Tetrabutylammonium Fluoride → HCID 86726514, compound

HRID 1487687Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1([F:68])[CH2:23][CH:22]([O:24][C:25]2[C:26]3[C:49]([C:50]4[CH:55]=[CH:54][C:53]([C:56](=[O:59])[NH:57][CH3:58])=[CH:52][CH:51]=4)=[CH:48][N:47](COCC[Si](C)(C)C)[C:27]=3[N:28]=[C:29]([NH:31][C:32]3[CH:44]=[CH:43][C:35]([C:36]([NH:38][CH:39]4[CH2:42][O:41][CH2:40]4)=[O:37])=[CH:34][C:33]=3[O:45][CH3:46])[N:30]=2)[CH2:21]1>C1COCC1>[F:68][C:20]1([F:19])[CH2:21][CH:22]([O:24][C:25]2[C:26]3[C:49]([C:50]4[CH:55]=[CH:54][C:53]([C:56](=[O:59])[NH:57][CH3:58])=[CH:52][CH:51]=4)=[CH:48][NH:47][C:27]=3[N:28]=[C:29]([NH:31][C:32]3[CH:44]=[CH:43][C:35]([C:36]([NH:38][CH:39]4[CH2:40][O:41][CH2:42]4)=[O:37])=[CH:34][C:33]=3[O:45][CH3:46])[N:30]=2)[CH2:23]1

Participants

Conditions

Temperature: 50 °C

Procedure

Tetrabutylammonium fluoride (5 equiv) was added to a stirred solution of 4-((4-(3,3-difluorocyclobutoxy)-5-(4-(methylcarbamoyl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-N-(oxetan-3-yl)benzamide (1 equiv) in THF (20 mL). The resulting mixture was capped and stirred at 50° C. for 16 h. The crude product was purified to afford the title compound (53.9% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.99 (s, 1H) 8.97 (d, J=6.62 Hz, 1H) 8.57 (d, 1H) 8.41 (d, J=4.41 Hz, 1H) 7.87 (d, J=10.09 Hz, 2H) 7.81 (d, 2H) 7.60 (d, 1H) 7.57-7.62 (m, 1H) 7.50 (d, J=2.21 Hz, 1H) 5.31-5.43 (m, 1H) 4.99-5.09 (m, 1H) 4.81 (t, J=6.94 Hz, 2H) 4.63 (t, J=6.31 Hz, 2H) 3.99 (s, 3H) 3.25 (br. s., 2H) 2.73-2.90 (m, 5H). MS (ESI) m/z 579.0 [M+1]+.

Workup

customThe resulting mixture was capped
customThe crude product was purified

Sources & evidence

ORD record: ord-19afd6abffb542d99e524f5930c88381
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428509B2

Reaction notes

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