Month: July 2021

Reference of 16308-92-2 , The common heterocyclic compound, 16308-92-2, name is (2,4-Dimethylphenyl)methanol, molecular formula is C9H12O, 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 7 Synthesis of Dmb protected 6-mercaptohexanoic acid 7 Compound 7 was synthesized according to the following scheme: To a solution of 6-mercaptohexanoic acid (7.10 g, 47.90 mmol) in trifluoroacetic acid (20 mL), 2,4-dimethylbenzyl alcohol (13.5 g, 95.80 mmol) was added. The mixture was stirred at rt for 60 min and then the trifluoroacetic acid was removed in vacuo. The residue was dissolved in a mixture of 95.8 mL LiOH (3 M) and THF (81 mL) and stirred at rt for 60 min. The solvent was removed in vacuo and the aqueous residue was extracted 3x with EtOAc (200 mL). The combined organic phases were dried over MgSO4, and the solvent was removed in vacuo.7 was purified by RP-HPLC. Yield: 2.27 g (8.52 mmol, 18 %) MS: m/z 267.01 = [M+H]+ , (calculated monoisotopic mass = 266.13).

The synthetic route of 16308-92-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASCENDIS PHARMA GROWTH DISORDERS A/S; SPROGØE, Kennett; RAU, Harald; CLEEMANN, Felix; HERSEL, Ulrich; RASMUSSEN, Caroline Elisabeth; (244 pag.)WO2017/118703; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 109240-30-4, 1-(4-Bromophenyl)cyclopropanol, 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, 109240-30-4, blongs to alcohols-buliding-blocks compound. Formula: C9H9BrO

A 5-mL vial was charged with N,N-bis(4-methoxybenzyl)-5-(((3S)-3-(l- propyn-l-yl)-l-piperazinyl)sulfonyl)-2-pyridinamine (0.128 g, 0.246 mmol, Intermediate C), RuPhos palladacycle/RuPhos (1 : 1) (0.033 g, 0.028 mmol, Strem Chemical Inc., Newburyport, MA), l-(4-bromophenyl)cyclopropanol (0.0903 g, 0.424 mmol, Bioorg. Med. Chem. Lett., 2010, 20, 887), sodium 2-methylpropan- 2-olate (0.0702 g, 0.730 mmol, Strem Chemical Inc., Newburyport, MA) and 1,4- dioxane (2 mL). The mixture was degassed by bubbling Ar through the mixture for 5 min. The vial was sealed and the mixture was heated at 100 C for 55 min. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (20 mL). The combined organic phases were washed with saturated aqueous sodium chloride (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under a vacuum. The crude product was purified by column chromatography (25 g of silica, 0 to 50% EtOAc in hexanes) to afford 0.0139 g of light yellow residue. A 5 mL microwave vial was charged with this residue (0.0139 g, 0.021 mmol), and TFA (0.5 mL). Trifluoromethanesulfonic acid (0.025 mL, 0.28 mmol, Alfa Aesar, Ward Hill, MA) was added and the mixture was stirred at room temperature for 5 min. Solid NaHC03 was added followed by aqueous saturated NaHC03. The aqueous phase was extracted with EtOAc (2 x 3 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under a vacuum. The crude product was purified by column chromatography (10 g of silica, 30 to 90% EtOAc in hexanes) to afford l-(4- ((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-( 1 -propyn- 1 -yl)- 1 – piperazinyl)phenyl)-l-propanone (0.0070 g) as a white solid. 1H NMR (300MHz, CD3OD) delta ppm 8.30 (d, J= 2.3 Hz, 1 H), 7.89 (d, J= 9.1 Hz, 2 H), 7.73 (dd, J= 2.5, 9.1 Hz, 1 H), 7.00 (d, J= 9.1 Hz, 2 H), 6.61 (d, J = 8.9 Hz, 1 H), 4.78 (br. s., 1 H), 3.82 – 3.61 (m, 3 H), 3.24 (br. s., 1 H), 2.95 (q, J = 7.3 Hz, 2 H), 2.73 (dd, J= 3.2, 11.5 Hz, 1 H), 2.57 (dt, J= 3.1, 11.7 Hz, 1 H), 1.75 (d, J= 2.2 Hz, 3 H), 1.15 (t, J= 7.3 Hz, 3 H). m/z (ESI, +ve ion) 413.2 (M+H)+. GK-GKRP IC50 (Binding) = 0.353 muMu.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109240-30-4, its application will become more common.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; FOTSCH, Christopher H.; KUNZ, Roxanne K.; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark H.; SIEGMUND, Aaron C.; ST. JEAN, JR., David J.; TAMAYO, Nuria A.; YANG, Kevin C.; WO2014/35872; (2014); A1;,
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Synthetic Route of 4704-94-3, 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. 4704-94-3, name is 2-(Hydroxymethyl)propane-1,3-diol, molecular formula is C4H10O3, 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.

