HCID 90312891, compound → 4'-(5-Amino-3-cyanopyrazin-2-yl)-N-ethyl-3'-fluoro-4-(trifluoromethyl)-[1,1'-biphenyl]-2-sulfonamide

HRID 1524123Notes

Reaction equation

HRID 1524123 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]([NH:40][CH2:41][CH3:42])(=[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[C:28]([S:37]([NH:40][CH2:41][CH3:42])(=[O:39])=[O:38])=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 90312891HCID 90312891, compoundHCID 903136902-Bromo-N-ethyl-5-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 903138504'-(5-Amino-3-cyanopyrazin-2-yl)-N-ethyl-3'-fluoro-4-(trifluoromethyl)-[1,1'-biphenyl]-2-sulfonamide

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 2-bromo-N-ethyl-5-(trifluoromethyl)benzenesulfonamide. MS (ESI): mass calcd. for C20H15F4N5O2S, 465.09; m/z found, 465.8 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 8.26 (s, 2H), 8.11-8.07 (m, 1H), 7.87-7.81 (m, 1H), 7.72 (d, J=7.9, 1H), 7.69-7.63 (m, 1H), 7.45 (dd, J=10.8, 1.7, 1H), 7.43-7.36 (m, 3H), 2.78 (qd, J=7.2, 5.5, 2H), 0.97 (t, J=7.2, 3H).

Sources & evidence

ORD record
ord-70fc6b49edfc4abe9e57429d658949d2
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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