Category: 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

875444-08-9, 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, (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

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl-4- methyloxazolidin-2-one (46g, 147mol) in DMF (150ml) was dropwise added NaHMDS (176ml, 176mol) at -40C. The reaction mixture was stirred for 30 min, and slowly added with drops of a dilution of 5-bromo-3-(chloromethyl)-N-cyclohexyl-N-ethylpyrid’ine-2-amine of step 3 in DMF (30ml). The resulting reaction mixture was heated to room temperature, stirred for 3 hrs, and diluted with ethyl acetate (200ml) before quenching with water (500ml). The organic layer was withdrawn, washed with water (1.5L), and filtered through a silica- selite pad in a vacuum to afford the title compound (60g, 67%). 1H NMR (400 MHz, CDCI3) 8.31 (s, 1 H), 7.89 (s, 1 H), 7.76 (s, 2 H), 7.74 (s, 1 H), 5.73 (d, 1 H, J = 8.0 Hz), 4.68 (d, 1 H, J = 16.0 Hz), 4.30 (d, 1 H, J = 16.0 Hz), 3.93 (m, 1 H), 3.44 (m, 1 H), 3.03 (m, 1 H), 2.68 (m, 1 H), 1.44- .86 (m, 5 H), 1.02-1.44 (m, 5 H), 0.86 (t, 3 H, J = 6.8 Hz), 0.66 (d, 3 H, J = 6.4 Hz).

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

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

To a stirred suspension of sodium hydride (60% dispersion in mineral oil; 1.3 g; 0.0325 mol) in THF (60mL) at 0 C under N2 was added dropwise a solution of (4S,5ft)-5-[3,5-bis(trifluoromethyl)phenyi]-4-methyl-l,3-oxazolidin-2-one (Example 17) (4.077 g; 0.013 mol) in THF (50 mL). Gas evolution wasobserved. The resultant mixture stirred at 0 C for 30 min prior to addition of a solution of 2-(bromomethyl)-l-iodo-4-(trifluoromethyl)benzene (4.754 g; 0.013 mol) in THF (20 mL). The reactionwas allowed to warm to room temperature and stirred for 14 h. The reaction was carefully quenchedwith H2O (15 mL) and partitioned between EtOAc (250 mL) and H2O (75 mL). The aqueous layer wasextracted with EtOAc (3 x 100 mL). Combined organic layers were washed with brine (100 mL), dried(MgSO4), filtered and concentrated in vacua. The residue was purified by flash chromatography (0-20%EtOAc/hexanes gradient) to afford 6.4 g (82.5%) of (4S,5fl)-5-[3,5-bis(trifluoromemyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-l,3-oxazolidin-2-one as a white solid. LCMS = 598.1 (M+l)+.*H NMR (CDC13, 500 MHz): 5 8.03 (d, J = 8.2 Hz, 1 H), 7.90 (s, 1 H), 7.79 (s, 2 H), 7.58 (s, 1H), 7.30(dd, J = 8.2 Hz, J = 2.0 Hz, 1 H), 5.76 (d, J = 8 Hz, 1 H), 4.88 (d, J = 15.8 Hz, 1 H), 4.37 (d, J = 15.8 Hz,1 H), 4.09-4.02 (m, 1 H), 0.8 (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.

Reference£º
Patent; MERCK & CO., INC.; WO2006/14357; (2006); 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

Synthesis of (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((4′-fluoro-5′-(1,1,1,2,3,3,3-d7)isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methyl)-4-methyl-1,3-oxazolidin-2-one (Compound 164). A solution of (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyl-1,3-oxazolidin-2-one (18a) [prepared by methods described in WO2007/005572] (112 mg) in DMF (2 mL) was cooled to -20 C. and 1M NaHMDS in THF (0.4 mL) was added slowly, maintaining the reaction temperature at <-15 C. After 5 min, a solution of 17a (110 mg) in DMF (0.5 mL) was added dropwise at <-15 C. The reaction mixture was allowed to warm slowly to 15-16 C. and stirred for 2 hr. The mixture was diluted with MTBE (50 mL) and the solution washed with water (10 mL*2), dilute HCl solution, brine, dried (Na2SO4), filtered and the solvent removed under reduced pressure. The crude product was purified by chromatography on silica gel to give 10 mg of Compound 164. MS m/z=645 (M+H), 667 (M+Na). 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. Reference£º
Patent; CONCERT PHARMCEUTICALS, INC.; US2008/242711; (2008); 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