Step A. To a solution of 2-(hydroxymethyl)-1,3-propanediol (1 g, 9.4 mmol) in pyridine (7.5 mL) at 0 C. was added acetic anhydride (0.89 mL, 9.4 mmol) slowly. The resulting solution was warmed to room temperature and stirred for 16 h. The reaction was concentrated under reduced pressure and chromatographed by eluding with methanol-dichloromethane (1:9) to give 510 mg of pure 2-acetoxymethyl-1,3-propanediol.

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 4704-94-3, 2-(Hydroxymethyl)propane-1,3-diol.

Reference:
Patent; Metabasis Therapeutics, Inc.; US6054587; (2000); A;,
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Application of 4720-29-0 ,Some common heterocyclic compound, 4720-29-0, molecular formula is C10H15NO, 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 N-benzylpropanolamine (3.3 g) and benzyl(S)-(+)-glycidyl ether (3.6 g) in ethanol (40 mL) was heated at 40 C. for 18 h. The solvent was evaporated under reduced pressure to give the subtitled compound as a colourless oil (6.8 g, 100%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): delta 7.29 (m, 10H), 4.54 (m, 1H), 4.45 (s, 2H), 4.36 (t, 2H), 3.76 (m, 1H), 3.44 (m, 5H), 2.47 (m, 4H), 1.57 (m, 2H).

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. 4720-29-0, 3-(Benzylamino)-1-propanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; LONN, Hans Roland; CONNOLLY, Stephen; SWALLOW, Steven; KARLSSON, Staffan PO; AURELL, Carl-Johan; PONTEN, John Fritiof; DOYLE, Kevin James; VAN DE POEL, Amanda Jane; JONES, Graham Peter; WATSON, David Wyn; MACRITCHIE, Jaqueline Anne; PALMER, Nicholas John; US2015/210655; (2015); A1;,
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Reference of 100442-33-9, 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 100442-33-9 as follows.

Example 1: Preparation of crude l,4-dihvdro-2,6-dimethyl-4-(3- nitrophenyl)-3 ,5 -pyridinedicarboxylic acid [2-|Y3,3- diphenylpropyl)methylamino~|- 1,1 -dimethyl ethyl] methyl ester hydrochloride (crude lercanidipine hydrochloride)2.31 mL of triethylamine and 2.4 mL of diethylchlorophosphate were added to 5.0 g of 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-l,4- dihydropyridine-3-carboxylic acid (2) in 50 mL of toluene. The mixture was stirred at room temperature for one hour. After formation of a substituted phosphonoester derivative (5) as an intermediate was confirmed by thin layer chromatography (TLC), 4.49 g of 2, N-dimethyl-N-(3,3-diphenylpropyl)-l-amino-2-propanol (3) was added thereto (5). The resulting mixture was refluxed for 4 hours. The reaction mixture was treated with activated carbon and was then concentrated under reduced pressure to remove toluene therefrom. The residue was dissolved in 30 mL of ethyl acetate. The organic phase was washed sequentially with 11 mL of a 10% NaOH aqueous solution, 11 mL of distilled water, 13.1 mL of 6N HCl and 11 mL of distilled water. An organic layer was separated, dried with activated carbon and anhydrous sodium sulfate for 30 min and concentrated under reduced pressure. The residue was dissolved in 15.7 mL of tetrahydrofuran and was then seeded with 50 mL of lercanidipine hydrochloride. The lercanidipine hydrochloride (dispersion) was stirred at 20 to 25 C for 24 hours, filtered and dried under vacuum to obtain 8.3 g of crude lercanidipine hydrochloride (theoretical yield: 85.1%).IH NMR (DMSO-d, 400MHz) (ppm): 10. 8 -9.4 (bb, IH), 9.5 (bs, IH), 8.30 – 8.05 (m, 2H), 7.85 -7.60 (m, 2H), 7.55 -7.20 (m, 10H), 5.05 (s, IH), 4.15 – 3.35 (m, 6H), 3.20 -2.15 (m, 13H), 2.6 (s, 3H), 1.50 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100442-33-9, its application will become more common.

Reference:
Patent; DONGWOO SYNTECH CO., LTD; WO2008/82041; (2008); 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.6850-39-1, name is 3-Aminocyclohexanol, molecular formula is C6H13NO, molecular weight is 115.17, as common compound, the synthetic route is as follows.Product Details of 6850-39-1

C. tert-butyl(3-Hydroxycyclohexyl)carbamate To a solution of 3-aminocyclohexanol (3.0 g, 26.0 mol) in THF (30 mL) was added di-tert-butyl dicarbonate (6.74 g, 31.2 mmol). The resulting mixture was stirred at 50 C. for 16 h. Then the reaction mixture was concentrated in vacuum and purified by silica gel column chromatography (30% ethyl acetate in petroleum ether) to afford the desired compound (4.40 g, 20.46 mmol, 78% yield). MS (ESI) m/z 216.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6850-39-1, 3-Aminocyclohexanol, and friends who are interested can also refer to it.

