9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one

Base Information

• Chemical Name: 9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one
• CAS No.: 1350816-54-4
• Molecular Formula: C₂₃H₂₃ClFN₅O
• Molecular Weight: 439.92
• Mol file: 1350816-54-4.mol

Synonyms:

Chemical Property of 9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one

There total 9 articles about 9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one 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: 39.0%

2-amino-9-chloro-5H-benzo[b]pyrimido[4,5-d]azepin-6(7H)-one + 3-(5-bromo-2-fluorophenyl)-N,N-dimethylpropan-1-amine (1350816-53-3) → 9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1350816-54-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium tert-butylate; XPhos; In tert-butyl alcohol; at 120 ℃; Microwave irradiation; Sealed tube; Inert atmosphere;

DOI:10.1021/jm2011172

Reference yield:

2-amino-4-chloro-benzoic acid methyl ester (5900-58-3) → 9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1350816-54-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 10 °C

2.2: 20 °C / pH 4

3.1: water / dimethyl sulfoxide / 150 °C / Cooling

3.2: 0 °C

4.1: tetrahydrofuran / 2 h / 60 °C / Inert atmosphere

5.1: potassium carbonate / ethanol / 75 °C

6.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium tert-butylate; XPhos / tert-butyl alcohol / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium tert-butylate; water; potassium carbonate; N-ethyl-N,N-diisopropylamine; XPhos; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol; 2.1: Dieckmann reaction / 6.1: Buchwald coupling;

DOI:10.1021/jm2011172

Reference yield:

3-(5-bromo-2-fluorophenyl)acrylic acid (202865-71-2) → 9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1350816-54-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C

2.1: hydrogen; pyrographite; sulfur; platinum / methanol / 1 h / 20 °C

3.1: borane-THF / tetrahydrofuran / 2 h / 50 °C

3.2: 2 h / 80 °C

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium tert-butylate; XPhos / tert-butyl alcohol / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; borane-THF; potassium tert-butylate; hydrogen; pyrographite; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; sulfur; N-ethyl-N,N-diisopropylamine; platinum; XPhos; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 4.1: Buchwald coupling;

DOI:10.1021/jm2011172

upstream raw materials:

2-amino-4-chloro-benzoic acid methyl ester

3-(5-bromo-2-fluorophenyl)acrylic acid

3-(5-bromo-2-fluorophenyl)-N,N-dimethylpropan-1-amine

methyl N-(3-carbomethoxypropionyl)-4-chloroanthranilate

Downstream raw materials:

9-chloro-2-({3-[3-(dimethylamino)propyl]-4-fluorophenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepine-6-thione