Tetrahydrofuran → HCID 57917350, compound

HRID 69187Notes

Reaction equation

HRID 69187 reaction equation
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

Participants

5

Reactant 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

Product 1

HCID 57917350HCID 57917350, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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)).

Workup

  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

Sources & evidence

ORD record
ord-61967bab7772420397ac4afea3f8cc72
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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