 H), 7.51 (d, 2 H), 7.54 – 7.59 (m, 1 H), 7.59 – 7.67 (m, 2 H), 8.10 (d, 2 H), 8.69 (s, 1 H), 9.64 (t, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,431-38-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); SCHMEES, Norbert; GUTCHER, Ilona; IRLBACHER, Horst; BADER, Benjamin; ZHAO, Na; PLATTEN, Michael; (437 pag.)WO2017/202816; (2017); A1;,
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Synthetic Route of 13674-16-3, 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 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 194 (R)-2-[2-Bromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-6-methoxy-phenoxy]-3-phenyl-propionic acid Prepared from 2-bromo-4-(6-bromo-benzo [b]naphtho [2,3-d]thiophen-11-yl)-6-methoxy-phenol (Example 193) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96) according to the procedure in Example 113. White solid: mp >103 C. (dec.): NMR (CDCl3); delta8.36 (ddd, J=8, 1, 1 Hz, 1 H), 7.83 (ddd, J=8, 7, 1 Hz, 1 H), 7.67 (ddd, J=8, 7, 1 Hz, 1 H), 7.57-7.26 (m, 9 H), 7.18 (ddd, J=8, 7, 1 Hz, 1 H), 6.89 (ddd, J=8, 1, 1 Hz, 1H), 6.79 (ddd, J=8, 7, 1 Hz, 1H), 5.29 (t, 1H), 3.76, 3.74 (ds, 3 H), 3.39-3.46 (m, 2 H); MS (EI): [M+], 2 bromine isotope pattern, 660; Anal. Calc. for C32H22Br2O4S: C, 58.02, H, 3.35, N, 0.00. Found: C, 58.04, H, 3.73, N, 0.02.

According to the analysis of related databases, 13674-16-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US6110962; (2000); A;,
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Electric Literature of 6971-51-3, 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. 6971-51-3, name is (3-Methoxyphenyl)methanol. A new synthetic method of this compound is introduced below.

General procedure: Geranyl bromide 12a was synthesized from geraniol via the reaction with PBr3.18 PBr3 (8.9 mmol) was added to cooled (0-5C) solution of geraniol (26.7 mmol) in dry ether (30 ml) and the reaction mixture was stirred for 2 h at r.t. Saturated aqueous NaHCO3 was added and the product was extracted with ether. The extracts were washed with brine, dried with Na2SO4 and evaporated. Other used bromides 12b-e were synthesized as described above. Compounds 12a, 12b, 12c and 12e (the yields 91%, 55%, 60% and 65%, respectively) were sufficiently pure and used for the next step without purification. The compound 12d was purified by column chromatography on SiO2, eluent – hexane (yield 24%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6971-51-3, (3-Methoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Khomenko, Tatyana M.; Zarubaev, Vladimir V.; Orshanskaya, Iana R.; Kadyrova, Renata A.; Sannikova, Victoria A.; Korchagina, Dina V.; Volcho, Konstantin P.; Salakhutdinov, Nariman F.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 13; (2017); p. 2920 – 2925;,
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Adding a certain compound to certain chemical reactions, such as: 1562-00-1, Sodium isethionate, 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, Computed Properties of C2H5NaO4S, blongs to alcohols-buliding-blocks compound. Computed Properties of C2H5NaO4S

To an one liter autoclave were added 600 mL of 24% ammonium hydroxide solution, 126 g of sodium isethionate, and 2.0 g of sodium hydroxide. The solution was heated to250 C. for 2 hours. To the solution was added 64 g of ammonium chloride. Afier complete removal of ammonia from the solution by heating, the pH of the solution became 7-8. Afier concentrating and cooling, 98 g of crystalline taurine was obtained by filtration in a yield of 78.4%.

