4-((2-Bromophenyl)sulfonyl)piperazin-2-one → 3-Amino-6-{3-fluoro-2'-[(3-oxopiperazin-1-yl)sulfonyl]biphenyl-4-yl}pyrazine-2-carbonitrile
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)(=[O:10])=[O:9].[NH2:18][C:19]1[C:20]([C:41]#[N:42])=[N:21][C:22]([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:26]=2[F:40])=[CH:23][N:24]=1>>[NH2:18][C:19]1[C:20]([C:41]#[N:42])=[N:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]([N:11]3[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]3)(=[O:10])=[O:9])=[CH:27][C:26]=2[F:40])=[CH:23][N:24]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using 4-((2-bromophenyl)sulfonyl)piperazin-2-one 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 C21H17FN6O3S, 452.11; m/z found, 453.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.65 (d, J=2.1, 1H), 8.05 (dd, J=8.1, 1.3, 1H), 7.85 (m, 1H), 7.65 (m, 1H), 7.55 (m, 1H), 7.36 (dd, J=7.6, 1.3, 1H), 7.26-7.17 (m, 2H), 3.29 (s, 2H), 3.04 (s, 4H).
Sources & evidence
- ORD record
- ord-214b3676de0a49eda589b17ad2b8de81
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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