HCID 90312891, compound → 6-Amino-3-{3-fluoro-2'-[(3-oxopiperazin-1-yl)sulfonyl]-4'-(trifluoromethyl)biphenyl-4-yl}pyrazine-2-carbonitrile

HRID 1524125Notes

Reaction equation

HRID 1524125 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]([N:40]1[CH2:45][CH2:44][NH:43][C:42](=[O:46])[CH2:41]1)(=[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[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:29][C:28]=3[S:37]([N:40]3[CH2:45][CH2:44][NH:43][C:42](=[O:46])[CH2:41]3)(=[O:39])=[O:38])=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 90312891HCID 90312891, compoundHCID 903132434-((2-Bromo-5-(trifluoromethyl)phenyl)sulfonyl)piperazin-2-one

Product 1

HCID 903152426-Amino-3-{3-fluoro-2'-[(3-oxopiperazin-1-yl)sulfonyl]-4'-(trifluoromethyl)biphenyl-4-yl}pyrazine-2-carbonitrile

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-bromo-5-(trifluoromethyl)phenyl)sulfonyl)piperazin-2-one. MS (ESI): mass calcd. for C22H16F4N6O3S, 520.09; m/z found, 520.8 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 8.29 (d, J=1.9, 1H), 8.26 (s, 1H), 8.19 (dd, J=8.2, 1.9, 1H), 8.07-8.01 (m, 1H), 7.77 (d, J=7.9, 1H), 7.70-7.64 (m, 1H), 7.49 (dd, J=10.8, 1.7, 1H), 7.44-7.36 (m, 3H), 3.39 (s, 2H), 3.07-2.96 (m, 4H).

Sources & evidence

ORD record
ord-1b328a83f0694fc8ad245b0597c727a4
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…