2-bromo-N-tert-butylbenzenesulfonamide → 4'-(5-Amino-1,3,4-thiadiazol-2-yl)-N-(tert-butyl)-3'-fluoro-[1,1'-biphenyl]-2-sulfonamide

HRID 1523948Notes

Reaction equation

HRID 1523948 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[S:21][C:20]([NH2:22])=[N:19][N:18]=1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:32])=[O:31]>>[NH2:22][C:20]1[S:21][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:24]3[C:25]([S:30]([NH:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:31])=[O:32])=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:7][C:2]=2[F:1])=[N:18][N:19]=1

Participants

3

Reactant 2

HCID 48250142-bromo-N-tert-butylbenzenesulfonamideHCID 903143255-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 903139544'-(5-Amino-1,3,4-thiadiazol-2-yl)-N-(tert-butyl)-3'-fluoro-[1,1'-biphenyl]-2-sulfonamide

Procedure

The title compound was prepared using analogous conditions to those described in Example 6 utilizing 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-thiadiazol-2-amine and 2-bromo-N-(tert-butyl)benzenesulfonamide. MS (ESI): mass calcd. for C18H19FN4O2S2, 406.09; m/z found, 407.1 [M+H]+. 1H NMR (300 MHz, CD3OD) δ 8.20-8.10 (m, 2H), 7.69-7.56 (m, 2H), 7.46-7.36 (m, 3H), 1.08 (s, 9H).

Sources & evidence

ORD record
ord-854862ee3ca048d09b8f079d385c612f
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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