(1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide

Base Information

• Chemical Name: (1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide
• CAS No.: 1321964-74-2
• Molecular Formula: C₂₀H₂₁F₄N₃O₃S
• Molecular Weight: 459.465
• Mol file: 1321964-74-2.mol

Synonyms:(1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide

Chemical Property of (1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide

There total 12 articles about (1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide 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: 77.0%

N-{4-[(1R)-1-aminoethyl]-2-fluorophenyl}methanesulfonamide hydrochloride + (1S,2S)-2-methyl-2-(6-trifluoromethylpyridin3-yl)cyclopropanecarboxylic acid (1321964-76-4) → (1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide (1321964-74-2)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 55 ℃; for 2h; optical yield given as %de;

DOI:10.1021/op200177b

Reference yield:

5-bromo-2(trifluoromethyl)pyridine (436799-32-5) → (1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide (1321964-74-2)

Guidance literature:

Multi-step reaction with 6 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine / 12 h / 100 °C / 2585.81 Torr

2: tetrahydrofuran / 2 h / -10 °C

3: toluene-4-sulfonic acid / toluene / 6 h / Reflux

4: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; 2,6-bis[(4R)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-pyridine / dichloromethane; toluene / 5 h / 80 °C

5: water; lithium hydroxide / ethanol / 2 h / 30 °C

6: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 55 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,6-bis[(4R)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-pyridine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; water; toluene-4-sulfonic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/op200177b

Reference yield:

5-(prop-1-en-2-yl)-2-(trifluoromethyl)pyridine (910486-39-4) → (1S,2S)-N-[(1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl]-2-methyl-2-[6-(trifluoromethyl)pyridin3-yl]cyclopropanecarboxamide (1321964-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; 2,6-bis[(4R)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-pyridine / dichloromethane; toluene / 5 h / 80 °C

2: water; lithium hydroxide / ethanol / 2 h / 30 °C

3: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 55 °C

With 2,6-bis[(4R)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-pyridine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; water; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/op200177b

upstream raw materials:

(1S,2S)-2-methyl-2-(6-trifluoromethylpyridin3-yl)cyclopropanecarboxylic acid

3'-fluoro-4'-(methylsulfonylamino)acetophenone

2-(6-trifluoromethylpyridin-3-yl)propan-2-ol

5-(prop-1-en-2-yl)-2-(trifluoromethyl)pyridine