[¹⁸F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide

Base Information

• Chemical Name: [¹⁸F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
• CAS No.: 1621182-22-6
• Molecular Formula: C₂₄H₂₅ClFN₅O₃
• Molecular Weight: 484.947

Synonyms:[¹⁸F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide

Chemical Property of [¹⁸F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide

Chemical Property:

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Technology Process of [¹⁸F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide

There total 4 articles about [¹⁸F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)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:

7-chloro-6-nitro-4(3H)-quinazolinone (53449-14-2) → [18F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide (1621182-22-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N,N-dimethyl-formamide / 6 h / 90 °C

2.1: potassium tert-butylate / N,N-dimethyl-formamide; tert-butyl alcohol; tetrahydrofuran / 20 - 45 °C / Inert atmosphere

3.1: iron; acetic acid / ethanol; water / 0.33 h / 110 °C

4.1: N,N-dimethyl-formamide; oxalyl dichloride / tetrahydrofuran / 1.5 h / 0 - 25 °C / Inert atmosphere

4.2: 0 - 20 °C

5.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 0.5 h / 120 °C

With oxalyl dichloride; potassium tert-butylate; iron; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

(S,E)-4-(dimethylamino)-N-(4-oxo-7-((tetrahydrofuran-3-yl)oxy)-3,4-dihydroquinazolin-6-yl)but-2-enamide (1456696-14-2) + 3-chloro-4-[18F]fluoroaniline (906565-46-6) → [18F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide (1621182-22-6)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 0.5h;

Reference yield:

6-nitro-7-(phenylsulfonyl)quinazolin-4(3H)-one (1621182-16-8) → [18F](S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide (1621182-22-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide; tert-butyl alcohol; tetrahydrofuran / 20 - 45 °C / Inert atmosphere

2.1: iron; acetic acid / ethanol; water / 0.33 h / 110 °C

3.1: N,N-dimethyl-formamide; oxalyl dichloride / tetrahydrofuran / 1.5 h / 0 - 25 °C / Inert atmosphere

3.2: 0 - 20 °C

4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 0.5 h / 120 °C

With oxalyl dichloride; potassium tert-butylate; iron; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;

upstream raw materials:

(S,E)-4-(dimethylamino)-N-(4-oxo-7-((tetrahydrofuran-3-yl)oxy)-3,4-dihydroquinazolin-6-yl)but-2-enamide

3-chloro-4-[¹⁸F]fluoroaniline

7-chloro-6-nitro-4(3H)-quinazolinone

6-nitro-7-(phenylsulfonyl)quinazolin-4(3H)-one

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