The synthetic route of 1562-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAWORKS IP, LLC; Hu, Songzhou; (5 pag.)US9850200; (2017); B1;,
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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. 3973-18-0, name is Propynol ethoxylate, the common compound, a new synthetic route is introduced below. SDS of cas: 3973-18-0

[Synthesis 8]Production of 2,4,6-triisopropyl-N-((lR,2R)-2-(2-((4-methylcyclohexa-l,4-dienyl)methoxy)etheyl amino)- l,2-diphenylethy)benzenesulfonamide In 25 ml of toluene, 6.03 g (18.82 mmol) of the above-described tosylates obtained in Synthesis 7 were dissolved. To this solution, 2.43 g (18.82 mmol) of DIPEA and 9.00 g (18.80 mmol) of (R,R)-TIPPsDPEN were added, foUowed by stirring at 135C for 13 hours. After that, the solvent was removed by distillation under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate=20/l>15/l). Thus, 10.53 g of the title compound was obtained as a colorless oily substance. Yield: 89.0%. ?-NMR (CDCI3, 300 MHz) 5:1.06 (d, J=6.9 Hz, 3H), 1.21 (d, J=6.9 Hz, 3H), 1.87 (brs, 1H), 1.68 (s, 3H), 2.60 (brs, 4H), 2.71-2.48 (m, 2H), 3.52-3.34 (m, 2H), 3.55 (d, J=8.9 Hz, 1H), 3.77 (s, 2H), 3.95 (septet, J=6.7 Hz, 3H), 4.40 (d, J=8.9 Hz, 1H), 5.44 (m, 1H), 5.64 (m, 1H),6.52 (brs, 1H), 6.74-7.28 (m, 12H);HRMS(ESI):[M+H]+ calcd for C39H53N2O3S: 629.3771; found: 629.3771

The synthetic route of 3973-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKASAGO INTERNATIONAL CORPORATION; TANAKA, Shigeru; TOUGE, Taichiro; NARA, Hideki; ISHIDA, Kenya; WO2013/65867; (2013); A1;,
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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. 16369-21-4, name is 2-(Propylamino)ethanol. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H13NO

PREPARATION EXAMPLE 8 N-[2-(1-Adamantyloxy)ethyl]propylamine hydrochloride (Intermediate No. 8-1) 2-(Propylamino)ethanol (2.4 g, 23 mmol) was mixed with 1-bromoadamantane (0.50 g, 2.3 mmol) and triethylamine (0.32 ml, 2.3 mmol), and the mixture was stirred at an external temperature of 100 C. for two hours, at 130 C. for five hours and at 150 C. for three hours. The reaction mixture was allowed to stand, then ethyl acetate (50 ml) was added to the reaction mixture, and the whole was washed with water (50 ml) twice and saturated brine (30 ml) successively. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, a 4 N solution of hydrogen chloride in ethyl acetate (2 ml) was added to the separated substance, and the whole was concentrated under reduced pressure. The resulting crystals were filtered off with ethyl acetate to give 0.16 g (25%) of the titled compound as colorless crystals. IR(KBr): 3544, 2907, 2502, 1584 cm-1 mp: 232.0-232.7 C.

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, 16369-21-4, 2-(Propylamino)ethanol.

Reference:
Patent; Ban, Masakazu; Suhara, Hiroshi; Horiuchi, Masato; Yamamoto, Noriyoshi; Enomoto, Hiroshi; US2003/32623; (2003); 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.62058-03-1, name is trans-4-Aminoadamantan-1-ol, molecular formula is C10H17NO, molecular weight is 167.25, as common compound, the synthetic route is as follows.Application In Synthesis of trans-4-Aminoadamantan-1-ol

General procedure: To a solution of ethyl 1-phenyl-5-(2-methyl-4-oxobutan-2-yl)-1H-pyrazole-4-carboxylate 14b (45 mg, 0.15 mmol) in CHCl3 (9 mL) was added trans-5-hydroxy-2-adamantylamine (25 mg, 0.15 mmol), acetic acid (0.025 mL, 0.45 mmol) and sodium triacetoxyborohydride (85 mg, 0.45 mmol) at room temperature. After stirring at ambient temperature for 16 hours, the reaction mixture was quenched with aq. NaHCO3, extracted with CHCl3, and washed with aq. NaCl. The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in methanol (0.30 mL), and added 1.0 N NaOH (0.22 mL, 0.22 mmol) at room temperature. After stirring at ambient temperature for 16 hours, the solvent was removed under vacuum. The mixture of the residue in CHCl3 (1.5 mL) and DIPEA (0.078 mL, 0.45 mmol) and HBTU (35 mg, 0.15 mmol) was stirred at room temperature. After 16 hours, the reaction mixture was quenched with aq. NaHCO3, extracted with CHCl3, and washed with aq. NaCl., then purified with column chromatography (silica gel, eluting with CHCl3/methanol) to give the title compound as a white solid (0.025 g, 42 percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62058-03-1, trans-4-Aminoadamantan-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Udagawa, Shuji; Sakami, Satoshi; Takemura, Takahiro; Sato, Mikiya; Arai, Takahiro; Nitta, Aiko; Aoki, Takumi; Kawai, Koji; Iwamura, Tomokatsu; Okazaki, Seiji; Takahashi, Takehiro; Kaino, Mie; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1617 – 1621;,
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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. 623-04-1, name is (4-Aminophenyl)methanol. A new synthetic method of this compound is introduced below., Recommanded Product: 623-04-1

