(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide → (R)-4'-(5-Amino-1,3,4-thiadiazol-2-yl)-3'-fluoro-N-(1-hydroxypropan-2-yl)-[1,1'-biphenyl]-2-sulfonamide

HRID 1523949Notes

Reaction equation

HRID 1523949 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@H:34]([CH3:37])[CH2:35][OH:36])(=[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@H:34]([CH3:37])[CH2:35][OH:36])(=[O:32])=[O:31])=[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 79027397(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamideHCID 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 90313803(R)-4'-(5-Amino-1,3,4-thiadiazol-2-yl)-3'-fluoro-N-(1-hydroxypropan-2-yl)-[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 (R)-2-bromo-N-(1-hydroxypropan-2-yl)benzene-sulfonamide. MS (ESI): mass calcd. for C17H17FN4O3S2, 408.07; m/z found, 409.1 [M+H]+. 1H NMR (300 MHz, CD3OD) δ 8.15-8.12 (m, 2H), 7.68 (m, 1H), 7.61 (m, 1H), 7.44-7.38 (m, 3H), 3.42-3.38 (m, 1H), 3.30-3.25 (m, 1H), 3.22-3.18 (m, 1H), 1.02 (d, J=6.6, 3H).

Sources & evidence

ORD record
ord-bb7485b380a148c08059b43071b97126
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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