Analyzing the synthesis route of 2346-26-1

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

D. 4-[4-(2,4-Dioxo-oxazolidin-5-ylidenemethyl)-2-methoxy-phenoxy]-naphthalene-1 – carboxylic acid amide. A mixture of 4-(4-Formyl-2-methoxy-phenoxy)- naphthalene-1 -carboxylic acid amide (117 mg, 0.36 mmol), thiazolidine-2,4- dione (47.5 mg, 0.36 mmol), sodium acetate (164 mg, 2.0 mmol) and ethanol (3 mL) was heated at reflux overnight. To the mixture was added acetic acid, followed by addition of 3 drops of water, to form a clear solution. This solution was loaded onto a preparative HPLC [Waters XTerra Prep MS C8 OBD Column (5 mum, 30 x 50 mm)] and eluted with a gradient mixture of 0.1 % aqueous TFA and acetonitrile. After triturating with methanol and drying, the pure product was obtained. 1H NMR (400 Hz, DMSO-c/6) ?12.64 (s, 1 H), 8.41 (d, 1 H), 8.21 (d, 1 H), 7.93 (s, 1 H), 7.83 (s, 1 H), 7.65-7.57 (m, 2H), 7.55 (d, 1 H), 7.50 (s, 1 H), 7.48 (s, 1 H), 7.21 (d, 1 H), 7.16 (d, 1 H), 6.68 (d, 1 H), 3.81 (s, 3H); LC/MS (m/z) [M+1]+ 421.0 (calculated for C22Hi7N2O5S, 421.1 ).;

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/109727; (2008); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Analyzing the synthesis route of 2346-26-1

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

WORKING EXAMPLE 12 In substantially the same manner as in Working Example 11, 4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]-3-methoxycinnamaldehyde was condensed with 2,4-oxazolidinedione. The condensate was subjected to catalytic hydrogenation to yield 5-[3-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]-3-methoxyphenyl]propyl]-2,4-oxazolidinedione. The product was recrystallized from chloroform-methanol-ether to give colorless prisms, m.p.173-174 C.

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

New learning discoveries about 2346-26-1

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

A solution of 1.0 g (4.20 mmol) of 2-[4-(1H-pyrrolo[2,3-b]pyridin-1-yl)phenyl]ethanol, prepared in step 13.1., 0.51 g (5.04 mmol) of 1,3-oxazolidine-2,4-dione and 1.21 g (4.62 mmol) of triphenylphosphine in 16 ml of tetrahydrofuran, cooled by a bath of acetone and ice, is admixed dropwise with 0.84 g (4.2 mmol) of diisopropyl azodicarboxylate in solution in 2 ml of tetrahydrofuran. The mixture is subsequently heated to ambient temperature again and stirred overnight. 4 g of silica are added and the mixture is evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 70/30 then 60/40 then 50/50 and 40/60 mixture of cyclohexane and ethyl acetate, to give 1.52 g of product in the form of a sticky solid, which is used as it is in the following step

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

Reference£º
Patent; Sanofi-Aventis; US2006/14830; (2006); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Some tips on 2346-26-1

2346-26-1 Oxazolidine-2,4-dione 97389, aoxazolidine compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

WORKING EXAMPLE 22 In substantially the same manner as in Working Example 11, 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolyl methoxy)cinnamaldehyde was condensed with 2,4-oxazolidinedione. The condensate was subjected to catalytic reduction to yield 5-[3-[3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propyl]-2,4-oxazolidinedione, which was recrystallized from dichloromethane-methanol to give colorless prisms, m.p.180-181 C.

2346-26-1 Oxazolidine-2,4-dione 97389, aoxazolidine compound, is more and more widely used in various.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Downstream synthetic route of 2346-26-1

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a rapidly stirred solution of lithium chloride (510 mg, 12.030 mmol, 3.00 equiv.) and oxazolidine-2,4-dione (380 mg, 3.760 mmol, 1.00 equiv.) in THF (8 mL) under N2 atmosphere at -78 C. was added t-BuLi (7.5 mL, 12.00 mmol, 3.00 equiv) dropwise. The reaction mixture was stirred at -78 C. for 20 minutes then warmed up to 0 C. for 5 minutes. The mixture was recooled to -78 C. and a solution of 2-(6-(8-fluoronaphthalen-2-yl)-2-methoxypyridin-3-yl)-3-methylbutanal (400 mg, 1.186 mmol, 0.30 equiv.) in THF (4 mL) was added. The reaction was stirred at -78 C. for 30 minutes. The reaction was monitored by TLC. Saturated aq. NH4Cl was added and the mixture was extracted with EtOAc, and the combined organic layer. The organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH=20:1) to yield 5-(2-(6-(8-fluoronaphthalen-2-yl)-2-methoxypyridin-3-yl)-1-hydroxy-3-methylbutyl)oxazolidine-2,4-dione as a white solid. Mass spectrum (ESI, m/z): Calculated for C24H23FN2O5, 439.2 (M+H), found 439.1.

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Simple exploration of 2346-26-1

2346-26-1 Oxazolidine-2,4-dione 97389, aoxazolidine compound, is more and more widely used in various.