Intermediate 10: tert-butyl 4-(hydroxymethyl)phenylcarbamateTo a solution of p-aminobenzyl alcohol (38,2 mmol) in 100 ml dioxane were added triethylamine (114 mmol) and di-tert-butyldicarbonate (42,0 mmol) was added in portions. The mixture was stirred overnight at room temperature. The solvent was evaporated. EtOAc was added and washed with 2N HCI, saturated NaHCO3 and brine solution. The organic layer was dried over Na2SO4 and evaporated to yield a brown oil.Yield: 82 %, MS (ESI) m/z 224.3 [M+H]1H-NMR (ODd3, 400 MHz) 51.54 (s, 9H), 4.65 (s, 2H), 6.54 (s, 1H), 7.22-7.43 (m, 4H).

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, 623-04-1, (4-Aminophenyl)methanol.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; JOOSSENS, Jurgen; AUGUSTYNS, Koen; LAMBEIR, Anne-Marie; VAN DER VEKEN, Pieter; VAN SOOM, Jeroen; MAGDOLEN, Viktor; (66 pag.)WO2015/144933; (2015); A1;,
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Application of 16545-68-9 ,Some common heterocyclic compound, 16545-68-9, molecular formula is C3H6O, 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: 1-bromo-5-cyclopropyloxy-2-methyl-4-nitrobenzene 1-bromo-5-fluoro-2-methyl-4-nitrobenzene (70g , 0.3mol), freshly prepared cyclopropanol diethyl ether complex (23g, ?0.4mol) and N, N- dimethylformamide (260mL) were added into a 500mL reaction flask. Sodium tert-butoxide (35g, 0.36mol) was added slowly thereinto at 0Cand the reaction mixture was stirred at 0C for 1.5 hours. After completion of the reaction, the reaction mixture was poured into ice water slowly, and the precipitated solid was filtered to obtain the crude product. The filter cake was then washed with a lot of water and dried through air to obtain the title compound (yellow solid, 78g, 96%), which may be used directly for the subsequent reaction. (MS: [M+1] none)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16545-68-9, its application will become more common.

Reference:
Patent; Beijing Pearl Biotechnology Limited Liability Company; DONG, Jiaqiang; ZHONG, Boyu; YUAN, Hongbin; SHI, Quan; CHU, Shaosong; ZHANG, Deyi; ZHANG, Ruihao; (219 pag.)EP3150592; (2017); A1;,
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Synthetic Route of 6351-10-6 , The common heterocyclic compound, 6351-10-6, name is 2,3-Dihydro-1H-inden-1-ol, molecular formula is C9H10O, 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.

General procedure: The acetates were synthesized by classical chemical acetylations via the corresponding racemic alcohol (1 equiv), using 1.5 equiv of anhydride acetic, 1.2 equiv of Et3N, and a catalytic amount of 4-dimethylaminopyridine (0.1 equiv) in 4 ml of ether. The acetates were obtained pure after standard work-up. The 1H NMR spectra of these products were in good agreement with the literature.

The synthetic route of 6351-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Merabet-Khelassi, Mounia; Houiene, Zahia; Aribi-Zouioueche, Louisa; Riant, Olivier; Tetrahedron Asymmetry; vol. 23; 11-12; (2012); p. 828 – 833;,
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