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170729-80-3

Basic Information
CAS No.: 170729-80-3
Name: Aprepitant
Molecular Structure:
Molecular Structure of 170729-80-3 (Aprepitant)
Formula: C23H21F7N4O3
Molecular Weight: 534.43
Synonyms: 3H-1,2,4-Triazol-3-one,5-[[2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-,[2R-[2a(R*),3a]]-;Emend;L 754030;MK 0869;MK 869;ONO7436;
EINECS: 677-636-6
Density: 1.51 g/cm3
Melting Point: 75-76°C(lit.)
Boiling Point:
Flash Point:
Solubility:
Appearance: off-white to light yellow cyrstalline solid
Hazard Symbols: Xn,Xi
Risk Codes: R20/21/22; R36/37/38
Safety:
Transport Information:
PSA: 83.24000
LogP: 4.89000
Synthetic route
252742-72-6

3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one

(2R,3S)-2-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine 4-methylbenzenesulfonate

170729-80-3

aprepitant

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide at 0℃; for 3h;99%
219821-37-1

2-[2-[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]-1-iminoethyl]hydrazinecarboxylic acid methyl ester

170729-80-3

aprepitant

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Reflux;98.4%
In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 139℃; for 4h; Temperature;97.7%
In acetonitrile at 120 - 125℃;60.4%

C3H4BrN3O

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine hydrochloride

170729-80-3

aprepitant

Conditions
ConditionsYield
With diethyl sulfate; triethylamine; lithium diisopropyl amide In dimethylsulfoxide-d6; 5,5-dimethyl-1,3-cyclohexadiene at 33℃; for 14h; Temperature; Inert atmosphere;97.9%

C23H21F7N4O4

170729-80-3

aprepitant

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate In acetonitrile at 0 - 35℃; for 5h;94%
252742-72-6

3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine hydrochloride

170729-80-3

aprepitant

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 10℃; for 4h;92%
252742-72-6

3-(chloromethyl)-1H-1,2,4-triazol-5(4H)-one

171338-27-5

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine

170729-80-3

aprepitant

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;68%

N'-(1-amino-2-chloroethylidene)hydrazinecarboxylic acid methyl ester

171338-27-5

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine

170729-80-3

aprepitant

Conditions
ConditionsYield
Stage #1: N'-(1-amino-2-chloroethylidene)hydrazinecarboxylic acid methyl ester; [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h;
Stage #2: In acetonitrile at 110℃; under 1125.11 Torr; for 55h; Product distribution / selectivity;
53%
219821-37-1

2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(S)-4-fluorophenyl-4-2-(N-methylcarboxyactamidrazono)morpholine

170729-80-3

aprepitant

Conditions
ConditionsYield
With pyrographite In methanol at 60℃; for 1h;0.96 kg
In toluene at 140℃; for 3h;
at 135 - 137℃; for 2h;

(2R,3S)-4-benzyl-2-[1R-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine p-toluenesulfonate salt

N-methoxycarbonyl-2-chloroacetamidrazone

170729-80-3

aprepitant

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20 - 23℃; for 1.5h; Product distribution / selectivity;
30071-93-3

3,5-bis(trifluoromethyl)phenyl methyl ketone

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97 percent / borane-methyl sulfide complex; (S)-Me-CBS / various solvent(s); toluene / 1 h / -5 °C
2: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 5 steps
1: 97 percent / borane-methyl sulfide complex; (S)-Me-CBS / various solvent(s); toluene / 1 h / -5 °C
2: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
4: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
5: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: 97 percent / borane-methyl sulfide complex; (S)-Me-CBS / various solvent(s); toluene / 1 h / -5 °C
2: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
368-63-8, 68120-60-5, 127852-28-2

(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 4 steps
1: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
3: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
4: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
110843-90-8

