(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

Base Information

Chemical Name:(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide
CAS No.:1369764-76-0
Molecular Formula:C₂₂H₁₉F₃N₄O₂
Molecular Weight:428.414
Hs Code.:

Synonyms:(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

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Chemical Property of (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

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Technology Process of (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

There total 11 articles about (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide 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: 53.4%

: (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid

: 21717-96-4
2-amino-5-fluoropyridine

: 1369764-76-0
(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

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 - 60 ℃;
DOI:10.1021/acs.jmedchem.5b00217

Reference yield:

: C₁₇H₁₆F₂N₂O₂

: 1369764-76-0
(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

Guidance literature:: Multi-step reaction with 2 steps

1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; acetone / 2 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 - 60 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 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 water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/acs.jmedchem.5b00217

Reference yield:

: (1S,2R)-1-(3,4-difluorophenyl)cyclopropan-1,2-dimethanol

: 1369764-76-0
(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3,4-difluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: lipase acrylic resin from Candida antarctica / tetrahydrofuran / 17 h / 20 °C / Cooling with ice; Enzymatic reaction

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 - 20 °C

3.1: sodium hydroxide / ethanol; water / 1 h

4.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C

4.2: 1 h / -78 - 20 °C

5.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; acetone / 2 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 - 60 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; di-isopropyl azodicarboxylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 2.1: |Mitsunobu Displacement / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;
DOI:10.1021/acs.jmedchem.5b00217