2-bromo-N-(3-hydroxy-2,2-dimethylpropyl)benzenesulfonamide → 4'-(5-Amino-3-cyanopyrazin-2-yl)-3'-fluoro-N-(3-hydroxy-2,2-dimethylpropyl)biphenyl-2-sulfonamide

HRID 1524124Notes

Reaction equation

HRID 1524124 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1.Br[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([NH:36][CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][OH:40])(=[O:35])=[O:34]>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:27]3[C:28]([S:33]([NH:36][CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][OH:40])(=[O:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 37154162-bromo-N-(3-hydroxy-2,2-dimethylpropyl)benzenesulfonamideHCID 90312891HCID 90312891, compound

Product 1

HCID 903139994'-(5-Amino-3-cyanopyrazin-2-yl)-3'-fluoro-N-(3-hydroxy-2,2-dimethylpropyl)biphenyl-2-sulfonamide

Procedure

The title compound was prepared using conditions analogous to those used to make Example 6 utilizing 6-amino-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile and 2-bromo-N-(3-hydroxy-2,2-dimethylpropyl)benzenesulfonamide. MS (ESI): mass calcd. for C22H22FN5OS, 455.14; m/z found, 456.0 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 8.26 (s, 1H), 7.93 (dd, J=7.8, 1.5, 1H), 7.72-7.60 (m, 3H), 7.47 (dd, J=7.4, 1.5, 1H), 7.43-7.34 (m, 5H), 4.49 (t, J=5.4, 1H), 3.08 (d, J=5.4, 2H), 2.62 (d, J=6.5, 2H), 0.73 (s, 6H).

Sources & evidence

ORD record
ord-b9b7d02576cc40eaa2f789f2d3c9e5bf
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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