4-benzyl-morpholine-2,3-dione

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / lithium tri(sec-butyl)borohydride; sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 1 h / 10 °C
2: acetonitrile / 5 - 34 °C
3: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
4: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 6 steps
1: 80 percent / lithium tri(sec-butyl)borohydride; sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 1 h / 10 °C
2: acetonitrile / 5 - 34 °C
3: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
4: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
5: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
6: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: 80 percent / lithium tri(sec-butyl)borohydride; sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 1 h / 10 °C
2: 91 percent / DBU / toluene; heptane / 18 h / 20 °C
3: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
4: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
104-63-2

N-Benzylethanolamine

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 76 percent / tetrahydrofuran; H2O / 21 h / Heating
2: acetonitrile / 5 - 34 °C
3: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
4: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 6 steps
1: 76 percent / tetrahydrofuran; H2O / 21 h / Heating
2: acetonitrile / 5 - 34 °C
3: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
4: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
5: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
6: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: 76 percent / tetrahydrofuran; H2O / 21 h / Heating
2: 91 percent / DBU / toluene; heptane / 18 h / 20 °C
3: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
4: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine hydrochloride

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
2: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 10 - 20 °C
2: potassium hydroxide / ethanol; water / 0.2 h / 90 - 100 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 10 - 20 °C
2: potassium hydroxide / ethanol; water / 0.2 h / 90 - 100 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 5,5-dimethyl-1,3-cyclohexadiene; dimethyl sulfoxide / 20 - 25 °C / Inert atmosphere
2: 5,5-dimethyl-1,3-cyclohexadiene / 2 h / 135 - 141 °C / Inert atmosphere
View Scheme
287930-73-8

4-benzyl-2-hydroxy-morpholin-3-one

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetonitrile / 5 - 34 °C
2: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 5 steps
1: acetonitrile / 5 - 34 °C
2: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
4: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
5: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: 91 percent / DBU / toluene; heptane / 18 h / 20 °C
2: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
502537-07-7

trifluoro-acetic acid 4-benzyl-3-oxo-morpholin-2-yl ester

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 4 steps
1: 3.51 kg / BF3*Et2O / acetonitrile / 2 h / 20 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
3: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
4: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
502536-97-2

2,2,2-trichloro-acetimidic acid 4-benzyl-3-oxo-morpholin-2-yl ester

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
2: KO-t-Bu / 2-methyl-propan-2-ol; hexane / 16 h / 22 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 3 steps
1: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 4 steps
1: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
3: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
4: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: boron trifluoride etherate / toluene; heptane / 1 h / 20 °C
2: KO-t-Bu / 2-methyl-propan-2-ol; hexane / 16 h / 22 °C
3: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
4: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
5: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
327623-36-9

(2S,2αR)-4-benzyl-2-[1-[3,5-bis(trifluoromethyl)phenyl]]ethoxy-morpholin-3-one

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: KO-t-Bu / 2-methyl-propan-2-ol; hexane / 16 h / 22 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 4 steps
1: KO-t-Bu / 2-methyl-propan-2-ol; hexane / 16 h / 22 °C
2: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
3: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
4: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
287930-75-0

(2R,2αR)-4-benzyl-2-[1-[3,5-bis(trifluoromethyl)phenyl]]ethoxy-morpholin-3-one

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
View Scheme
Multi-step reaction with 3 steps
1: 47.6 g / 4-toluenesulfonic acid; H2; HCl / Pd/C / tetrahydrofuran; methanol / 3 h / 20 - 25 °C / 1034.32 Torr
2: potassium carbonate / toluene; dimethylsulfoxide / 2 h / 15 °C
3: 0.96 kg / Darco / methanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 5%-palladium/activated carbon; hydrogen / methanol; water / 4.5 h / 50 - 60 °C / 26252.6 Torr
2.1: sodium hydroxide / acetonitrile / 2.5 h / 30 - 40 °C
3.1: tetrahydrofuran / 1 h / 15 - 25 °C
3.2: 1 h / 20 - 65 °C
4.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 5 h / 0 - 35 °C
View Scheme
472968-68-6

