Trifluoroacetic acid → 4-Cyano-1H-imidazole-2-carboxylic acid [4-(1-azido-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide
Reaktionsgleichung
[C:1]1([C:7]2[CH:12]=[C:11]([C:13](O)([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=2[NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[N-:27]=[N+:28]=[N-:29].[Na+].C(O)(C(F)(F)F)=O.CCOC(C)=O>C(Cl)(Cl)Cl>[N:27]([C:13]([C:11]1[CH:10]=[CH:9][C:8]([NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])=[C:7]([C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)[CH:12]=1)([CH3:15])[CH3:14])=[N+:28]=[N-:29]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-amide (as prepared in example 12, 15.0 mg, 0.0428 mmol) and NaN3 (27.8 mg, 0.428 mmol) in 1 mL of chloroform at 0° C. under Ar was added TFA (49 μL, 0.642 mmol). The resulting mixture was stirred at 0° C. for 1 h under Ar. Treated with 30 mL of EtOAc, the mixture was washed with saturated NaHCO3 aqueous solution (10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (0-5% EtOAc/DCM) gave 13.6 mg (84%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C20H21N7O, 376.2 (M+H), found 376.0.
Aufarbeitung
- washthe mixture was washed with saturated NaHCO3 aqueous solution (10 mL), brine (10 mL)
- dry with materialdried (Na2SO4)
- customRemoval of the solvent under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-202b08c888e840d3b187de7a10c91941
- Quelldatensatz
- uspto-grants-2010_09
- Patentnummer
- US07790724B2
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