Reaktionsgleichung
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:19]=[C:18](F)[CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])[N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li][N:29]([CH3:31])[CH3:30]>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:19]=[C:18]([N:29]([CH3:31])[CH3:30])[CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])[N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-4-fluorobenzoic acid (Example 248, 35 mg, 0.09 mmol) in THF (1 mL) at −40° C. was added LiNMe2 (0.19 mL, 1 M in hexanes) under nitrogen. The mixture was then stirred at this temperature for 30 min, and then gradually warmed to rt over a 4 h period. The pH of the solution was adjusted to pH 5, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude was purified by HPLC using gradient elution from 10 to 80% acetonitrile in water to afford 5.7 mg (15%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 9.55 (s, 1H), 7.73 (d, 1H), 7.22-7.35 (m, 4H), 6.44 (d, 1H), 6.18 (dd, 1H), 6.15 (s, 1H), 3.00 (s, 6H), 2.04 (s, 3H), 1.32 (s, 9H). ES-MS m/z 393.2 (MH30 ); HPLC RT (min) 2.84.
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude was purified by HPLC
- washelution from 10 to 80% acetonitrile in water
Quellen und Nachweise
- ORD-Eintrag
- ord-8c2db87082454790adc8c54f20ad1b7c
- Quelldatensatz
- uspto-grants-2007_09
- Patentnummer
- US07265144B2
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