(2S,3R)-3-(4-fluorophenyl)-4-[(1R)-1-phenylethyl]-2-morpholinol

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: K2CO3 / toluene / 5 h / 20 °C
2: 14.3 g / BF3*Et2O / tetrahydrofuran / 1 h / -20 °C
3: TsOH*H2O; hydrogen / 5percent Pd/C / ethanol; toluene / 3 h / 30 °C / 2068.65 Torr
4: NCS; K2CO3 / dimethylformamide / 0.5 h / 0 °C
5: DBU / dimethylformamide / 3 h / 0 - 20 °C
6: hydrogen / 5percent Pd/C / dimethylformamide; ethanol / 2 h / 20 °C / 2068.65 Torr
View Scheme

(3R)-[3-(4-fluorophenyl)]-4-[(1R)-1-phenylethyl]-2-morpholinone

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: DIBALH / toluene; tetrahydrofuran / 0.5 h / -20 °C
2: K2CO3 / toluene / 5 h / 20 °C
3: 14.3 g / BF3*Et2O / tetrahydrofuran / 1 h / -20 °C
4: TsOH*H2O; hydrogen / 5percent Pd/C / ethanol; toluene / 3 h / 30 °C / 2068.65 Torr
5: NCS; K2CO3 / dimethylformamide / 0.5 h / 0 °C
6: DBU / dimethylformamide / 3 h / 0 - 20 °C
7: hydrogen / 5percent Pd/C / dimethylformamide; ethanol / 2 h / 20 °C / 2068.65 Torr
View Scheme
472968-69-7

2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 14.3 g / BF3*Et2O / tetrahydrofuran / 1 h / -20 °C
2: TsOH*H2O; hydrogen / 5percent Pd/C / ethanol; toluene / 3 h / 30 °C / 2068.65 Torr
3: NCS; K2CO3 / dimethylformamide / 0.5 h / 0 °C
4: DBU / dimethylformamide / 3 h / 0 - 20 °C
5: hydrogen / 5percent Pd/C / dimethylformamide; ethanol / 2 h / 20 °C / 2068.65 Torr
View Scheme
380499-07-0

(2R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / 5percent Pd/C / dimethylformamide; ethanol / 2 h / 20 °C / 2068.65 Torr
View Scheme
Multi-step reaction with 2 steps
1.1: potassium formate / palladium on carbon / ethanol; water / 2 h / 20 °C
2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C
2.2: 55 h / 110 °C / 1125.11 Torr
View Scheme
380499-06-9

(2R,3R)-2-[(1R)-1-(3,5-bis-trifluoro-methylphenyl)ethoxy]-3-(4-fluorophenyl)morpholine

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NCS; K2CO3 / dimethylformamide / 0.5 h / 0 °C
2: DBU / dimethylformamide / 3 h / 0 - 20 °C
3: hydrogen / 5percent Pd/C / dimethylformamide; ethanol / 2 h / 20 °C / 2068.65 Torr
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hypochlorite; potassium carbonate / acetonitrile / 0.25 h
1.2: 14 h / 20 °C
2.1: potassium formate / palladium on carbon / ethanol; water / 2 h / 20 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hypochlorite; potassium carbonate / acetonitrile / 0.25 h
1.2: 14 h / 20 °C
2.1: potassium formate / palladium on carbon / ethanol; water / 2 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C
3.2: 55 h / 110 °C / 1125.11 Torr
View Scheme

(2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-4-chloro-3-(4-fluoro-phenyl)-morpholine

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: DBU / dimethylformamide / 3 h / 0 - 20 °C
2: hydrogen / 5percent Pd/C / dimethylformamide; ethanol / 2 h / 20 °C / 2068.65 Torr
View Scheme
472968-70-0

(2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholine

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: TsOH*H2O; hydrogen / 5percent Pd/C / ethanol; toluene / 3 h / 30 °C / 2068.65 Torr
2: NCS; K2CO3 / dimethylformamide / 0.5 h / 0 °C
3: DBU / dimethylformamide / 3 h / 0 - 20 °C
4: hydrogen / 5percent Pd/C / dimethylformamide; ethanol / 2 h / 20 °C / 2068.65 Torr
View Scheme
1349902-81-3

