3-Aminophenol → 1-(3-(2-Fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea

HRID 1917727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917727
[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)[O:7][N:6]=1)([CH3:4])[CH3:3].[NH2:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1.CN(C1C=CC=CN=1)C>C1COCC1>[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[O:19])[O:7][N:6]=1)([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 115683-AminophenolHCID 218852-DimethylaminopyridineHCID 66876626Phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate

Produkt 1

HCID 668757701-(3-(2-Fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)ureaAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To THF (10 mL) was added phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate from the previous step (500 mg, 1.9 mmol), 3-aminophenol (207 mg, 1.9 mmol) and dimethylaminopyridine (60 mg, 0.5 mmol) and the mixture stirred overnight at room temperature. The mixture was concentrated in vacuo and purified by chromatography on silica gel (10-50% EtOAc/hexanes) to afford 1-(3-(2-fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea (390 mg, 1.4 mmol, 74%). LC-MS (ESI) m/z 280 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by chromatography on silica gel (10-50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ae15f05d79d14012966f779a1b1a747b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618289B2

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