Reference:
Patent; Papa, Patrick; Cathers, Brian Edwin; CALABRESE, Andrew Antony; WHITEFIELD, Brandon Wade; BENNETT, Brydon; CASHION, Daniel; MORTENSEN, Deborah; HUANG, Dehua; TORRES, Eduardo; PARNES, Jason; SAPIENZA, John; HANSEN, Joshua; LEFTHERIS, Katerina; CORREA, Matthew; DELGADO, Maria Mercedes; RAHEJA, Neil; BAHMANYAR, Sami; HEGDE, Sayee; NORRIS, Stephen; PLANTEVIN-KRENITSKY, Veronique; US2015/175557; (2015); A1;,
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Application of 22348-44-3, 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. 22348-44-3, name is trans-4-(Methylamino)cyclohexanol, molecular formula is C7H15NO, 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.

EXAMPLE 17 trans 1-(4-Hydroxy-cyclohexyl)-3-(4-methoxy-7-[1,4]dioxepan-6-yl-benzothiazol-2-yl)-1-methyl-urea Using 7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-ylamine, phenyl chloroformate and trans-4-methylamino-cyclohexanol, the title compound was prepared as off-white solid. MS: m/e=452(M+H+).

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 22348-44-3, trans-4-(Methylamino)cyclohexanol.

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/235915; (2004); A1;,
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Electric Literature of 22436-06-2, 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 22436-06-2, name is (S)-2-Methyl-3-phenylpropan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen protection,Add to a 1L three-neck glass bottle54g of (±)-2-methyl-3-phenyl-1-propanol,64g of phthalic anhydride,1.38 g of pyridine,540 g of tetrahydrofuran.The reaction was stirred at 0 C – 20 C for 30 hours.Concentrated to give 122 g of crude material.After crystallization with ethyl acetate as a solvent,Obtained 103g of (±)-2-methyl-3-phenyl-1-propanol- phthalic acid monoester,The purity of the liquid chromatography is ?98%.

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 22436-06-2, (S)-2-Methyl-3-phenylpropan-1-ol.

Reference:
Patent; Jiangsu Guangyu Chemical Co., Ltd.; Diao Bozhen; Zhang Limeng; Kang Jie; (13 pag.)CN109534957; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 111-46-6, 2,2′-Oxybis(ethan-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, Recommanded Product: 2,2′-Oxybis(ethan-1-ol), blongs to alcohols-buliding-blocks compound. Recommanded Product: 2,2′-Oxybis(ethan-1-ol)

A solution of diethylene glycol (5.01 g, 47.21 mmol), / olucncsulfonyl chloride (4.50 mg, 23.6 mmol) and triethylamine (8.55 mL, 61.37 mmol) in DCM (200 mL) was stirred at 25 C for 16 h. The reaction was added to FLO (30 mL) and extracted with DCM (2 x 50 mL). The organic layer was separated, dried with over Na2S04 and concentrated under vacuum. The residue was purified by silica gel chromatography (petroleum ether :EtO Ac 10:1 to 1 : 1) to afford 2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate (2.95 g, 40%) as a light yellow oil; LC-MS 283.0 [M+Na]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111-46-6, 2,2′-Oxybis(ethan-1-ol), and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BENZ, Joerg; GRETHER, Uwe; HORNSPERGER, Benoit; KOCER, Buelent; KUHN, Bernd; RICHTER, Hans; TSUCHIYA, Satoshi; BELL, Charles; WU, Xiang; YAN, Xiaofei; GOBBI, Luca; (188 pag.)WO2019/105915; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 307353-32-8, Methyl 3-bromo-5-(hydroxymethyl)benzoate, 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, 307353-32-8, blongs to alcohols-buliding-blocks compound. Application In Synthesis of Methyl 3-bromo-5-(hydroxymethyl)benzoate

Step 1 (0579) Compound iii-51 (300mg, 1.22mmol), (2,4-difluorophenyl)boronic acid (290mg, 1.84mmol), PdCl2 (dppf) (90mg, 0.12mmol) and potassium phosphate (780mg, 3.67mmol) were dissolved into toluene (12mL) under nitrogen atmosphere under microwave irradiation, and the mixture was stirred at 140C for 30 minutes. After the reaction mixture was filtrated by Celite, the solvent was removed in vacuo. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give Compound iii-52 (304mg, 89%). 1H-NMR (CDCl3) delta: 8.09-8.05 (m, 2H), 7.72 (d, J = 1.5 Hz, 1H), 7.46-7.40 (m, 1H), 7.00-6.91 (m, 2H), 4.82 (d, J = 5.8 Hz, 2H), 3.94 (s, 3H), 1.83 (t, J = 5.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,307353-32-8, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; KAWASUJI, Takashi; MIKAMIYAMA, Hidenori; SUZUKI, Naoyuki; MASUDA, Koji; SUGIMOTO, Hideki; OKANO, Azusa; YOSHIDA, Miho; SUGIYAMA, Shuichi; ASAHI, Kentarou; KOZONO, Iori; MIYAZAKI, Keisuke; OZASA, Hiroki; MIYAGAWA, Masayoshi; (374 pag.)EP3192794; (2017); A1;,
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