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170729-80-3

Basic Information
CAS No.: 170729-80-3
Name: Aprepitant
Article Data: 21
Cas Database
Molecular Structure:
Molecular Structure of 170729-80-3 (Aprepitant)
Formula: C23H21F7N4O3
Molecular Weight: 534.434
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: N/A
Flash Point: N/A
Solubility: N/A
Appearance: off-white to light yellow cyrstalline solid
Hazard Symbols: Xn,Xi
Risk Codes: R20/21/22; R36/37/38
Safety:
Transport Information: N/A
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
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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 .