A solution of ethyl [trans-4-( {ethyl [2-(hydroxymethyl)-4-(trifluoromethyl)phenyl] amino}methyl)cyclohexyl]acetate (Step B; 60 mg; 0.149 mmol) in toluene (1 mL) was added dropwise to a stirred solution of thionyl chloride (12.3 muL; 0.169 mmol) in toluene (300 muL) at 0C. The reaction stirred at room temperature for 1.5 h. Pyridine (27 mL) was added and the reaction was partitioned between toluene (10 mL) and H2O (10 mL). The aqueous layer was re-extracted with toluene (10 mL) and the combined organic layers were washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in DMF (1 mL) and (45,5i?)-5-[3,5- bis(trifluoromethyl)phenyl]-4-methyl-l,3-oxazolidin-2-one (intermediate 17; 56 mg; 0.179 mmol) and potassium terf-butoxide (23.5 mg; 0.209 mmol) were added successively. The reaction stirred for 72 h and was quenched with sat. NH4Cl. The reaction was partitioned between sat. NH4Cl (10 mL) and EtOAc (10 mL). The aqueous layer was re-extracted with EtOAc (3 x 10 mL) and the combined organic layers were washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-20% EtOAc/hexanes gradient) and chiral HPLC (1.5% IP A/heptane; ChiralPak IA column) to afford ethyl (&r¡ãw-4-{[[2-({(4S,5lambda)-5-[3,5- bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-l,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl](ethyl)amino]methyl}cyclohexyl)acetate as a clear glass. LCMS = 697.3 (M+l)+. IH NMR (CDCl3, 500 MHz): delta 7.92 (s, 1 H), 7.81 (s, 2 H), 7.65 (s, 1 H), 7.58 (d, J = 8.4 Hz, 1 H), 7.30-7.27 (m, 1 H)5 5.78 (d, J= 8.1 Hz3 1 H), 4.88 (d, J= 16.5 Hz, 1 H)5 4.74-4.69 (m, 1 H), 4.11 (q, J= 7.1 Hz, 2 H), 3.17-3.10 (m, 2 H), 3.05-2.97 (m, 2 H), 2.15 (d, J= 6.8 Hz, 2 H), 1.80-1.68 (m, 4 H), 1.66-1.50 (m, 1 H), 1.46-1.39 (m, 1 H), 1.25 (t, J= 7.1 Hz, 3 H), 1.07 (t, J= 7.0 Hz, 3 H), 1.03-0.85 (m, 4 H), 0.71 (d, J= 6.6 Hz, 3 H).

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

Reference£º
Patent; MERCK & CO., INC.; WO2007/81571; (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

3′-(2-(Bromomethyl)-4,4-dicyclohex-l-enyl)-3,5-difiuoro-4′-methoxy-4-(methoxy methoxy)biphenyl, which is an intermediate compound, was dissolved in dimethylformamide (DMF). (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-oxazolidin-2-one and sodium hydride were added dropwise to the obtained solution at room temperature. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate, washed with water and brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was separated by MPLC (Si02, 5:1 n-hexane : EtOAc), thus obtaining Compound 304 (60 mg, 46%) as white oil.1H NMR (400 MHz, DMSO-d6); atropisomer mixture; delta 7.86 (s, 1 H), 7.79 (s, 2 H), 7.36 – 7.39 (m, 1 H), 6.88 – 6.95 (m, 3 H), 5.57 – 5.62 (m, 1 H), 5.17 (d, 1 H, J= 9.9 Hz), 3.96 -4.04 (m, 2 H), 3.79 – 3.82 (2s, 3 H), 3.58 – 3.62 (m, 3 H), 3.44 – 3.58 (m, 1 H), 2.00 – 2.50 (m, 2 H), 1.93 – 1.95 (m, 2 H), 1.50 – 1.55 (m, 2 H), 1.02 – 1.07 (m, 6 H), 0.37, 0.43 (2d, 3 H, J= 6.6,6.5 Hz); MS (ESI) m/z 714 (M+ + H).

