N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide

Base Information

• Chemical Name: N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide
• CAS No.: 1558041-33-0
• Molecular Formula: C₂₇H₂₇N₅O₄
• Molecular Weight: 485.542

Synonyms:N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide

Chemical Property of N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide

Chemical Property:

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Technology Process of N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide

There total 5 articles about N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide 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: 89.0%

2-Methyl-5-phenyl-2H-pyrazole-3-carboxylic acid (10250-64-3) + (2S,4R)-4-amino-1-(benzofuran-3-carbonyl)-N-ethylpyrrolidine-2-carboxamide (1558040-97-3) → N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide (1558041-33-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 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 ℃;

DOI:10.1021/jm401326j

Reference yield:

(4R)-N-ethyl-4-({[(9H-fluoren-9-ylmethyl)oxy]carbonyl}amino)-L-prolinamide (1558041-82-9) → N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide (1558041-33-0)

Guidance literature:

Multi-step reaction with 3 steps

1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C

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

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

With piperidine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide;

DOI:10.1021/jm401326j

Reference yield:

(2S,4R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (176486-63-8) → N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide (1558041-33-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; water / 2 h

2: trifluoroacetic acid / dichloromethane / 5 h / 20 °C

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C

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

5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

With piperidine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm401326j

upstream raw materials:

(4R)-N-ethyl-4-({[(9H-fluoren-9-ylmethyl)oxy]carbonyl}amino)-L-prolinamide

2-Methyl-5-phenyl-2H-pyrazole-3-carboxylic acid

(2S,4R)-4-amino-1-(benzofuran-3-carbonyl)-N-ethylpyrrolidine-2-carboxamide

(2S,4R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

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