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

Base Information

Chemical Name:5-amino-3-[4-(2,4-difluorophenoxy)phenyl]-1-{(3R)-1-[(2E)-4-hydroxybut-2-enoyl]-piperidin-3-yl}-1H-pyrazole-4-carboxamide
CAS No.:1609467-26-6
Molecular Formula:C₂₅H₂₅F₂N₅O₄
Molecular Weight:497.501
Hs Code.:

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

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

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

There total 14 articles about 5-amino-3-[4-(2,4-difluorophenoxy)phenyl]-1-{(3R)-1-[(2E)-4-hydroxybut-2-enoyl]-piperidin-3-yl}-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: 69.0%

: 24587-49-3
(2E)-4-hydroxybut-2-enoic acid

: 1609468-26-9
(R)-5-amino-3-(4-(2,4-difluorophenoxy)phenyl)-1-(piperidin-3-yl)-1H-pyrazole-4-carboxamide

: 1609467-26-6
5-amino-3-[4-(2,4-difluorophenoxy)phenyl]-1-{(3R)-1-[(2E)-4-hydroxybut-2-enoyl]-piperidin-3-yl}-1H-pyrazole-4-carboxamide

Guidance literature:: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/acsmedchemlett.8b00461

Reference yield:

: 1609467-65-3
4-(2,4-difluorophenoxy)benzoyl chloride

: 1609467-26-6
5-amino-3-[4-(2,4-difluorophenoxy)phenyl]-1-{(3R)-1-[(2E)-4-hydroxybut-2-enoyl]-piperidin-3-yl}-1H-pyrazole-4-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 3 h / 20 °C

1.3: 18 h / Reflux

2.1: ethanol / 3 h / 20 °C

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

4.1: ChiralPak OJ-H / ethanol

5.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

With water; sodium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

Reference yield:

: 1609467-66-4
2-((4-(2,4-difluorophenoxy)phenyl)(methoxy)methylene)-malononitrile

: 1609467-26-6
5-amino-3-[4-(2,4-difluorophenoxy)phenyl]-1-{(3R)-1-[(2E)-4-hydroxybut-2-enoyl]-piperidin-3-yl}-1H-pyrazole-4-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1: ethanol / 3 h / 20 °C

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

3: ChiralPak OJ-H / ethanol

4: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

With water; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In ethanol; N,N-dimethyl-formamide;