Month: September 2021

Synthetic Route of 870-72-4 ,Some common heterocyclic compound, 870-72-4, molecular formula is CH3NaO4S, 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 16 200 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide trihydrate and 65.2 g of sodium hydroxymethanesulfonate were suspended in 400 ml of water, and the suspension was refluxed over night. After cooling, the reaction mixture was washed with chloroform, and an insoluble material was removed by filtration. The filtrate was concentrated in vacuo. The residue was dissolved in a mixture of 500 ml of water and 500 ml of ethanol under heating, and then the solution was cooled. The precipitate formed was collected by filtration and recrystallized from a mixture of water and ethanol to give 59.2 g of sodium N-(3-carbamoylphenyl)-N-(2-((2-(3,4-dimethoxyphenyl)ethyl)amino)-2-oxoethyl)aminomethanesulfonate dihydrate as colorless crystals with m.p. 253 to 255 C. (decomposition). Analysis for C20 H24 N3 O7 SNa.2H2 O: Calcd: C 47.15, H 5.54, N 8.25. Found: C 47.11, H 5.39, N 8.34. NMR (DMSO-d6): delta: 2.57 (2H, t, 6 Hz), 3.4-3.1 (2H, br), 3.67 (6H, s), 4.05 (2H, br), 4.29 (2H, br), 6.47-7.33 (8H, m), 7.75 (1H, br), 8.26 (1H, br).

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. 870-72-4, Hydroxymethanesulfonic Acid Sodium Salt, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Daiichi Pharmaceutical Co., Ltd.; US4985595; (1991); A;,
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Reference of 431-38-9, 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. 431-38-9, name is 3-Amino-1,1,1-trifluoropropan-2-ol. A new synthetic method of this compound is introduced below.

Into a microwave vial under an inert atmosphere of N2, were placed intermediate from Step B (220 mg, 0.40 mmol), in N-methyl-2-pyrrolidinone (3 mL) and THF (3 mL), and 3-amino-1,1,1-trifluoropropan-2-ol (207 mg, 1.60 mmol). The mixture wasirradiated with microwave radiation at 180 C for 3 h, then cooled to RT, quenched with water (100 mL), and extracted with EtOAc (3 x 100 mL). The combined organic layer was washed with water (2 x 100 mL), dried over anhydr. Na2SO4, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography with MeOH/DCM (0- 5%) to afford the racemic title compound, which was resolved by chiral-prep-HPLC ColumnPhenomenex Lux 5u Cellulose-4, to afford isomers A (faster eluting) and B (slower eluting) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,431-38-9, 3-Amino-1,1,1-trifluoropropan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WHITEHEAD, Alan; ORNOSKI, Olga; RAGHAVAN, Subharekha; BERGER, Raphaelle; GARFUNKLE, Joie; YANG, Zhiqiang; JI, Gang; JIANG, Falong; FU, Jianmin; (132 pag.)WO2017/197555; (2017); 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. 10160-24-4, name is 7-Bromo-1-heptanol, the common compound, a new synthetic route is introduced below. Product Details of 10160-24-4

General procedure: The alkyl bromide (1.0 equiv) was added to a solution of mercaptoaceticacid (1.0 equiv) in methanol (10.0 mL) and the resultingsolution stirred. Then a solution of NaOH (2.0 equiv) in methanol(5.0 mL)was added slowly, and the final mixturewas stirred at roomtemperature or heated to reflux until absence of the alkyl bromide(checked by TLC). The reaction mixture was concentrated in vacuo,diluted with H2O, and neutralized with 1 N HCl. Then the obtainedreaction mixture was extracted with EtOAc. The combined organicfractions were washed with brine, dried with Na2SO4, and concentratedin vacuo. Purification of the crude residue by column chromatography(petroleum ether/EtOAc) afforded the title compound.

The synthetic route of 10160-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Ying; Wu, Bolin; Hao, Yameng; Liu, Yunqi; Zhang, Zhili; Tian, Chao; Ning, Xianling; Guo, Ying; Liu, Junyi; Wang, Xiaowei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 420 – 433;,
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Electric Literature of 22436-06-2 , The common heterocyclic compound, 22436-06-2, name is (S)-2-Methyl-3-phenylpropan-1-ol, molecular formula is C10H14O, 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: Methanesulfonyl chloride (6.29 mmol) was added dropwise to asolution of the alcohol (5.72 mmol) and diisopropylethylamine (8.58 mmol) in DCM (20.5 mL) at 0 C and warmed to room temperature. After 90 min, the mixture was partitioned with distilled water (2*20 mL), 1M HCl (2*10 mL), and brine (20 mL). The organic layer was dried (MgSO4), filtered, and concentrated under vacuum to give the desired compound, which was taken forward without purification

