2-Bromo-N-(2-hydroxyethyl)-5-(trifluoromethyl)benzenesulfonamide → 4'-(5-Amino-3-cyanopyrazin-2-yl)-3'-fluoro-N-(2-hydroxyethyl)-4-(trifluoromethyl)biphenyl-2-sulfonamide

HRID 1524122Notes

Reaction equation

HRID 1524122 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][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=1[S:37]([NH:40][CH2:41][CH2:42][OH:43])(=[O:39])=[O:38]>>[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:37]([NH:40][CH2:41][CH2:42][OH:43])(=[O:38])=[O:39])=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=3)=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 903127382-Bromo-N-(2-hydroxyethyl)-5-(trifluoromethyl)benzenesulfonamideHCID 90312891HCID 90312891, compound

Product 1

HCID 903141554'-(5-Amino-3-cyanopyrazin-2-yl)-3'-fluoro-N-(2-hydroxyethyl)-4-(trifluoromethyl)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-(2-hydroxyethyl)-5-(trifluoromethyl)benzenesulfonamide. MS (ESI): mass calcd. for C20H15F4N5O3S, 481.08; m/z found, 482.1 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 8.35-8.31 (m, 1H), 8.26 (s, 1H), 8.10-8.05 (m, 1H), 7.91-7.86 (m, 1H), 7.71 (d, J=7.9, 1H), 7.68-7.63 (m, 1H), 7.46 (dd, J=10.9, 1.7, 1H), 7.43-7.36 (m, 3H), 4.75 (t, J=5.4, 1H), 3.40-3.33 (m, 2H), 2.88-2.78 (m, 2H).

Sources & evidence

ORD record
ord-9c1b31f7a8674ddaaf6dad7238c0188e
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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