Acetonitrile--water (1/1) → (S)-2-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)-3,3-dimethylbutane-1-ol

HRID 1055064Notes

Reaction equation

HRID 1055064 reaction equation
[F:1][C:2]1[C:3]([NH:28][C@@H:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:30][OH:31])=C[C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)=[N:6][CH:7]=1.C(#[N:38])C.O>>[F:1][C:2]1[C:3]([NH:28][C@@H:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:30][OH:31])=[N:38][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 71247626(S)-2-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-4-ylamino)-3,3-dimethylbutan-1-ol

Product 1

HCID 71251247(S)-2-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)-3,3-dimethylbutane-1-ol

Procedure

Alcohol, 32, was synthesized in a manner similar to compound 70a utilizing the same deprotection procedure, starting with compound 54a: 1H NMR (400 MHz, CDCl3) δ 10.77 (brs, 1H), 8.25 (d, J=8.4 Hz, 1H), 8.07 (s, 1H), 8.03 (s, 1H), 7.88 (s, 1H), 5.59 (brs, 1H), 4.36 (t, J=8.3 Hz, 2H), 4.11 (m, 1H), 3.72 (m, 2H), 1.06 (s, 9H); LC/MS (10-90% ACN/water 5 min with 0.9% FA) m/z 348.13 (M+H) RT=1.83 minutes.

Sources & evidence

ORD record
ord-e23a5af938fc4fb8bb08031917fcef1c
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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