The synthetic route of 22436-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shouksmith, Andrew E.; Evans, Laura E.; Tweddle, Deborah A.; Miller, Duncan C.; Willmore, Elaine; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Australian Journal of Chemistry; vol. 68; 4; (2015); p. 660 – 679;,
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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.945-24-4, name is (2,4-Diaminopteridin-6-yl)methanol, molecular formula is C7H8N6O, molecular weight is 192.18, as common compound, the synthetic route is as follows.HPLC of Formula: C7H8N6O

2,4,5,6-Tetraminopyrimidine.H2SO4.H2O (75.0 g, 0.293 mole) was added to a stirred solution of BaCl2.2H2O (71.5 g, 0.293 mole) in H2O (1.45 l.) at 85-90 C. The mixture was stirred rapidly at about 90 C. for 15 min, cooled to 40 C., and filtered from BaSO4, which was washed thoroughly on a funnel with H2O. The clear, yellow filtrate was then diluted further with H2O to give a volume of 4.35 l. This solution of the tetraminopyrimidine.2HCl was then added to a solution of NaOAc (4.35 l. of 4 N) in which dihydroxyacetone (79.3 g, 0.88 mole) and cysteine.HCl.H2O (51.5 g, 0.293 mole) had just been dissolved. The resulting solution was stirred mechanically at room temperature while a slow stream of air was continuously passed through it for 26 hr. (Yellow-orange solid began separating after 2 hr.) The mixture was then kept in a refrigerator for 16 hr before the solid was collected, washed successively with cold H2O, EtOH, and Et2O before it was dried to constant weight in vacuo over P2O5 at 25 C. [The crude product mixture (47 g) was weighed in order to obtain an estimate of the volume of 48% HBr required to form hydrobromide salts.] A mechanically stirred mixture of the dried solid and EtOH (6.05 l.) was heated to 70 C., and a solution of 48% HBr (28 ml) in EtOH (490 ml) was added in a thin stream while the mixture was maintained at 70-75 C. The mixture was then refluxed for about 5 min with rapid stirring while nearly all of the solid dissolved. The hot solution was treated with Norit and filtered through a Celite mat. The clear yellow filtrate was kept in a refrigerator overnight while a first crop of orange-colored solid separated. The collected solid was washed with EtOH, then dried in vacuo (56 C. over P2O5) to give 17.2 g of product. The filtrate was concentrated by evaporation (rotary evaporator, H2O aspirator, bath to 35 C.) to about 2 l. and then refrigerated to give a second crop, which was dried as before, of 10.2 g; total yield 27.4 g (34%). The 1H NMR spectrum of this material in CF3CO2D showed it to contain a barely detectable amount of methyl substituted 2,4-diaminopteridine.HBr as evidenced by very weak signals at 62.83 (CH3) and 68.85 (pteridine ring H). Strong signals produced by the desired product occur at delta5.28 (6-CH2O) and 69.08 (C7-H). The proportion of desired product to the methyl-substituted contaminant was estimated from the 1H NMR integrals to be 20:1. The 1H NMR spectrum also revealed retention of a small amount of EtOH in the product dried as described but not enough to interfere with the conversion of it to 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,945-24-4, (2,4-Diaminopteridin-6-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Kamen, Barton; Cole, Peter; Smith, Angela; Zebala, John A.; US2005/209239; (2005); A1;,
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Electric Literature of 23377-40-4, Adding some certain compound to certain chemical reactions, such as: 23377-40-4, name is 3-(Hexadecyloxy)propan-1-ol,molecular formula is C19H40O2, 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 23377-40-4.

Compound 2 (658 mg, 1.74 mmol) was added to the reaction flask.Add 10 ml of anhydrous dichloromethane to dissolve.Nitrogen protection drops to 0 C,Compound 1 (631 mg, 2.1 mmol) was slowly added dropwiseAnd pyridine (826 mg, 10.44 mmol)Anhydrous dichloromethane solution.After the addition, the reaction was carried out at a low temperature for 10 minutes, and then the reaction was continued to room temperature for 2 hours.MS monitors the reaction,The reaction was quenched by the addition of 1 M diluted hydrochloric acid (10 mL).Stir at room temperature overnight,After MS monitors the reaction, the organic phase is separated.The aqueous phase was extracted 2-3 times with dichloromethane.Combine the organic phase,Washed with saturated saline,Concentration and purification by silica gel column chromatography gave 815.3 g of product, yield: 82.3%.

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. 23377-40-4, 3-(Hexadecyloxy)propan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Zhao Jiuyang; (46 pag.)CN109485676; (2019); A;,
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Reference of 28539-02-8, 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 28539-02-8 as follows.

