Defluoro Aprepitant

Base Information

• Chemical Name: Defluoro Aprepitant
• CAS No.: 170729-76-7
• Molecular Formula: C23H22F6N4O3
• Molecular Weight: 516.43600
• Hs Code.: 2934990002
• Mol file: 170729-76-7.mol

Synonyms:5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-phenylmorpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one;5-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-phenyl-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one;

Chemical Property of Defluoro Aprepitant

Chemical Property:

• PKA: 8.09±0.20(Predicted)
• PSA: 83.50000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 5.16320

Purity/Quality:

99%+, ^*data from raw suppliers

DefluoroAprepitant ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: NK-1 receptor antagonists for treating severe anxiety disorders. Antidepressant Defluoro Aprepitant (Aprepitant EP Impurity A) is a NK-1 receptor antagonists for treating severe anxiety disorders. Antidepressant.

Technology Process of Defluoro Aprepitant

There total 12 articles about Defluoro Aprepitant which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

(2-{(2R,3S)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-phenyl-morpholin-4-yl}-1-hydrazono-ethyl)-carbamic acid methyl ester → aprepitant (170729-76-7)

Guidance literature:

In xylene; for 2h; Heating;

DOI:10.1021/jm980299k

Reference yield:

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride (785-56-8) → 5-{(2R,3S)-2-[(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-phenyl-morpholin-4-ylmethyl}-2,4-dihydro-[1,2,4]triazol-3-one (170729-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) L-Selectride / 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 30 min

2: 69 percent / tetrahydrofuran; toluene / 18 h / Heating

3: 9 percent / H₂ / 10percent Pd/C / ethyl acetate; propan-2-ol / 48 h

4: DIEA / acetonitrile / 20 h / Ambient temperature

5: xylene / 2 h / Heating

With hydrogen; L-Selectride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; xylene;

DOI:10.1021/jm980299k

Reference yield:

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride (785-56-8) → aprepitant (170729-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) L-Selectride / 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 30 min

2: 69 percent / tetrahydrofuran; toluene / 18 h / Heating

3: 75 percent / H₂ / 10percent Pd/C / ethyl acetate; propan-2-ol / 48 h

4: 91 percent / DIEA / acetonitrile / 20 h / Ambient temperature

5: 76 percent / xylene / 2 h / Heating

With hydrogen; L-Selectride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; xylene;

DOI:10.1021/jm980299k

upstream raw materials:

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

(S)-4-benzyl-3-phenylmorpholin-2-one

2-(R)-(1-(3,5-bis(tri-fluoromethyl)phenyl)ethenyloxy)-3-(S)-phenyl-4-benzyl morpholine

2-(R)-(3,5-bis(tri-fluoro-methyl)benzoyloxy)-3-(S)-phenyl-4-benzyl morpholine

Refernces