C27H31F7N4O4

170729-80-3

aprepitant

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 90 - 100℃; for 1h; Reagent/catalyst; Solvent; Large scale;

C25H27F7N4O4

170729-80-3

aprepitant

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 90 - 100℃; for 0.2h;
1185503-10-9

(2S,3R)-4-benzyl-3-(4-fluorophenyl)morpholin-2-ol

170729-80-3

aprepitant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: boron trifluoride diethyl etherate / toluene / 1 h / -10 °C
2.1: hydrogen; toluene-4-sulfonic acid / palladium 10% on activated carbon / methanol / 16 h / 20 °C
3.1: sodium hypochlorite; potassium carbonate / acetonitrile / 0.25 h
3.2: 14 h / 20 °C
4.1: potassium formate / palladium on carbon / ethanol; water / 2 h / 20 °C
5.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: boron trifluoride diethyl etherate / toluene / 1 h / -10 °C
2.1: hydrogen; toluene-4-sulfonic acid / palladium 10% on activated carbon / methanol / 16 h / 20 °C
3.1: sodium hypochlorite; potassium carbonate / acetonitrile / 0.25 h
3.2: 14 h / 20 °C
4.1: potassium formate / palladium on carbon / ethanol; water / 2 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C
5.2: 55 h / 110 °C / 1125.11 Torr
View Scheme
6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

170729-80-3

aprepitant

Fosaprepitant dimeglumine

Conditions
ConditionsYield
Stage #1: aprepitant With dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate; sodium hexamethyldisilazane In tetrahydrofuran at -3℃; for 2h;
Stage #2: 1-deoxy-1-(methylamino)-D-glucitol With palladium 10% on activated carbon; hydrogen In methanol; water for 4h;
98%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

170729-80-3

aprepitant

265121-01-5

[3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]phosphonic acid bis(phenylmethyl)ester

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Temperature; Inert atmosphere;93.6%
With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Temperature; Inert atmosphere;93.6%
With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.25h; phosphorylation;90%
17176-77-1

Dibenzyl phosphite

170729-80-3

aprepitant

265121-01-5

[3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]phosphonic acid bis(phenylmethyl)ester

Conditions
ConditionsYield
With triethylamine In tetrachloromethane; dichloromethane at 0 - 10℃; Reagent/catalyst; Solvent;92.4%
868-85-9

Dimethyl phosphite

170729-80-3

aprepitant

C25H26F7N4O6P

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tert-butyl methyl ether at 0 - 30℃;90.6%
762-04-9

phosphonic acid diethyl ester

170729-80-3

aprepitant

C27H30F7N4O6P

Conditions
ConditionsYield
With dmap In chloroform at 0 - 20℃;90.4%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

170729-80-3

aprepitant

dibenzyl fosaprepitant

Conditions
ConditionsYield
Stage #1: aprepitant With lithium hydroxide monohydrate In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h;
Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In 1-methyl-pyrrolidin-2-one at 25 - 30℃; for 0.5h; Quantum yield;
87.4%
170729-80-3

aprepitant

fosaprepitant

Conditions
ConditionsYield
With dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate; sodium hexamethyldisilazane In tetrahydrofuran at -3℃; for 2h;86.7%
Multi-step reaction with 3 steps
1: sodium hexamethyldisilazane / tetrahydrofuran / 3.5 h / -20 °C
2: hydrogen / palladium 10% on activated carbon / methanol / 1 h / 5171.62 Torr
3: hydrogenchloride / water; methanol / 0.08 h / 0 - 5 °C / pH 1
View Scheme
Multi-step reaction with 2 steps
1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2: borane pyridine; methanol / 2 h / 20 °C / Inert atmosphere
View Scheme

C26H22ClO3P

170729-80-3

aprepitant

C49H42F7N4O6P

Conditions
ConditionsYield
Stage #1: aprepitant With sodium hexamethyldisilazane In tetrahydrofuran at -5 - 5℃; for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: C26H22ClO3P In tetrahydrofuran at 5 - 20℃; for 1h; Solvent;
82%
53148-24-6

benzyl methyl phosphonate

170729-80-3

aprepitant

C31H30F7N4O6P

Conditions
ConditionsYield
With triethylamine In tetrachloromethane; dichloromethane at 0 - 10℃; Reagent/catalyst; Solvent;81.1%
170729-80-3

aprepitant

5-(((2R,3S)-2-((R)-1-(3-(difluoromethyl-d)-5-(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions
ConditionsYield
With deuteroacetic acid; magnesium In dimethylsulfoxide-d6; d(4)-methanol; water-d2 at 20℃; for 2h; regioselective reaction;43%
170729-80-3

aprepitant

5-(((2R,3S)-2-((R)-1-(3-(difluoromethyl)-5-(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions
ConditionsYield
With magnesium; acetic acid In water; dimethyl sulfoxide at 20℃; for 2h; regioselective reaction;41%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

170729-80-3

aprepitant

A

265121-01-5

[3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]phosphonic acid bis(phenylmethyl)ester

B

C44H41F7N4O9P2

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.75h; phosphorylation;A 39%
B 5 % Chromat.
170729-80-3

aprepitant

A

5-(((2R,3S)-2-((R)-1-(3-(fluoromethyl)-5-(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

B

5-(((2R,3S)-2-((R)-1-(3-(difluoromethyl)-5-(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions
ConditionsYield
With magnesium; acetic acid In water; dimethyl sulfoxide at 20℃; for 5h; regioselective reaction;A 16%
B 22%
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Chemistry

Product Name: Aprepitant (CAS NO.170729-80-3)

Molecular Formula: C23H21F7N4O3
Molecular Weight: 534.43g/mol
Mol File: 170729-80-3.mol
Appearance: Off-White to Light Yellow Cyrstalline Solid
Density: 1.51 g/cm3
Index of Refraction: 1.564 
Molar Refractivity: 115.07 cm3 
Molar Volume: 353.5 cm
Surface Tension: 39 dyne/cm
XLogP3-AA: 4.2
H-Bond Donor: 2
H-Bond Acceptor: 12
Structure Descriptors of Aprepitant (CAS NO.170729-80-3):
  IUPAC Name: 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one 
  Canonical SMILES: CC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OC2C(N(CCO2)CC3=NC(=O)NN3)C4=CC=C(C=
C4)F
  Isomeric SMILES: C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](N(CCO2)CC3=NC(=O)
NN3)C4=CC=C(C=C4)F
  InChI: InChI=1S/C23H21F7N4O3/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)37-20-19(13-2-4-17(24)5-3-13)34(6-7-36-20)11-18-31-21(35)33-32-18/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H2,31,32,33,35)/t12-,19+,20-/m1/s1 
  InChIKey: ATALOFNDEOCMKK-OITMNORJSA-N
Product Categories: Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals

Uses

 Aprepitant (CAS NO.170729-80-3) is classified as an NK1 antagonist.  Aprepitant(170729-80-3) also has been shown to inhibit both the acute and delayed emesis induced by cytotoxic chemotherapeutic.

Toxicity Data With Reference

 Aprepitant (CAS NO.170729-80-3)  should not be used concurrently with pimozide, terfenadine, astemizole, or cisapride. Dose-dependent inhibition of CYP3A4 by Aprepitant could result in elevated plasma concentrations of these drugs, potentially causing serious or life-threatening reactions.

Specification

 Aprepitant , its CAS NO. is 170729-80-3, the synonyms are 3-(((2R,3S)-3-(p-Fluorophenyl)-2-(((alphaR)-alpha-methyl-
3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-delta(sup 2)-1,2,4-triazolin-5-one ; 3H-1,2,4-Triazol-3-one, 5-(((2R,3S)-2-((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)-4-morpholinyl)methyl)-1,2-dihydro- ; Emend .