(Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide

Base Information

• Chemical Name: (Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide
• CAS No.: 1420404-16-5
• Molecular Formula: C₂₄H₂₄ClF₂N₅O₃
• Molecular Weight: 503.936
• Mol file: 1420404-16-5.mol

Synonyms:

Chemical Property of (Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide

There total 3 articles about (Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide 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: 45.5%

2-(dimethylamino)-acetaldehyde hydrochloride (125969-54-2) + diethyl (2-((4-((3-chloro-4-fluorophenyl)amino)-7-(((S)-tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)amino)-1-fluoro-2-oxoethyl)phosphonate → (Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide (1420404-16-5) + (E)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide (1420404-20-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 0 - 20 ℃;

DOI:10.1021/jm5014659

Reference yield:

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline (314771-76-1,402855-03-2) → (Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide (1420404-16-5) + (E)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide (1420404-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / N,N-dimethyl-formamide / 0 - 20 °C

2: sodium hydroxide / ethanol; water / 0 - 20 °C

With triethylamine; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide; 2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/jm5014659

Reference yield:

4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline (314771-88-5,402855-07-6) → (Z)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide (1420404-16-5) + (E)-(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)-2-fluorobut-2-enamide (1420404-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol; dichloromethane / 1 h / 0 - 20 °C

2: triethylamine / N,N-dimethyl-formamide / 0 - 20 °C

3: sodium hydroxide / ethanol; water / 0 - 20 °C

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; triethylamine; sodium hydroxide; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 3: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/jm5014659

upstream raw materials:

2-(dimethylamino)-acetaldehyde hydrochloride

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline