Dimethyl Sulfoxide → 1-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

HRID 919092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919092
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[N:23][N:24]([CH3:30])[C:25]=4[CH:26]([OH:29])[C:27]#[CH:28])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:31]([N:38]=[N+:39]=[N-:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CS(C)=O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2].CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[N:23][N:24]([CH3:30])[C:25]=4[CH:26]([C:27]4[N:40]=[N:39][N:38]([CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH:28]=4)[OH:29])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

8

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 866970911-{4'-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 679596491-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Versuchsvorschrift

1-{4′-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.17 g, 0.45 mmol) and benzyl azide (0.072 g, 0.54 mmol) were combined DMSO (5 mL). Copper(II) sulfate (0.001 g, 0.005 mmol) and sodium ascorbate (0.001 g, 0.05 mmol) were combined in H2O (2 mL) and the solution was added to the DMSO mixture. The reaction was stirred at room temperature for 18 hours then submitted to EtOAc/H2O workup. Purification on silica gel (0-70% EtOAc in hexanes) provided the title compound.

Aufarbeitung

  1. customPurification on silica gel (0-70% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b503df4c22b2428b84c04444e54d3af1
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09272990B2

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