Dimethylformamide → [2-Amino-6-(1-methyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone
Reaktionsgleichung
F[C:2](F)(F)C(O)=O.[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13]N=[C:11]([NH:26][CH:27]2[CH2:32]CNC[CH2:28]2)[N:10]=1.C(=O)([O-])[O-].[K+].[K+].IC.[CH3:41][N:42]([CH3:45])[CH:43]=O>C(OCC)(=O)C>[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13][CH:2]=[C:11]([NH:26][CH:27]2[CH2:28][CH2:43][N:42]([CH3:45])[CH2:41][CH2:32]2)[N:10]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt (0.0575 mmol, Example 22) in N,N-dimethylformamide (1.5 mL) were added potassium carbonate (55.6 mg, 0.4024 mmol, Aldrich) and iodomethane (14.8 mg, 0.104 mmol, Aldrich 99.5%) in N,N-dimethylformamide (0.35 mL). The reaction was stirred at 0° C. for 4 hrs. The resulting mixture was diluted with ethyl acetate (30 mL), washed with water, brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified on reversed phase HPLC to give [2-Amino-6-(1-methyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (4.8 mg, 24% yield). HRMS, observed: 358.1810, Calcd for M+: 358.1805.
Aufarbeitung
- washwashed with water, brine
- dry with materialdried over sodium sulfate
- customevaporated in vacuo
- customThe residue was purified on reversed phase HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-a5fd57a524414ea9b654591ec4def49b
- Quelldatensatz
- uspto-grants-2008_09
- Patentnummer
- US07423051B2
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