(S)-5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-((1-hydroxy-3,3-dimethylbutan-2-yl)amino)nicotinonitrile → (S)-5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-((1-hydroxy-3,3-dimethylbutan-2-yl)amino)nicotinonitrile

HRID 1055087Notes

Reaction equation

HRID 1055087 reaction equation
FC1C(N[C@@H](C(C)(C)C)CO)=NC(C2C3C(=NC=C(F)C=3)NC=2)=NC=1.[F:26][C:27]1[C:28]([NH:55][C@@H:56]([C:59]([CH3:62])([CH3:61])[CH3:60])[CH2:57][OH:58])=[N:29][C:30]([C:35]2[C:43]3[C:38](=[N:39][CH:40]=[C:41]([F:44])[CH:42]=3)[N:37](S(C3C=CC(C)=CC=3)(=O)=O)[CH:36]=2)=[C:31]([CH:34]=1)[C:32]#[N:33]>>[F:26][C:27]1[C:28]([NH:55][C@@H:56]([C:59]([CH3:62])([CH3:61])[CH3:60])[CH2:57][OH:58])=[N:29][C:30]([C:35]2[C:43]3[C:38](=[N:39][CH:40]=[C:41]([F:44])[CH:42]=3)[NH:37][CH:36]=2)=[C:31]([CH:34]=1)[C:32]#[N:33]

Participants

3

Reactant 2

HCID 71247622(S)-5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-((1-hydroxy-3,3-dimethylbutan-2-yl)amino)nicotinonitrileHCID 71251247(S)-2-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)-3,3-dimethylbutane-1-ol

Product 1

HCID 71248010(S)-5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-((1-hydroxy-3,3-dimethylbutan-2-yl)amino)nicotinonitrile

Procedure

Alcohol, 24, was synthesized in a manner similar to compound 32 utilizing the same deprotection procedure, starting with compound 98a: 1H NMR (400 MHz, CDCl3) δ 10.27 (brs, 1H), 8.25 (d, J=9.4 Hz, 1H), 8.17 (s, 1H), 8.11 (s, 1H), 7.23 (d, J=10.3 Hz, 1H), 5.20 (d, J=9.6 Hz, 1H), 4.41 (t, J=7.4 Hz, 1H), 4.09 (d, J=11.3 Hz, 1H), 3.82-3.58 (m, 1H), 0.99 (d, J=19.5 Hz, 9H).

Sources & evidence

ORD record
ord-9d35a60f5ec44c73b1c4e2642efd067d
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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