Water → 1-(3,5-Bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-imidazole-4-carboxylic acid methyl ester

HRID 349270

Reaktionsgleichung

[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([C:18]#N)[N:9]=[CH:8]1.[OH2:29].S(=O)(=O)(O)O.[C:35]([O-])(O)=[O:36].[Na+]>CO>[CH3:35][O:36][C:18]([C:10]1[N:9]=[CH:8][N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:28])([F:27])[F:1])[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=2)[C:11]=1[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:29]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

In a pressure vessel dissolve 1-(3,5-Bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-imidazole-4-carbonitrile (0.043 g, 0.11 mmol) in MeOH (1 mL), add H2O (0.1 mL), and concentrated sulfuric acid (0.3 mL), and stir at 100° C. After 24 h., neutralize with sat. aq. NaHCO3, and extract with EtOAc (3×). Dry over MgSO4, filter, and concentrate. Purify by radial chromatography on silica gel to give the title compound: MS (ES) 430.2 (M+1); 1H NMR (300 MHz, CDCl3): δ 8.68 (ap d, 1H), 8.52 (ap d, 1H), 7.80 (s, 1H), 7.78 (s, 1H), 7.56 (d, J=7.8 Hz, 1H), 7.37 (m, 1H), 7.29 (s, 2H), 5.30 (s, 2H), 3.81 (s, 3H).

Aufarbeitung

extractionextract with EtOAc (3×)
dry with materialDry over MgSO4
filtrationfilter
concentrationconcentrate
customPurify by radial chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-37781fbf248e4980b6e6f700e9a536df
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07179804B2

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