2-bromo-N-(1,3-dihydroxy-2-methylpropan-2-yl)benzenesulfonamide → 4'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-[2-hydroxy-1-(hydroxymethyl)-1-methylethyl]biphenyl-2-sulfonamide

HRID 1523868Notes

Reaction equation

HRID 1523868 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[CH:18]=[N: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]([NH:34][C:35]([CH3:40])([CH2:38][OH:39])[CH2:36][OH:37])(=[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[C:26]([S:31]([NH:34][C:35]([CH2:38][OH:39])([CH3:40])[CH2:36][OH:37])(=[O:32])=[O:33])=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:7][C:2]=2[F:1])=[CH:18][N:19]=1

Participants

3

Reactant 2

HCID 819651352-bromo-N-(1,3-dihydroxy-2-methylpropan-2-yl)benzenesulfonamideHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 903133654'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-[2-hydroxy-1-(hydroxymethyl)-1-methylethyl]biphenyl-2-sulfonamide

Procedure

The title compound was prepared using methods analogous to those described in Example 376 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine and 2-bromo-N-(1,3-dihydroxy-2-methylpropan-2-yl)benzenesulfonamide. MS (ESI): mass calcd. for C20H21FN4O4S, 432.13; m/z found, 433.1 [M+H]+.

Sources & evidence

ORD record
ord-37824f4147d64b61b6b89ec31b19ae11
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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