4-amino-N-(1-(3-(4-[¹⁸F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide

Base Information

• Chemical Name: 4-amino-N-(1-(3-(4-[¹⁸F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide
• CAS No.: 1186220-76-7
• Molecular Formula: C₂₃H₃₀FN₃O₃
• Molecular Weight: 414.51

Synonyms:4-amino-N-(1-(3-(4-[¹⁸F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide

Chemical Property of 4-amino-N-(1-(3-(4-[¹⁸F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide

Chemical Property:

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Technology Process of 4-amino-N-(1-(3-(4-[¹⁸F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide

There total 10 articles about 4-amino-N-(1-(3-(4-[¹⁸F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide 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:

tert-butyl 4-(1-(3-(4-[18F]fluorophenoxy)propyl)-4-methylpiperidin-4-ylcarbamoyl)-3-methoxyphenylcarbamate (1186220-75-6) → 4-amino-N-(1-(3-(4-[18F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide (1186220-76-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 80 ℃; Inert atmosphere;

DOI:10.1002/jlcr.1565

Reference yield:

tert-butyl 3-methoxy-4-(4-methylpiperidin-4-ylcarbamoyl)phenylcarbamate (1186220-73-4) → 4-amino-N-(1-(3-(4-[18F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide (1186220-76-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 12 h / 20 °C

2: [18F]fluoride ion, cyclotron produced, NCA; tetraethylammonium bicarbonate; tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate) / butan-1-ol; N,N-dimethyl acetamide / 0.17 h / 110 °C / Sealed tube

3: trifluoroacetic acid / dichloromethane / 0.08 h / 80 °C

With tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate); potassium carbonate; tetraethylammonium bicarbonate; trifluoroacetic acid; potassium iodide; [18F]fluoride ion, cyclotron produced, NCA; In dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/acsmedchemlett.0c00658

Reference yield:

4-amino-2-methoxybenzoic acid (2486-80-8) → 4-amino-N-(1-(3-(4-[18F]fluorophenoxy)propyl)-4-methylpiperidin-4-yl)-2-methoxybenzamide (1186220-76-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / methanol / 6 h / 20 °C

2.1: triethylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

3.1: ammonium formate; palladium on activated charcoal / methanol / 3.5 h / 65 °C

4.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 12 h / 20 °C

5.1: [18F]fluoride ion, cyclotron produced, NCA; tetraethylammonium bicarbonate; tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate) / butan-1-ol; N,N-dimethyl acetamide / 0.17 h / 110 °C / Sealed tube

6.1: trifluoroacetic acid / dichloromethane / 0.08 h / 80 °C

With palladium on activated charcoal; tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate); benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonium formate; potassium carbonate; tetraethylammonium bicarbonate; triethylamine; trifluoroacetic acid; potassium iodide; [18F]fluoride ion, cyclotron produced, NCA; In methanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/acsmedchemlett.0c00658

upstream raw materials:

tert-butyl 4-(1-(3-(4-[¹⁸F]fluorophenoxy)propyl)-4-methylpiperidin-4-ylcarbamoyl)-3-methoxyphenylcarbamate

4-amino-2-methoxybenzoic acid

tert-butyl 4-(1-benzyl-4-methylpiperidin-4-ylcarbamoyl)-3-methoxyphenylcarbamate

tert-butyl 3-methoxy-4-(4-methylpiperidin-4-ylcarbamoyl)phenylcarbamate

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