5-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-2-methoxybenzenesulfonamide → 5-[5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-benzenesulfonamide

HRID 269151Notes

Reaction equation

HRID 269151 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[N:14]=[CH:15][C:16]([C:17]#[CH:18])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.Br[C:20]1[CH:21]=[CH:22][C:23]([O:35][CH3:36])=[C:24]([S:26]([NH:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32])(=[O:28])=[O:27])[CH:25]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[N:14]=[CH:15][C:16]([C:17]#[C:18][C:20]4[CH:21]=[CH:22][C:23]([O:35][CH3:36])=[C:24]([S:26]([NH:29][C:30]([CH3:33])([CH3:34])[CH2:31][OH:32])(=[O:28])=[O:27])[CH:25]=4)=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 275180375-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-2-methoxybenzenesulfonamideHCID 866080485-(4-Chloro-phenyl)-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 118516175-[5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-benzenesulfonamide

Procedure

The title compound was prepared from 5-(4-chloro-phenyl)-3-ethynyl-pyrazolo[1,5-a]pyrimidine (example C.6) (63 mg, 0.25 mmol) and 5-bromo-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-benzenesulfonamide (85 mg, 0.25 mmol) according to general procedure II. Obtained as a yellow solid (52 mg, 41%). MS (ISP) 511.1 [(M+H)+]; mp 264-266° C.

Sources & evidence

ORD record
ord-a24cba9324084ae1a58e385e0b161345
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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