Category: 875444-08-9

875444-08-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

N-Chlorosuccinimide (10.4 g, 78.1 mmol) was added to a stirred solution of acetaldoxine (3.55 g, 60.1 mrnol) in dry DMF at 00C under N2. The reaction was allowed to warm to room temperature and was stirred for 3 h. Water (100 rnL) was added and the mixture was extracted with Et2O (4 x 80 rnL). The combined extracts were washed with water (50 rnL) and brine (50 mL), dried (Na2SO4) and concentrated in vacuo to afford N-hydroxyethanimidoyl chloride, as a colorless oil. 1H NuMR (500 MHz, CDCl3): delta 8.96 (br s, IH), 2.26 (s, 3 H).Triethylamine (123.4 mg, 170 muL, 1.21 mmol) was added to a stirred solution of (4,S,5.R)-5-[3,5- bis(trifluoromethyl)phenyl]-3-[3-(4-fluoro-5-isopropyl-2-methoxyphenyl)prop-2-yn-l-yl]-4-methyl-l,3- oxazolidin-2-one (21.9 mg, 0.0423 mmol) and N-hydroxyethanimidoyl chloride (124.4 mg, 1.33 mmol) in dry toluene (2 mL) at room temperature under N2. The reaction was heated at reflux for 2 days. The reaction mixture was cooled to room temperature, diluted with IN HCl and extracted with EtOAc (3 x 20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12 x 160 mm, 0-30% EtOAc in hexanes gradient) to afford (45,5Lambda)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3- methylisoxazol-4-yl]methyl}-4-methyl-l,3-oxazolidin-2-one. ^= 0.38 (20% EtOAc/hexanes). LCMS calc. = 575.2; found = 575.3 (M+l)+. 1H NMR (600 MHz, CDCl3): delta 7.84 (s, 1 H); 7.64 (s, 2 H); 7.31 (d, J= 8.3 Hz, 1 H); 6.68 (d, J= 11.8 Hz, 1 H); 5.27 (d, J= 8.0 Hz, 1 H); 4.78 (d, J= 15.6 Hz, 1 H);4.00 (d, J= 15.6 Hz, 1 H); 3.82 (s, 3 H); 3.72-3.68 (m, 1 H); 3.22-3.16 (m, 1 H); 2.38 (s, 3 H); 1.24 (d, J= 7.0 Hz, 3 H); 1.22 (d, J = 7.0 Hz, 3 H); 0.42 (d, J= 6.6 Hz, 3 H).

875444-08-9 (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one 23583229, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK & CO., INC.; WO2007/81569; (2007); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

875444-08-9, (45,5R)-5-[3,5-Z?w(trifluoromethyl)phenyl]-4-methyl-l,3-oxazolidin-2-one (400 mg, 1.28 mrnol) was treated with NaH (60% in oil, 128 mg, 3.2 mmol) and 2-(bromomethyl)-l-iodo-4- (trifluoromethyl)benzene (Example 70, 466 mg, 1,28 mmol) as described in Example 66 to afford (45,5i.)-5-[3,5-Akappa(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-l,3- oxazolidin-2-one as a white solid. LCMS = 598.0 (M+l)+. lH NMR (CDCI3, 500 MHz): delta 8.06 (d, J=8.2 Hz, 1 H), 7.93 (s, 1 H), 7.82 (s, 2 H), 7.61 (s, 1 H), 7.33 (dd, J= 8.2, 1.4 Hz, 1 H), 5.79 (d, J= 7.8 hz, 1 H), 4.91 (d, J= 16 Hz, 1 H), 4.40 (d, J= 16 Hz, 1 H), 4.16-4.06 (m, 1 H), 0.83 (d, J= 6.4 Hz, 3 H).

The synthetic route of 875444-08-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

875444-08-9, iNTERMEDIATE 29 (4S,5R?)-5- 13 ,5-Bis(trifluoromethyl)phenyl] -3- F(5-bromo-2-chloropyridin-4-yl)methyll -4-methyl- 1 ,3-oxazolidin-2-oneA solution of (4S,5R)-5- [3 ,5-bis(trifluoromethyl)phenyl] -4-methyl- 1,3 -oxazolidin-2-one(INTERMEDIATE 4, 1.305 g, 4.17 mmol) in 30 mL of DMF was cooled to -20C. NaHMDS(1.0 M, 4.17 ml, 4.17 mmol) was added and the reaction was stirrred at -20C for 20 minutes.Next, a solution of (5-bromo-2-chloropyridin-4-yl)methyl methanesulfonate (II?1TERMEDIATE28, 1.2522 g, 4.17 mmol) in 5 mL of DMF was added and the solution turned brown. Thereaction was warmed to 0C by switching to an ice/water bath and the reaction stirred for an additional 30 minutes, at which time an LCMS aliquot confirmed the reaction was complete. It was quenched with aqueous NaHCO3. The reaction was extracted with ethyl acetate, then washed with aqueous NaHCO3 and brine, dried with Na2SO4, filtered and the filtrate was concentrated. The crude oil was purified by silica gel chromatography to give the titledcompound as an off-white solid. ?H NMR (CDC13, 500 MHz): 8.52 (s, 1H), 7.92 (s, 1H), 7.80 (s, 2H), 7.36 (s, 1H), 5.81 (d, 1H), 4.78 (d, 1H), 4.34 (d, 1H), 4.17 (m, 1H), 0.82 (d, 3H).

875444-08-9 (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one 23583229, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ACTON, John, J., III; YE, Feng; VACHAL, Petr; SHA, Deyou; DROPINSKI, James, F.; CHU, Lin; ONDEYKA, Debra; KIM, Alexander, J.; COLANDREA, Vincent, J.; ZANG, Yi; ZHANG, Fengqi; DONG, Guizhen; WO2013/165854; (2013); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

The chiral intermediate (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one (compound 11 in Scheme 3, prepared by procedure of WO 2007/005572) (28.0 g) is dissolved in DMF (300 mL) and cooled to – 15C. 2 M NaHMDS (39.2 mL, 1 .05 eq) was then added over 1 h, followed by addition of the biaryl chloride 7 (Scheme 3 ) (28.0 g) in DMF (50 mL), maintaining the internal temperature below -10 C. The mixture was warmed to + 12 C and was aged until complete conversion took place. Then 5M HCI (35 mL) was added, followed by 160 mL of 10% IPAC/Heptanes and 340 mL of water, keeping the temperature between 10C and 20C throughout. The layers were cut and the organic layer was washed twice with 150 mL of 1/1 DMF/water followed by two 140 mL water washes. The organic layerwas then removed under reduced pressure and the resulting residue was purified by flash chromatography (EtOAc/hexanes) to remove the excess oxazolidinone 11 (Scheme 3). The obtained colorless oil was then dissolved in refluxing heptanes (200 mL) and the solution was slowly cooled to -20 C. The resulting slurry was then stirred at -20 C for 2 hours and filtered. The filter cake was washed with cold heptanes and was then dried, yielding 44.0 g (88%) of the desired product of Formula IX (anacetrapib) as an amorphous material. The impurity (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5l-ethyl-4l-fluoro-2′-methoxy-4-(trifluoromethyl) biphenyl-2-yl)methyl)-4-methyloxazolidin-2-one (DMAP) (-3%), which is formed from 2′-(chloromethyl)-5-ethyl-4- fluoro-2-methoxy-4′-(trifluoromethyl)biphenyl (EBFCI) present in the starting material under the conditions described in Step 7, was detected in the product.

As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.

Reference£º
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,875444-08-9

Oxazolidinone III (9.58 g, 30.6 mmol), biaryl chloride II (10.83 g, 30.0 mmol), tetrabutylammonium iodide (0.02 molar equivalents, based on the amount of biaryl chloride), K2CO3 (2 equivalents), and DMF (12 mL) were charged to a 100 mL flask, and the resulting slurry was stirred at 60 C. for 17 hours. Then n-heptane and water were added at the same temperature. The aqueous layer was removed, and the organic layer was washed with water. The product was crystallized by cooling the organic mixture. Isolated crystals were washed with heptane and dried to afford 17.60 g of the titled compound (27.6 mmol, 92%).

As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.

Reference£º
Patent; Chung, Cheol K.; Humphey, Guy R.; Maligres, Peter E.; Wright, Timothy J.; US2014/303380; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

875444-08-9, The chiral intermediate (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one (compound 11 in Scheme 3, prepared by procedure of WO 2007/005572) (28.0 g) is dissolved in DMF (300 mL) and cooled to – 15C. 2 M NaHMDS (39.2 mL, 1.05 eq) was then added over 1 h, followed by addition of the biaryl chloride 7 (Scheme 3) (28.0 g) in DMF (50 mL), maintaining the internal temperature below -10 C. The mixture was warmed to + 12 C and was aged until complete conversion took place. Then 5M HCl (35 mL) was added, followed by 160 mL of 10% IPAC/Heptanes and 340 mL of water, keeping the temperature between 10C and 20C throughout. The layers were cut and the organic layer was washed twice with 150 mL of 1/1 DMF/water followed by two 140 mL waterwashes. The organic layer was then removed under reduced pressure and the resulting residue was purified by flash chromatography (EtOAc/hexanes) to remove the excess oxazolidinone 11 (Scheme 3). The obtained colorless oil was then dissolved in refluxing heptanes (200 mL) and the solution was slowly cooled to -20 C. The resulting slurry was then stirred at -20 C for 2 hours and filtered. The filter cake was washed with cold heptanes and was then dried, yielding 44.0 g (88%) of the desired product of Formula IX (anacetrapib) as an amorphous material. The impurity (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5′-ethyl-4′-fluoro-2′-methoxy-4-(trifluoromethyl) biphenyl-2-yl)methyl)-4-methyloxazolidin-2-one (DMAP) (?3%), which is formed from 2′-(chloromethyl)-5-ethyl-4-fluoro-2-methoxy-4′-(trifluoromethyl)biphenyl (EBFCI) present in the starting material under the conditions described in Step 7, was detected in the product.

875444-08-9 (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one 23583229, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; LEK Pharmaceuticals d.d.; EP2468735; (2012); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

875444-08-9, [2-{[2-(t-butyldimethylsiloxy)ethyl](tetrahydro-2H-pyran-4-yl)amino}-5- (trifIuorornethyl)pyridin-3-yl]methyl methanesulfonate of step 2 and (4S,5f?)-5-[3,5- bis(trifluoromethyl)phenyl])-4-methyl-oxazolidin-2-one were used in the same manner as in step 4 of Example 3 to afford the title compound (55mg, 63%). 1H NMR (400MHz, CDCI3) 8.46 (s, 1H), 7.88 (s, 1 H), 7.77 (s, 1H), 7.73 (s, 2H), 5.72 (d, J = 8.0Hz, 1H), 4.75 (d, J = 16.0Hz, 1 H), 4.33 (d, J = 16.0Hz, 1H), 4.04-3.87 (m, 3H), 3.67 (m, 1 H), 3.50 (m, 2H), 3.38-3.17 (m, 6H), 1.91-1.72 (m, 4H), 0.78 (s, 9H), 0.61 (d, 3H), -0.03 (d, 3H).

As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.

Reference£º
Patent; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9,875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of (45,5J?)-5-[3;5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (12.00 g, 38.3 mmol) in THF (200 mL) was cooled to 0 C. NaH (0.919 g, 38.3 mmol) was added. The mixture was stirred at 0 C for 30 min. The title compound from Step A (10.0 g, 31.9 mmol) in THF (30 mL) was added. The mixture was stirred at 0 C and then room temperature for 4 h. Saturated NH C1 (10 mL) was added. The mixture was extracted with ethyl acetate (3 xlOO mL). The combined organic fractions were washed with brine (saturated, 20 mL), dried (Na2S0 ), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 65i, eluting with EtOAc/hexane (20/80) to give the title compound as a colorless solid. NMR (CDCl3s 500 MHz) delta 8.57 (s, 1H), 7.94 (s, 1H), 7.82 (s, 2H), 5.86 (d, J= 8.5 Hz, 1H), 4.97 (d, J- 18.0 Hz, 1H), 4.46 (m5 1H), 4.28 (d, J= 17.5 Hz, 1H), 2.60 (s, 3H), 0.83 (d, J= 6.5 Hz 3H)

As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LU, Zhijian; CHEN, Yi-Heng; SMITH, Cameron; LI, Hong; THOMPSON, Christopher, F.; SWEIS, Ramzi; SINCLAIR, Peter; KALLASHI, Florida; HUNT, Julianne; ADAMSON, Samantha, E.; DONG, Guizhen; ONDEYKA, Debra, L.; QIAN, Xiaoxia; SUN, Wanying; VACHAL, Petr; ZHAO, Kake; WO2012/58187; (2012); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9,875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The chiral intermediate (4S,5R)-5-[3 ,5-Bis(trifluoromethyl)rhohenyl]-4-methyl-l ,3- oxazolidin-2-one (11) which was made above is dissolved in DMF (2.8 kg in 32.7 L) and cooled to -15 C. 2.0 M NaHMDS (3.92 L, 1.05eq) was then added over 1.5 hr, followed by addition of the biaryl chloride 7 (2.8kg) in DMF. The mixture was warmed to +12C and was aged until complete conversion took place. Then 5N HCl (3.4L) was added, followed by 16L of 10%IPAC/Heptane and 34L of water, keeping the temperature between 100C and 200C throughout. The layers were cut and the organic layer was washed twice with 14L of 1:1 DMF:water followed by two 14L water washes. The organic layer was assayed for yield and was then filtered through 2.4 kg of silica gel to remove the excess oxazolidinone to <0.5%. The silica was washed with 5% IPAC/Heptane. The combined organic solutions were distilled to remove IPAC to <1%. The warm heptane solution was then transferred slowly into a 200C heptane solution containing 10 wt% seed. The slurry was then cooled to -200C and filtered. The filter cake was washed with cold heptane and was then dried, yielding the desired product 12. The synthetic route of 875444-08-9 has been constantly updated, and we look forward to future research findings. Reference£º
Patent; MERCK & CO., INC.; WO2007/92642; (2007); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.,875444-08-9

The chiral intermediate (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one (compound of formula XV; cf. also compound 11 in Scheme 3) (280 mg) prepared by procedure of WO 2007/005572 is dissolved in DMF (30 mL) and cooled to -15C. 2 M NaHMDS (3.90 mL, 1.05 eq) was then added over 1 h, followed by addition of the biaryl chloride EBFCI (270 mg) in DMF (5 mL), maintaining the internal temperature below-10 C. The mixture was warmed to +12 C and was aged until complete conversion took place. Then 5M HCl (3.5 mL) was added, followed by 20 mL of 10% IPAC/Heptanes and 40 mL of water, keeping the temperature between 10C and 20C throughout. The layers were cut and the organic layer was washed twice with 20 mL of 1/1 DMF/water followed by two 15 mL water washes. The organic layer was then removed under reduced pressure and the resulting residue was purified by flash chromatography (EtOActhexanes) to remove the excess oxazolidinone (compound of formula XV). The pure (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5′-ethyl-4′-fluoro-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methyl)-4-methyloxazolidin-2-one (DMAP, compound of formula XII”) was obtained as a colorless oil (388 mg, 80%).

The synthetic route of 875444-08-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LEK Pharmaceuticals d.d.; EP2468736; (2012); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem