1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one

Base Information

• Chemical Name: 1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one
• CAS No.: 1311263-80-5
• Molecular Formula: C₂₇H₃₁ClN₄O₃
• Molecular Weight: 495.021

Synonyms:1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one

Chemical Property of 1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one

Chemical Property:

Purity/Quality:

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Technology Process of 1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one

There total 11 articles about 1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-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: 77.0%

1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-bromo-2,2-dimethylspiro-[chroman-4,4′-imidazol]-5′(1′H)-one (1430416-62-8) + 3-chlorophenylboronic acid (63503-60-6) → 1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (1311263-80-5)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In water; at 90 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jm4002154

Reference yield:

2′-amino-6-bromo-1′,2,2-trimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (1212010-85-9) → 1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (1311263-80-5)

Guidance literature:

Multi-step reaction with 6 steps

1: N,N-dimethyl-formamide / 18 h / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 60 - 90 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

4: triethylamine / dichloromethane / 2 h / 20 °C

5: ammonia / methanol / 100 h / 50 - 60 °C / Sealed tube

6: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water / 1.5 h / 90 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonia; sodium carbonate; potassium carbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 6: |Suzuki Coupling;

DOI:10.1021/jm4002154

Reference yield:

6-bromo-2,2-dimethylchroman-4-one (99853-21-1) → 1′-((1-acetylpiperidin-4-yl)methyl)-2′-amino-6-(3-chlorophenyl)-2,2-dimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (1311263-80-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 72 h / 70 - 110 °C / Inert atmosphere; Autoclave

2: N,N-dimethyl-formamide / 1 h / 20 °C / Alkaline conditions

3: Lawessons reagent / toluene / 12 h / Reflux

4: tert.-butylhydroperoxide; ammonium hydroxide / methanol / 2 h / 40 °C

5: N,N-dimethyl-formamide / 18 h / 20 °C

6: potassium carbonate / N,N-dimethyl-formamide / 60 - 90 °C

7: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

8: triethylamine / dichloromethane / 2 h / 20 °C

9: ammonia / methanol / 100 h / 50 - 60 °C / Sealed tube

10: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water / 1.5 h / 90 °C / Inert atmosphere

With Lawessons reagent; tert.-butylhydroperoxide; ammonium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonia; sodium carbonate; potassium carbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: |Bucherer-Bergs Reaction / 10: |Suzuki Coupling;

DOI:10.1021/jm4002154

upstream raw materials:

2′-amino-6-bromo-1′,2,2-trimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one

(E)-N′-(6-bromo-2,2-dimethyl-5′-oxo-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-2′-yl)-N,N-dimethylformimidamide

(E)-N′-(6-bromo-2,2-dimethyl-5′-oxo-1′-(piperidin-4-ylmethyl)-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-2′-yl)-N,N-dimethylformimidamide

(E)-N′-(1′-((1-acetylpiperidin-4-yl)methyl)-6-bromo-2,2-dimethyl-5′-oxo-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-2′-yl)-N,N-dimethylformimidamide

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