Ammonium Acetate → HCID 178502204, Verbindung
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:34])[NH:4][CH:5]([C:9]([N:11]1[CH:15]([C:16](=O)[NH:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)=O)[CH2:14][N:13]([CH2:29][C:30]([F:33])([F:32])[F:31])[CH2:12]1)=[O:10])[CH:6]([CH3:8])[CH3:7].C([O-])(=O)C.[NH4+:39]>>[CH3:1][O:2][C:3](=[O:34])[NH:4][CH:5]([C:9]([N:11]1[CH:15]([C:16]2[NH:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)[N:39]=2)[CH2:14][N:13]([CH2:29][C:30]([F:31])([F:33])[F:32])[CH2:12]1)=[O:10])[CH:6]([CH3:8])[CH3:7]Komponenten
Reaktionsbedingungen
- Temperatur
- 135 °C
Versuchsvorschrift
{1-[5-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-3-(2,2,2-trifluoro-ethyl)-imidazolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (148 mg, <257 mmol) was dissolved in m-xylenes (4.0 mL) and heated at 135° C. Solid ammonium acetate (150 mg, 1.9 mmol) was added and the reaction was stirred at 135° C. After 60 minutes, the reaction was cooled to room temperature and the volatiles were removed in vacuo. The crude material was purified via RP-HPLC (eluent: water/MeCN w 0.1% TFA) to yield the product {1-[4-(4-Bromo-phenyl)-1′-(2,2,2-trifluoro-ethyl)-1′,2′,4′,5′-tetrahydro-1H-[2,4′]biimidazolyl-3′-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (15.1 mg) as the TFA salt: LCMS-ESI+: calc'd for C21H25BrF3N5O3: 532.3 (M+). Found: 532.1/534.2 (M+).
Aufarbeitung
- temperaturethe reaction was cooled to room temperature
- customthe volatiles were removed in vacuo
- customThe crude material was purified via RP-HPLC (eluent: water/MeCN w 0.1% TFA)
Quellen und Nachweise
- ORD-Eintrag
- ord-1de9d0876a8746199bfff2ff58f99b56
- Quelldatensatz
- uspto-grants-2014_03
- Patentnummer
- US08669234B2
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