2-bromo-N-(2-hydroxyethyl)benzenesulfonamide → 4'-(5-Amino-6-cyanopyrazin-2-yl)-3'-fluoro-N-(2-hydroxyethyl)biphenyl-2-sulfonamide
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9].[NH2:15][C:16]1[C:17]([C:38]#[N:39])=[N:18][C:19]([C:22]2[CH:27]=[CH:26][C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][C:23]=2[F:37])=[CH:20][N:21]=1>>[NH2:15][C:16]1[N:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:2]3[C:3]([S:8]([NH:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:24][C:23]=2[F:37])=[N:18][C:17]=1[C:38]#[N:39]Participants
3
Procedure
The title compound was prepared in manner similar to that described in Example 88 using 2-bromo-N-(2-hydroxyethyl)benzenesulfonamide and 3-amino-6-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile. MS (ESI): mass calcd. for C19H16FN5O3S, 413.10; m/z found, 414.0 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.81 (d, J=1.8, 1H), 8.17 (dd, J=8.0, 1.4, 1H), 8.02 (m, 1H), 7.64 (m, 1H), 7.56 (m, 1H), 7.40-7.31 (m, 3H), 5.38 (s, 2H), 4.35 (s, 1H), 3.64-3.58 (m, 2H), 2.95-2.87 (m, 2H), 1.64 (t, J=5.2, 1H).
Sources & evidence
- ORD record
- ord-b38003296e214a83a322283f4f49a69f
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
Loading…