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

Reference£º
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Seohee; OH, Jungtaek; LEE, Jaekwang; LEE, Jaewon; BAE, Suyeal; HA, Nina; LEE, Sera; WO2012/141487; (2012); 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

A solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl])-4-methyl-oxazolidin-2-one (1.78g, 5.68mmol), obtained in step 2 of Example 1 , in DMF (10ml) was added with drops of NaHMDS (5.16ml, 5.16mmol) at -40C, and stirred for 30 min. To this mixture was slowly added a solution of 3-(chloromethyl)-N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-5- (trifluoromethyl)pyridine-2-amine, obtained in step 3, in DMF (5ml), after which the reaction mixture was stirred at room temperature for 2 hrs. The reaction was terminated with a saturated aqueous ammonium solution, followed by extraction with ethyl acetate. The residue was purified by chromatography to afford the title compound ( .92g, 64%). H NMR (400MHz, CDCI3) 8.51 (s, 1 H), 7.88 (s, 1H), 7.79 (d, J = 2.0Hz, 1H), 7.77 (s, 2H), 5.72 (d, J = 8.0Hz, 1H), 4.75 (d, J = 16.0Hz, 1 H), 4.34 (d, J = 16.0Hz, 1H), 4.00 (m, 2H), 3.46 (m, 6H), 1.86 (m, 4H), 0.93 (t, 3H), 0.63 (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.

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, (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

Step 5: (4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-bromo-5-tri?uoromethyl-benzyl)-4- niethyl-oxazolidin-2-one[00524] To (4S,5R)-5-(3,5-bis-t?fluoromethyl-phenyl)-4-methyl-oxazohdin-2-one (0246g,0 79mmol) in THF (1OmL) at room temperature was added sodium hexamethyldisilazane (IM inTHF, 1 02mL, 1 02mmol), and the reaction was stirred for 15 minutes 2-Bromo-5-(tnfluoromethyl)benzyl bromide (025Og, 0 79mmol) was added, and the reaction was stirred overnight at room temperature The mixture was worked-up with EtOAc and H2O, and the crude material was purified by silica gel chromatography to give the title compound

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

Reference£º
Patent; AMIRA PHARMACEUTICALS, INC.; WO2009/108720; (2009); 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.

(45,5i?)-5-[3,5-w(trifluoromethyl)phenyl]-4-methyl-l,3-oxazolidin-2-one (Intermediate 17, 400 mg, 1.28 mmol) was treated with NaH (60% in oil, 128 mg, 3.2 mmol) and 2-(bromomethyl)-l-iodo-4- (trifluoromethyl)benzene (Intermediate 11, 466 mg, 1,28 mmol). The reaction was stirred at room temperature for 18 h. The reaction was quenched with H2O (1 mL) and partitioned between EtOAc (80 mL) and H2O (25 mL). The aqueous phase was re-extracted with EtOAc (2 x 20 mL) and the combined organic extracts were washed with brine (30 mL), dried (MgStheta4) and concentrated in vacuo to give the crude product. This was purified by flash silica-gel chromatography (0-30% EtOAc in hexanes gradient) to afford (4S’,5i?)-5-[3,5-/5(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)3 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)54.40 (d, J= 16 Hz, 1 H), 4.16-4.06 (m, 1 H), 0.83 (d, J= 6.4 Hz, 3 H).

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

Reference£º
Patent; MERCK & CO., INC.; WO2007/81571; (2007); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem