1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide

Base Information

• Chemical Name: 1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide
• CAS No.: 403825-23-0
• Molecular Formula: C₁₇H₂₁FN₄OS
• Molecular Weight: 348.444
• Mol file: 403825-23-0.mol

Synonyms:1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide

Chemical Property of 1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide

There total 12 articles about 1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide 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:

4-bromo-3-fluorotoluene (452-74-4) → 1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide (403825-23-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 88 percent / aq. KMnO₄; pyridine / 90 °C

2.1: 98 percent / borane-THF complex / tetrahydrofuran / 10 - 20 °C

3.1: 75 percent / Pd(PPh₃)4 / dimethylformamide / 18 h / 95 °C

4.1: 90 percent / Et₃N; DMSO; pyridine*SO₃ / CH₂Cl₂ / 2 h / 5 - 20 °C

5.1: EtMgBr / CH₂Cl₂ / 3 h / 20 °C

5.2: 98 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

6.1: 100 percent / pyridine / dimethylformamide / 3 h

7.1: ethyl acetate / 60 °C

8.1: 0.838 g / MeOH / 1 h / Heating

9.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

10.1: 19.6 g / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

11.1: 79 percent / titanium(IV) ethoxide / tetrahydrofuran / 168 h / 75 °C

12.1: tetrahydrofuran; diethyl ether / 0 °C

With pyridine; methanol; manganese(IV) oxide; titanium(IV) tetraethanolate; sodium hydroxide; potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; ethylmagnesium bromide; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.2: Grignard reaction / 12.1: Grignard reaction;

DOI:10.1021/jm020587n

Reference yield:

2-fluoro-4-(hydroxymethyl)benzonitrile (222978-02-1) → 1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide (403825-23-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / Et₃N; DMSO; pyridine*SO₃ / CH₂Cl₂ / 2 h / 5 - 20 °C

2.1: EtMgBr / CH₂Cl₂ / 3 h / 20 °C

2.2: 98 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

3.1: 100 percent / pyridine / dimethylformamide / 3 h

4.1: ethyl acetate / 60 °C

5.1: 0.838 g / MeOH / 1 h / Heating

6.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

7.1: 19.6 g / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

8.1: 79 percent / titanium(IV) ethoxide / tetrahydrofuran / 168 h / 75 °C

9.1: tetrahydrofuran; diethyl ether / 0 °C

With pyridine; methanol; manganese(IV) oxide; titanium(IV) tetraethanolate; sodium hydroxide; ethylmagnesium bromide; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Swern oxidation / 2.2: Grignard reaction / 9.1: Grignard reaction;

DOI:10.1021/jm020587n

Reference yield:

4-bromo-3-fluorobenzyl alcohol (222978-01-0) → 1-(S)-N-[1-(4-cyano-3-fluorophenyl)-1-(3-methyl-3H-imidazol-4-yl)ethyl]-2-methyl-[S(R)]-propanesulfinamide (403825-23-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 75 percent / Pd(PPh₃)4 / dimethylformamide / 18 h / 95 °C

2.1: 90 percent / Et₃N; DMSO; pyridine*SO₃ / CH₂Cl₂ / 2 h / 5 - 20 °C

3.1: EtMgBr / CH₂Cl₂ / 3 h / 20 °C

3.2: 98 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

4.1: 100 percent / pyridine / dimethylformamide / 3 h

5.1: ethyl acetate / 60 °C

6.1: 0.838 g / MeOH / 1 h / Heating

7.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

8.1: 19.6 g / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

9.1: 79 percent / titanium(IV) ethoxide / tetrahydrofuran / 168 h / 75 °C

10.1: tetrahydrofuran; diethyl ether / 0 °C

With pyridine; methanol; manganese(IV) oxide; titanium(IV) tetraethanolate; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ethylmagnesium bromide; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: Swern oxidation / 3.2: Grignard reaction / 10.1: Grignard reaction;

DOI:10.1021/jm020587n

upstream raw materials:

methylmagnesium bromide

4-bromo-3-fluorotoluene

4-bromo-3-fluorobenzyl alcohol

2-fluoro-4-(hydroxymethyl)benzonitrile