Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N-]1C=CN=C1.[CH2:16]([C:20]1[C:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:38](=[O:41])(=[O:40])[NH2:39])=[CH:28][C:27]=2[F:42])=[C:23]([C:43]#[N:44])[N:22]([C:45]2[CH:50]=[C:49]([NH:51][C:52](=[O:55])[CH2:53][CH3:54])[CH:48]=[CH:47][C:46]=2[Cl:56])[N:21]=1)[CH2:17][CH2:18][CH3:19]>>[CH2:16]([C:20]1[C:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:38](=[O:41])(=[O:40])[NH:39][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])=[CH:28][C:27]=2[F:42])=[C:23]([C:43]#[N:44])[N:22]([C:45]2[CH:50]=[C:49]([NH:51][C:52](=[O:55])[CH2:53][CH3:54])[CH:48]=[CH:47][C:46]=2[Cl:56])[N:21]=1)[CH2:17][CH2:18][CH3:19]Komponenten
Edukt 3
Produkt 1
Versuchsvorschrift
By the procedure of Example 1, Step H, 2-chlorobenzoic acid was converted to its imidazolide and reacted with 3-n-butyl-1-[2-chloro-5-(propionylamino)phenyl]-4-[[3-fluoro-2'-sulfamoylbiphenyl-4-yl]methyl]-1H-pyrazole-5-carbonitrile (from Step K). The crude product was purified by semipreparative HPLC on a Zorbax C8 reverse phase column (elution with 75:25 acetonitrile-H2O containing 0.1% TFA), affording a 74% yield of the title compound as a cream-colored, stiff foam; homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 732 (M+1)+. 400 MHz 1H NMR (CDCl3) δ0.93 (t, J=7.3 Hz, 3H), 1.22 (t, J=7.5 Hz, 3H), 1.40 (m, 2H), 1.68 (m, 2H), 2.39 (q, J=7.5 Hz, 2H), 2.67 (t, J=7.8 Hz, 2H), 3.93 (br s, 2H), 7.1-7.7 (m, 12H), 7.77 (d, J=2.3 Hz, 1H), 8.37 (dd, J=7.9, 1.4 Hz, 1H), 9.10 (s, 1H).
Aufarbeitung
- customThe crude product was purified by semipreparative HPLC on a Zorbax C8 reverse phase column (elution with 75:25 acetonitrile-H2O containing 0.1% TFA)
Quellen und Nachweise
- ORD-Eintrag
- ord-bae3e48786044754af21054ebfdf0a59
- Quelldatensatz
- uspto-grants-1993_11
- Patentnummer
- US05262412
Verknüpfte Notizen
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