5-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-2-methoxybenzenesulfonamide → 5-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-benzenesulfonamide

HRID 269145Notes

Reaction equation

HRID 269145 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][C:19]([C:20]#[CH:21])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.Br[C:23]1[CH:24]=[CH:25][C:26]([O:38][CH3:39])=[C:27]([S:29]([NH:32][C:33]([CH3:37])([CH3:36])[CH2:34][OH:35])(=[O:31])=[O:30])[CH:28]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][C:19]([C:20]#[C:21][C:23]4[CH:24]=[CH:25][C:26]([O:38][CH3:39])=[C:27]([S:29]([NH:32][C:33]([CH3:36])([CH3:37])[CH2:34][OH:35])(=[O:31])=[O:30])[CH:28]=4)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 275180375-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-2-methoxybenzenesulfonamideHCID 866079965-(4-Chloro-phenyl)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 118516195-[5-(4-Chloro-phenyl)-7-cyclopropyl-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)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine (example C.5) (73 mg, 0.25 mmol) and 5-bromo-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-benzenesulfonamide (85 mg, 0.25 mmol) (Example B.7) according to general procedure II. Obtained as a yellow solid (38 mg, 28%). MS (ISP) 551.3[(M+H)+]; mp 253-256° C.

Sources & evidence

ORD record
ord-dec3b5ac801f4183a03bdb0a90408815
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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