Tetrabutylammonium Fluoride → HCID 178461061, compound
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][C:30]1[C:38]2[C:33](=[N:34][CH:35]=[C:36]([NH:39][C:40](=[O:56])[C:41]3[C:46]([F:47])=[CH:45][CH:44]=[C:43]([NH:48][S:49]([CH2:52][CH2:53][CH3:54])(=[O:51])=[O:50])[C:42]=3[F:55])[CH:37]=2)[NH:32][N:31]=1)(C(C)(C)C)(C)C>C1COCC1>[F:55][C:42]1[C:43]([NH:48][S:49]([CH2:52][CH2:53][CH3:54])(=[O:51])=[O:50])=[CH:44][CH:45]=[C:46]([F:47])[C:41]=1[C:40]([NH:39][C:36]1[CH:37]=[C:38]2[C:30]([CH2:29][CH2:28][CH2:27][OH:26])=[N:31][NH:32][C:33]2=[N:34][CH:35]=1)=[O:56]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Tetra-n-butylammonium fluoride (“TBAF”; 0.12 mL, 0.12 mmol, 1.0M in THF) was added to a solution of N-(3-(3-(tert-butyldimethylsilyloxy)propyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.034 g, 0.060 mmol) in THF (4.0 mL), and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated, and the crude product was purified by column chromatography, eluting with ethyl acetate, ethyl acetate/MeOH (50:1) to give 2,6-difluoro-N-(3-(3-hydroxypropyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.014 g, 52%) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.7 (s, 1H), 8.6 (s, 1H), 7.7 (m, 1H), 7.1 (m, 1H), 3.7 (t, J=7.0 Hz, 2H), 3.1-3.0 (m, 4H), 2.1 (m, 2H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-neg) M−1=452.3.
Workup
- concentrationThe reaction mixture was concentrated
- customthe crude product was purified by column chromatography
- washeluting with ethyl acetate, ethyl acetate/MeOH (50:1)
Sources & evidence
- ORD record
- ord-8fb185360e5a4793b60e30bbc7a97f11
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394795B2
Reaction notes
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