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875446-37-0

Basic Information
CAS No.: 875446-37-0
Name: Anacetrapib
Article Data: 17
Molecular Structure:
Molecular Structure of 875446-37-0 (Anacetrapib)
Formula: C30H25F10NO3
Molecular Weight: 637.517
Synonyms: (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-[[4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl]-4-methyl-1,3-oxazolidin-2-one
EINECS: 1312995-182-4
Density: 1.345 g/cm3
Boiling Point: 555.309 °C at 760 mmHg
Flash Point: 289.641 °C
PSA: 38.77000
LogP: 9.70100
Synthetic route

2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl

875444-08-9

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

875446-37-0

anacetrapib

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 17h;92%
Stage #1: (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one With sodium hexamethyldisilazane In N,N-dimethyl-formamide at -15℃; for 1h;
Stage #2: 2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl In N,N-dimethyl-formamide at -15 - 12℃;
88%
Stage #1: (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one With sodium hexamethyldisilazane In N,N-dimethyl-formamide at -15℃; for 1h;
Stage #2: 2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl In N,N-dimethyl-formamide at -10 - 12℃;
88%

C37H33F10NO4

875446-37-0

anacetrapib

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; methanol at 20℃; Inert atmosphere;89%

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl

875446-37-0

anacetrapib

Conditions
ConditionsYield
Stage #1: (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one With sodium hexamethyldisilazane In N,N-dimethyl-formamide at -15℃; for 1.5h;
Stage #2: 2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl In N,N-dimethyl-formamide at -15 - 12℃;
88%
875444-08-9

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

875548-97-3

(4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)methanol

875446-37-0

anacetrapib

Conditions
ConditionsYield
Stage #1: [4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)-1,1'-biphenyl-2-yl]methanol With thionyl chloride In dichloromethane at 5 - 20℃;
Stage #2: (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one With tetra-(n-butyl)ammonium iodide; potassium carbonate In dichloromethane at 60℃;
72%
875446-35-8

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

875446-29-0

[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]boronic acid

875446-37-0

anacetrapib

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; benzene at 100℃; for 14h; Heating / reflux;
With potassium carbonate; palladium diacetate In water; acetone for 1h; Heating / reflux;

C34H29F10NO8(2-)*2Na(1+)

875446-37-0

anacetrapib

Conditions
ConditionsYield
In water-d2 at 37℃; for 3.75h; pH=7.52; Sodium phosphate buffer;
886496-63-5

1-bromo-2-(bromomethyl)-4-(trifluoromethyl)benzene

875444-08-9

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

875446-37-0

anacetrapib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 0 °C
1.2: 0 - 20 °C
2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; water; toluene / Reflux
View Scheme
875446-29-0

[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]boronic acid

1185737-50-1

(4S,5R)-5-(3,5-bis-trifluoromethyl-phenyl)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-oxazolidin-2-one

875446-37-0

anacetrapib

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Suzuki coupling; Reflux;
74457-86-6

1-(2-fluoro-4-methoxyphenyl)-1-ethanone

875446-37-0

anacetrapib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / 1 h / -15 - 0 °C
2.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr
3.1: N-Bromosuccinimide / acetonitrile / 35 °C
4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 24 h / 35 °C / Inert atmosphere
6.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C
7.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C
7.2: -15 - 12 °C
View Scheme
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / 1 h / -15 - 0 °C
2.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr
3.1: N-Bromosuccinimide / acetonitrile / 35 °C
4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 30 - 45 °C / Inert atmosphere
6.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C
7.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C
7.2: -15 - 12 °C
View Scheme
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / 1 h / -15 - 0 °C
2.1: N-Bromosuccinimide / acetonitrile / 60 °C
3.1: trifluoroacetic acid; 1,1,3,3-Tetramethyldisiloxane / 1,2-dichloro-ethane / 0.25 h / -20 - -10 °C
4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere
4.2: 1 h / 15 - 20 °C / pH 2
5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 °C / Inert atmosphere
6.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 10 - 20 °C
7.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C
7.2: -10 - 12 °C
View Scheme
96826-25-4

2-(2-fluoro-4-methoxyphenyl)-2-isopropanol

875446-37-0

anacetrapib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr
2.1: N-Bromosuccinimide / acetonitrile / 35 °C
3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 24 h / 35 °C / Inert atmosphere
5.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C
6.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C
6.2: -15 - 12 °C
View Scheme
Multi-step reaction with 6 steps
1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr
2.1: N-Bromosuccinimide / acetonitrile / 35 °C
3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 30 - 45 °C / Inert atmosphere
5.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C
6.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C
6.2: -15 - 12 °C
View Scheme
Multi-step reaction with 6 steps
1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr
2.1: N-Bromosuccinimide / acetonitrile / 35 °C
3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere
3.2: 1 h / 15 - 20 °C / pH 2
4.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 °C / Inert atmosphere
5.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 10 - 20 °C
6.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C
6.2: -10 - 12 °C
View Scheme
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    Product Name: Anacetrapib Synonyms: Anacetrapib;Mk0859;Mk-0859;Unii-p7T269pr6s;(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-[[4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphen

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Specification

The MK-0859 is an organic compound with the formula C30H25F10NO3. The IUPAC name of this chemical is (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[[2-(4-fluoro-2-methoxy-5-propan-2-ylphenyl)-5-(trifluoromethyl)phenyl]methyl]-4-methyl-1,3-oxazolidin-2-one. With the CAS registry number 875446-37-0, it is also named as Mk-0859.

Physical properties about MK-0859 are: (1)ACD/LogP: 7.28; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 9; (4)ACD/LogD (pH 7.4): 9; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 1475720; (8)ACD/KOC (pH 7.4): 1475720; (9)#H bond acceptors: 4; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 38.77 Å2; (12)Index of Refraction: 1.494; (13)Molar Refractivity: 137.845 cm3; (14)Molar Volume: 473.897 cm3; (15)Polarizability: 54.646×10-24cm3; (16)Surface Tension: 33.07 dyne/cm; (17)Density: 1.345 g/cm3; (18)Flash Point: 289.641 °C; (19)Enthalpy of Vaporization: 83.659 kJ/mol; (20)Boiling Point: 555.309 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2O[C@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)[C@@H](N2Cc4c(c3cc(c(F)cc3OC)C(C)C)ccc(c4)C(F)(F)F)C
(2)InChI: InChI=1/C30H25F10NO3/c1-14(2)22-11-23(25(43-4)12-24(22)31)21-6-5-18(28(32,33)34)9-17(21)13-41-15(3)26(44-27(41)42)16-7-19(29(35,36)37)10-20(8-16)30(38,39)40/h5-12,14-15,26H,13H2,1-4H3/t15-,26-/m0/s1
(3)InChIKey: MZZLGJHLQGUVPN-HAWMADMCBN
(4)Std. InChI: InChI=1S/C30H25F10NO3/c1-14(2)22-11-23(25(43-4)12-24(22)31)21-6-5-18(28(32,33)34)9-17(21)13-41-15(3)26(44-27(41)42)16-7-19(29(35,36)37)10-20(8-16)30(38,39)40/h5-12,14-15,26H,13H2,1-4H3/t15-,26-/m0/s1
(5)Std. InChIKey: MZZLGJHLQGUVPN-HAWMADMCSA-N