(E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide

Base Information

• Chemical Name: (E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide
• CAS No.: 1245555-80-9
• Molecular Formula: C₁₉H₁₅BrClFN₄O₂
• Molecular Weight: 465.709
• Mol file: 1245555-80-9.mol

Synonyms:(E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide

Chemical Property of (E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide

There total 14 articles about (E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-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: 89.6%

N4-(3-chloro-4-fluorophenyl)-7-methoxyquinazoline-4,6-diamine (179552-75-1) + 4-bromocrotonyl chloride (99083-25-7) → (E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide (1245555-80-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;

Reference yield: 34.0%

N4-(3-chloro-4-fluorophenyl)-7-methoxyquinazoline-4,6-diamine (179552-75-1) + 4-bromocrotonic acid (13991-36-1) → (E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide (1245555-80-9)

Guidance literature:

With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/j.ejmech.2022.114100

Reference yield:

4-chloro-7-methoxy-6-nitroquinazoline (55496-69-0) → (E)-4-bromo-N-(4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)but-2-enamide (1245555-80-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / water; isopropyl alcohol; dichloromethane / 15 h / 50 °C

1.2: 0.08 h / 20 °C

2.1: hydrogen / ethyl acetate; ethanol; water / 1.75 h / 2068.65 Torr

3.1: triethylamine; N,N-dimethyl-formamide / tetrahydrofuran / 0.75 h / -20 °C / Sealed tube; Inert atmosphere

With hydrogenchloride; hydrogen; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; isopropyl alcohol;

DOI:10.1021/acs.jmedchem.6b00883

upstream raw materials:

N⁴-(3-chloro-4-fluorophenyl)-7-methoxyquinazoline-4,6-diamine

4-bromocrotonyl chloride

N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-nitroquinazolin- 4-amine

Downstream raw materials:

(2E)-N-[4-(3-chloro-4-fluoroanilino)-7-methoxy-6-quinazolinyl]-4-(dimethylamino)-2-butenamide

(E)-N-[4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yl]-4-[2-azaspiro[ 3.4]octan-2-yl]-2-butenamide