4-((2-Bromophenyl)sulfonyl)piperazin-2-one → 4-{[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]sulfonyl}piperazin-2-one

HRID 1523806Notes

Reaction equation

HRID 1523806 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([N:34]1[CH2:39][CH2:38][NH:37][C:36](=[O:40])[CH2:35]1)(=[O:33])=[O:32]>>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31]([N:34]3[CH2:39][CH2:38][NH:37][C:36](=[O:40])[CH2:35]3)(=[O:33])=[O:32])=[CH:7][C:2]=2[F:1])=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 79377174-((2-Bromophenyl)sulfonyl)piperazin-2-oneHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 778443264-{[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]sulfonyl}piperazin-2-one

Procedure

The title compound was prepared in a manner similar to that described in Example 448 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and 4-((2-bromophenyl)sulfonyl)piperazin-2-one. MS (ESI): mass calcd. for C20H18FN5O3S, 427.11; m/z found, 428.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.37 (s, 1H), 8.27 (d, J=1.4, 1H), 8.17-8.13 (m, 1H), 7.98 (m, 1H), 7.77-7.72 (m, 1H), 7.67-7.62 (m, 1H), 7.47-7.43 (m, 1H), 7.34-7.26 (m, 2H), 3.39 (s, 2H), 3.14 (s, 4H).

Sources & evidence

ORD record
ord-2f6986411bef42a7875d6487b5476488
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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