Category: 631-58-3

Application of 631-58-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 631-58-3, name is Propanethioamide, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 28 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridylamine A solution of 2-(2-amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide (125 g, 0.323 mol) and thiopropionamide (28g, 0.314 mol) in N,N-dimethylformamide (1200 mL) was stirred at room temperature for 14 hrs. The solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was poured into the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated. Crude crystals were washed with hexane-ethyl acetate = 1: 1 to give the title compound (76.0 g, yield 82%). melting point: 144-146C.

The chemical industry reduces the impact on the environment during synthesis Propanethioamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1364949; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 631-58-3, A common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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 mixture of propanethioamide ethyl] amino-i -oxo-3 -phenylpropane-2-ylcarbamate (12): A mixture of propanethioamide(69 mg, 0.78 mmol) and (5)-tert-butyl 4-bromo-i-(4-nitrophenyl)-3-oxobutan-2- ylcarbamate, 7, (0.300 g, 0.77 mmol) in CH3CN (4 mL) is refluxed for 2 hours. The reaction mixture is cooled to room temperature and diethyl ether is added to precipitate the intermediate 2-(nitrophenyl)-(5)- 1 -(4-ethylthiazol-2-yl)ethylamine which is isolated by filtration as the hydrobromide salt. The hydrobromide salt is dissolved in DMF (8mL) together with diisoproylethylamine (0.38 mL, 2.13 mmol), i-hydroxybenzotriazole (107 mg, 0.71 mmol) and (5)-(2-methoxycarbonyl-amino)-3-phenylpropionic acid (175 mg, 0.78 mmol). The mixture is stirred at 0 C for 30 minutes then at room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combined organic phase is washed with 1 N aqueous HC1, 5 % aqueous NaHCO3, water and brine, and dried over Na2SO4. The solvent is removed in vacuo to afford 0.300g (81% yield) of the desired product which is used without further purification. LC/MSESI+MS 483 (M+1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AERPIO THERAPEUTICS INC.; PETERS, Kevin; SHALWITZ, Robert; JANUSZ, John; SMITH, Alexander; WO2014/145068; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 631-58-3 as follows. Product Details of 631-58-3

0.40 g (1 .47 mmol) 5-bromo-azepan-4-one hydrobromide, 0.13 g (1 .47 mmol) thiopropionamide and 3 mL ethanol. were stired under reflux for 3 hours. The reaction was allowed to cool to RT and was filtered. The filtrate was concentrated to dryness and dried. Yield: 0.39 g (quantitativ) ESI-MS: m/z = 183 (M+H)+ Rt(HPLC): 0.39 min (Method J)

According to the analysis of related databases, 631-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GOTTSCHLING, Dirk; EBEL, Heiner; RIETHER, Doris; WELLENZOHN, Bernd; WO2013/144172; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 631-58-3, name is Propanethioamide, belongs to amides-buliding-blocks compound, 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 631-58-3, HPLC of Formula: C3H7NS

Process Step [V3]: 4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine (Ex. 41)At room temperature, 1.31 g (14.7 mmol) propanethioamide are added to a solution of 5.00 g (13.3 mmol) of 2-bromo-1-(4-fluorophenyl)-2-(4-pyridyl)ethanone hydrobromide (described, for example, in Chem. Pharm. Bull. 2005, 53, 410-418) in 30 ml of DMF, and the mixture is stirred for 16 h. Subsequently, the reaction mixture is stirred into 100 ml of ice-water, 50 ml of a saturated aqueous Na-HCO3 are added and the mixture is extracted with ethyl acetate (3×100 ml). The combined organic phases are washed with water (2×100 ml), dried over MgSO4 and freed from the solvent under reduced pressure. The crude product is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 2.85 g (75%) of the desired product; 1H-NMR(DMSO-d6) delta: 8.53 (d, 2H), 7.47 (m, 2H), 7.26 (d, 2H), 7.17 (m, 2H), 3.05 (q, 2H), 1.37 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Propanethioamide, and friends who are interested can also refer to it.

Reference:
Patent; Bayer CorpScience AG; US2010/168185; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 631-58-3 as follows. name: Propanethioamide

0.40 g (1 .47 mmol) 5-bromo-azepan-4-one hydrobromide, 0.13 g (1 .47 mmol) thiopropionamide and 3 mL ethanol. were stired under reflux for 3 hours. The reaction was allowed to cool to RT and was filtered. The filtrate was concentrated to dryness and dried. Yield: 0.39 g (quantitativ) ESI-MS: m/z = 183 (M+H)+ Rt(HPLC): 0.39 min (Method J)

According to the analysis of related databases, 631-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GOTTSCHLING, Dirk; EBEL, Heiner; RIETHER, Doris; WELLENZOHN, Bernd; WO2013/144172; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 631-58-3, These common heterocyclic compound, 631-58-3, name is Propanethioamide, 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 mixture of propanethioamide (69 mg, 0.78 mmol) and (S)-tert-butyl 4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-ylcarbamate, 7, (0.300 g, 0.77 mmol) in CH3CN (4 mL) is refluxed for 2 hours. The reaction mixture is cooledto room temperature and diethyl ether is added to precipitate the intermediate 2-(nitrophenyl)-(S)-1-(4-ethylthiazol-2-yl)ethylamine which is isolated by filtration as the hydrobromide salt. The hydrobromide salt is dissolved in DMF (8 mL)together with diisoproylethylamine (0.38 mL, 2.13 mmol), 1-hydroxybenzotriazole (107 mg, 0.71 mmol) and (S)-(2-methoxycarbonyl-amino)-3-phenylpropionic acid (175 mg, 0.78 mmol). The mixture is stirred at 0 C for 30 minutes thenat room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combinedorganic phase is washed with 1 N aqueous HCl, 5 % aqueous NaHCO3, water and brine, and dried over Na2SO4. Thesolvent is removed in vacuo to afford 0.300g (81% yield) of the desired product which is used without further purification.LC/MS ESI+MS 483 (M+1).

Statistics shows that Propanethioamide is playing an increasingly important role. we look forward to future research findings about 631-58-3.

Reference:
Patent; Aerpio Therapeutics, Inc.; PETERS, Kevin, G.; SHALWITZ, Robert; (176 pag.)EP2624916; (2018); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 631-58-3,Some common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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.

Ethyl chloroacetate (1 equiv) was dissolved in dry acetone, and a solution of thiopropanamide (1 equiv) in acetone was added. The reaction was refluxed overnight. After cooling to rt, volatiles were evaporated. The residue was diluted with ethyl acetate followed by careful addition of saturated NaHCO3 (aq). Layers were separated and the aqueous layer was extracted with ethyl acetate (2x), organics were combined, dried (Na2SO^ and concentrated to give a yellow residue. Purification by column chromatography on silica gel (ethyl acetate: hexanes: 80:20) provided (2-Ethyl-thiazol~4-yl)-acetic acid ethyl ester in 45 % yield, m/z (ES+) 200 (M+H4″).

The synthetic route of 631-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; NEUROGEN CORPORATION; WO2006/122200; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 631-58-3, A common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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 stirring solution of 2-(2-chloropyrimidin-4-yl)-1-(3-methyl-5-{[(triisopropylsilyl)oxy]methyl}phenyl)ethanone (2.47 g, 1.0 eq) in DCM (85 ml.) was added NBS (1.07 g, 1.05 eq). After stirring 0.25 h, the reaction mixture was concentrated and taken up in DMF (40 ml.) and treated with thiopropionamide (0.75 g, 1.5 eq). After stirring 1 h, the reaction mixture was quenched with NaHCOs (aq) and extracted 2X with EtOAc. The organic extracts were dried over MgSO4, filtered, concentrated onto silica gel, and purified by column chromatography (gradient elution: 0 to 60% hexane/EtOAc) to provide 0.51 g (26%) of the title compound of Step C; 1H NMR (400 MHz, CDCI3) delta 8.36 (d, J = 5.5 Hz, 1 H), 7.41 (s, 1 H), 7.32 (s, 1 H), 7.28 (s, 1 H), 7.06 (d, J = 5.3 Hz, 1 H), 4.73 (s, 2 H), 3.20 (q, J = 7.5 Hz, 2 H), 2.37 (s, 3 H), and 1.50 (t, J = 7.6 Hz, 3 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 631-58-3 as follows. 631-58-3

Into a solution of Compound 94 (145 mg, 0.33 mmol) in THF (10 mL) at 00 C was added phenyltrimethylammonium tribromide (125 mg, 0.33 mmol). The mixture was stirred at O 0 C for 1 hour, quenched by ice addition, extracted with methylene chloride. The combined extracted was dried (Na2SO4), filtered and concentrated to give crude 75a (200mg).Into a solution of 75a (52 mg, 0.1 mmol) in 3 mL of EtOH was added ethanethioamide (0.2 mmol) at room temperature. The resulting solution was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue was taken up with ethyl acetate. The solution was treated with saturated solution of NaHCO3 and extracted with ethyl acetate. The combined extracts were dried (NaaSClambdai) and concentrated. Column chromatography on silica gel (eluted with 10-70% ethyl acetate in hexanes) gave Compound 95 (40 mg).1H NMR (300 MHz, CDCI3) 510.40 (brs, 1 H), 7.54-7.42 (m, 5H), 7.02 (t, J = 8.5Hz, 2H), 2.65 (s, 3H), 1.90 (s, 3H).MS (ESI) [M+H+]: 496.

According to the analysis of related databases, 631-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2007/87427; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

631-58-3,Some common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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 9 A mixture of 3.6 parts of propanethioamide, 8.6 parts of 2-bromo-1-(4-hydroxyphenyl)ethanone and 79 parts of ethanol was stirred for 7 hours at reflux temperature. The reaction mixture was concentrated to 1/4 of its volume and 2,2′-oxybispropane was added to the residue. The precipitate was filtered off and taken up in water. After basifying with NH4 OH, the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 3.3 parts (40.2%) of 4-(2-ethyl-4-thiazolyl)-phenol (interm. 17).

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

Reference:
Patent; Janssen Pharmaceutica N.V.; US5100893; (1992); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics