Dimethylformamide → ethyl 1-benzyl-3-[(6-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-pyridinyl)methoxy]-1H-pyrazole-4-carboxylate

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Reaktionsgleichung

Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[O:14][C:15]=2[CH3:16])=[N:7][CH:8]=1.[CH2:22]([N:29]1[CH:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:31]([OH:39])=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:22]([N:29]1[CH:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:31]([O:39][CH2:2][C:3]2[CH:8]=[N:7][C:6]([O:9][CH2:10][C:11]3[N:12]=[C:13]([C:17]4[O:18][CH:19]=[CH:20][CH:21]=4)[O:14][C:15]=3[CH3:16])=[CH:5][CH:4]=2)=[N:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 5-chloromethyl-2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}pyridine (1.30 g), ethyl 1-benzyl-3-hydroxy-1H-pyrazole-4-carboxylate (1.06 g), potassium carbonate (0.59 g) and N,N-dimethylformamide (50 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration to give ethyl 1-benzyl-3-[(6-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-pyridinyl)methoxy]-1H-pyrazole-4-carboxylate as colorless crystals (2.00 g, yield 90%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 140-141° C.

Aufarbeitung

filtrationthe precipitated crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-643568c240a945c6b44e7a8a54b358c1
Quelldatensatz: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07368578B2

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