Tetrahydrofuran → HCID 57917350, Verbindung

HRID 69187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69187
C1COCC1.C([Si](C)(C)[O:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[CH:24]=[C:23]([C:25]3[CH:26]=[CH:27][C:28]4[N:29]([C:31]([CH2:34][C:35]5[CH:36]=[C:37]6[C:42](=[CH:43][C:44]=5[F:45])[N:41]=[CH:40][CH:39]=[CH:38]6)=[CH:32][N:33]=4)[N:30]=3)[CH:22]=[N:21]2)[CH2:16][CH2:15]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOC(C)=O>[F:45][C:44]1[CH:43]=[C:42]2[C:37]([CH:38]=[CH:39][CH:40]=[N:41]2)=[CH:36][C:35]=1[CH2:34][C:31]1[N:29]2[N:30]=[C:25]([C:23]3[CH:22]=[N:21][N:20]([CH:17]4[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][OH:11])[CH2:15][CH2:16]4)[CH:24]=3)[CH:26]=[CH:27][C:28]2=[N:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 686342406-[6-(1-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-piperidin-4-yl}-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-fluoro-quinoline

Produkt 1

HCID 57917350HCID 57917350, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A flask was charged with THF (5 mL), 6-[6-(1-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-piperidin-4-yl}-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-fluoro-quinoline (Stage 147.1, 96 mg, 0.164 mmol) and tetrabutylammonium fluoride (819 μL of a 1 M solution, 0.819 mmol). The mixture was stirred at rt for 2 h. The RM was diluted with EtOAc and washed with NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by MPLC, then taken up in NaHCO3 and extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound (tR 2.99 min (conditions 3), MH+=472.1, 1H-NMR in DMSO-d6: 8.84 (m, 1H); 8.50 (s, 1H); 8.34 (m, 1H); 8.08 (m, 2H); 8.06 (m, 1H); 7.76 (d, 1H); 7.60 (s, 1H); 7.53 (d, 1H); 7.47 (m, 1H); 4.55 (s, 2H); 4.41 (t, 1H); 3.50 (m, 2H); 2.97 (m, 2H); 2.42 (t, 2H); 2.13 (m, 2H); 1.97 (m, 4H)).

Aufarbeitung

  1. washwashed with NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by MPLC
  6. extractionextracted with DCM
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-61967bab7772420397ac4afea3f8cc72
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

Notizen zur Reaktion

Wird geladen…