To a 4 ml ethanol solution of 220 mg of 3-amino-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one was added 105 mg of 1H-1,2,3-benzotriazol-1-ylmethanol, followed by overnight stirring at room temperature. Next, 48 mg of sodium borohydride was added to the reaction mixture, followed by stirring for 3 hours. By adding water to the resulting reaction mixture and collecting the insoluble materials by filtration, 100 mg of 7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-3-(methylamino)quinolin-4(1H)-one was obtained.

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; Astellas Pharma Inc.; EP1995240; (2008); A1;,
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Application of 929-06-6 ,Some common heterocyclic compound, 929-06-6, molecular formula is C4H11NO2, 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.

Add a magnet to a 1L round bottom flask.Add (9.542 ml, 95.1113 mmol),Dichloromethane 150ml dissolved,Triethylamine (26.5133 ml, 190.2226 mmol) was added,Boc anhydride was added under stirring (24.9096 g,114.1335mmol). After the reaction was completed, the reaction solution was transferred to a rotary evaporator and concentrated. Methanol was added to dissolve the mixture. Under stirring, sodium bicarbonate powder (13 g) was added to neutralize triethylamine, suction filtered, and silica gel powder was added as a solid solution. Dry method,Column chromatography eluting with a gradient of 10% ethyl acetate/petroleum ether to 50% ethyl acetate/petroleum ether, gradient elution with 3% methanol/ethyl acetate to 6% methanol/ethyl acetate.The product was collected and evaporated to give 16.3341 g of compound in a yield of 83.77%.

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. 929-06-6, 2-(2-Aminoethoxy)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chongqing A Pugelei Biological Technology Co., Ltd.; Li Gaoquan; Chen Maofen; Wang Bin; Li Dajun; Zhang Qian; Shui Juyuan; Peng Liangyan; Huang Lei; He Tingting; Zhang Cuifang; Wu Xiaodan; Li Jianhuan; (39 pag.)CN107670050; (2018); A;,
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Synthetic Route of 3279-95-6 ,Some common heterocyclic compound, 3279-95-6, molecular formula is C2H7NO2, 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.

1.10 (2) Preparation of Final Compound 1-64 and 1-65 A mixture of intermediate of example 1.10(1) (350 mg, 0.76 mmol), 2-aminooxy-ethanol (CAS No. 1025727-45-0) (292. mg, 3.801 mmol) and pyridine (10 mL) in ethanol (25 mL) was stirred at 70 C. for 5 days. The solvent was removed under reduced pressure. The crude residual fraction was purified by high-performance liquid chromatography (RP-18) (eluent: Gradient:[0.25% NH4HCO3 in H2O]/CH3CN 90/10-20/80-0/100 v/v). The desired fractions were collected and evaporated to dryness. This product was further purified by HPLC on Hyperprep C18 HS BDS 100 A 8 mu (Shandon) (eluent: 60%[0.25% NH4HCO3 in H2O]/40% CH3CN, then the column was rinsed with 100% CH3CN), yielding 168 mg (42%) of compound 1-65 (the E isomer) and 57 mg (14%) of compound 1-64 (the Z isomer).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3279-95-6, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2012/35171; (2012); A1;,
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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. 55489-58-2, name is 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol, molecular formula is C13H20O4, 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. category: alcohols-buliding-blocks

General procedure: Methanesulfonyl chloride (1.5 equiv.) was added drop-wise to astirred solution of alcohol (1 equiv.) and Et3N (1.5 equiv.) in anhydrousDCM (30 mL) at 0 C under nitrogen. The reaction wasallowed to warm to room temperature, and stirred for 2 h. Thereaction mixture was poured into methanol (10 mL), and concentratedin vacuo. The reaction mixture was then diluted with diethylether (20 mL), washed with water (3 20 mL) and brine(3 20 mL). The combined organic extracts were then dried overanhydrous MgSO4, filtered, and concentrated in vacuo. The residuewas dissolved in DMF (25 mL), sodium azide (3 equiv.) was added, and the mixture was stirred at 60 C for 16 h. The reaction mixturewas concentrated in vacuo, and The reaction mixture was thendiluted with diethyl ether (50 mL), washed with water (3 20 mL)and brine (3 30 mL), dried over anhydrous MgSO4, filtered, andconcentrated in vacuo, to give a residue which was purified by flashchromatography.

With the rapid development of chemical substances, we look forward to future research findings about 55489-58-2.

Reference:
Article; Suthagar, Kajitha; Watson, Andrew J.A.; Wilkinson, Brendan L.; Fairbanks, Antony J.; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 153 – 166;,
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