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

C. 3-Triphenylmethyl-2,4-oxazolidinedione To a solution of 600 mg of 2,4-oxazolidinedione and 601 mg of triethylamine in 7.0 ml of chloroform was added 1.66 g of triphenyl chloromethane and the reaction mixture stirred at room temperature for 30 minutes. The resulting mixture was dissolved in 250 ml of ethyl acetate and washed with water (3*50 ml) and brine (2*20 ml) and dried over sodium sulfate. Removal of the solvent gave 1.8 g of the desired product.

2346-26-1 Oxazolidine-2,4-dione 97389, aoxazolidine compound, is more and more widely used in various.

Reference£º
Patent; Pfizer Inc.; US5498621; (1996); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Brief introduction of 2346-26-1

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

WORKING EXAMPLE 16 In substantially the same manner as in Working Example 11, 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-propoxycinnamaldehyde was condensed with 2,4-oxazolidinedione. The condensate was subjected to catalytic hydrogenation to yield 5-[3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-propoxyphenyl]propyl]-2,4-oxazolidinedione, which was recrystallized from ethyl acetate-ether to give colorless needles, m.p.119-120 C.

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Downstream synthetic route of 2346-26-1

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

WORKING EXAMPLE 18 A mixture of 2-[5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]pentyl]-1,3-dioxolan (3.6 g), 2,4-oxazolidinedione (1.7 g), piperidine (0.72 g) and acetic acid (50 ml) was stirred for 16 hours under reflux. The reaction mixture was concentrated under reduced pressure, which was dissolved in ethyl acetate. The solution was successively washed with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N HCl and water, followed by drying (MgSO4). The ethyl acetate layer was concentrated under reduced pressure, which was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), was obtained 5-[6-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexylidene]-2,4-oxazolidinedione as an oily product. The oily product was dissolved in tetrahydrofuran (THF) (80 ml), to which was added palladium-carbon (5%, 1.0 g). The mixture was subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), was obtained 5-[6-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexyl]-2,4-oxazolidinedione, which was recrystallized from ethyl acetate-isopropyl ether to give colorless prisms, m.p.113-117 C.

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Downstream synthetic route of 2346-26-1

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 100 mL three neck round-bottom flask, were placed oxazolidine-2,4-dione (515 mg, 5.096 mmol, 1 equiv.), LiCl (648 mg, 15.3 mmol, 3 equiv.) and THF (30 mL). The reaction was purged with an inert atmosphere of nitrogen. The mixture was then added t-BuLi (9.6 mL, 15.3 mmol, 1.6M) dropwise with stirring at -78 C. The resulting solution was stirred for 30 min at -78. 1-(6-(8-Fluoronaphthalen-2-yl)-2-methoxypyridin-3-yl)-2-methylpropan-1-one (500 mg, 1.546 mmol, 0.3 equiv.)/THF (3 mL) was added to above solution at -78 C. The resulting solution was stirred for 30 min at -78 C. and 1 hrs at room temperature. The reaction progress was monitored by TLC/LCMS (DCM/MeOH=20:1). The reaction was then quenched by the addition of 3 mL of NH4Cl (aquous). The reaction was extracted with ethyl acetate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (5:95) to yield 5-(1-(6-(8-fluoronaphthalen-2-yl)-2-methoxypyridin-3-yl)-1-hydroxy-2-methylpropyl)oxazolidine-2,4-dione as a white solid. Mass spectrum (ESI, m/z): Calculated for C23H21FN2O5, 425.1 (M+H), found 425.1.

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (181 pag.)US2019/47961; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

Brief introduction of 2346-26-1

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 1.0 g (4.02 mmol) of 2-(4-[(4-chlorophenyl)oxy]phenyl)ethanol, prepared in accordance with Example 14.1., and 1.1 ml (7.89 mmol) of triethylamine in 12 ml of dichloromethane, cooled by an ice bath, is admixed with a solution of 0.60 g (5.24 mmol) of methanesulphonyl chloride in 2 ml of dichloromethane. The combined solutions are subsequently stirred at ambient temperature for 2 hours. They are diluted with 25 ml of water and 75 ml of dichloromethane. After the phases have settled and been separated, the organic phase is washed with 25 ml of water then 25 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness, to give 1.32 g of product in the form of an oil. The product is redissolved in 12 ml of tetrahydrofuran. 0.50 g (5 mmol) of 1,3-oxazolidine-2,4-dione and a solution of 0.92 g (8.0 mmol) of 1,1,3,3-tetramethylguanidine in solution in 4 ml of tetrahydrofuran are added. The mixture is subsequently heated at reflux overnight. It is cooled with an ice bath and 25 ml of an aqueous 0.1N solution of hydrochloric acid and 100 ml of ethyl acetate are added. After the phases have settled, the organic phase is separated off and washed with two times 25 ml of water then with 25 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with an 85/15 then 75/25 and 65/35 mixture of cyclohexane and ethyl acetate, to give 1.20 g of product in the form of a white solid. Melting point ( C.): 105-107

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sanofi-Aventis; US2006/14830; (2006); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem