4-((2-Bromophenyl)sulfonyl)thiomorpholine 1,1-dioxide → 6-Amino-3-{2'-[(1,1-dioxidothiomorpholin-4-yl)sulfonyl]-3-fluorobiphenyl-4-yl}pyrazine-2-carbonitrile
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]([N:36]1[CH2:41][CH2:40][S:39](=[O:43])(=[O:42])[CH2:38][CH2:37]1)(=[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[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[S:33]([N:36]3[CH2:37][CH2:38][S:39](=[O:42])(=[O:43])[CH2:40][CH2:41]3)(=[O:34])=[O:35])=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1Participants
3
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 4-((2-bromophenyl)sulfonyl)thiomorpholine 1,1-dioxide. MS (ESI): mass calcd. for C21H18FN5O4S2, 487.08; m/z found, 488.1 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 8.26 (s, 1H), 8.08 (dd, J=8.0, 1.3, 1H), 7.83-7.77 (m, 1H), 7.73-7.68 (m, 1H), 7.68-7.63 (m, 1H), 7.51 (dd, J=7.6, 1.3, 1H), 7.44 (dd, J=10.9, 1.7, 1H), 7.40 (s, 2H), 7.35 (dd, J=7.9, 1.6, 1H), 3.31-3.23 (m, 4H), 3.11-3.04 (m, 4H).
Sources & evidence
- ORD record
- ord-641b8da150974f31bc4af512a1512547
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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