5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide

Base Information

• Chemical Name: 5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide
• CAS No.: 1609467-17-5
• Molecular Formula: C₂₅H₂₅F₂N₅O₃
• Molecular Weight: 481.502

Synonyms:5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide

Chemical Property of 5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide

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Technology Process of 5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide

There total 10 articles about 5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-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: 47.0%

(E)-but-2-enoic acid (107-93-7) + (R)-5-amino-3-(4-(2,4-difluorophenoxy)phenyl)-1-(piperidin-3-yl)-1H-pyrazole-4-carboxamide (1609468-26-9) → 5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide (1609467-17-5)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

DOI:10.1021/acsmedchemlett.8b00461

Reference yield:

2-((4-(2,4-difluorophenoxy)phenyl)(methoxy)methylene)-malononitrile (1609467-66-4) → 5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide (1609467-17-5)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / ethanol / 3 h / 20 °C

2: sodium hydroxide; water / ethanol / 24 h / 140 °C / Sealed tube

3: triethylamine / acetonitrile; methanol / Resolution of racemate

4: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 0 °C

With water; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00461

Reference yield:

4-(2,4-difluorophenoxy)benzoyl chloride (1609467-65-3) → 5-amino-1-{(3R)-1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-[4-(2,4-difluorophenoxy)phenyl]-1H-pyrazole-4-carboxamide (1609467-17-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C

1.3: 18 h / Reflux

2.1: triethylamine / ethanol / 3 h / 20 °C

3.1: sodium hydroxide; water / ethanol / 24 h / 140 °C / Sealed tube

4.1: triethylamine / acetonitrile; methanol / Resolution of racemate

5.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 0 °C

With water; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00461

upstream raw materials:

4-(2,4-difluorophenoxy)benzoyl chloride

2-((4-(2,4-difluorophenoxy)phenyl)(methoxy)methylene)-malononitrile

benzyl 3-(5-amino-4-cyano-3-(4-(2,4-difluorophenoxy)phenyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

5-amino-3-(4-(2,4-difluorophenoxy)phenyl)-1-(piperidin-3-yl)-1H-pyrazole-4-carboxamide

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