5-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamide → 5-[6-(4-Chloro-phenyl)-8-methyl-imidazo [1,2-a]pyridin-3-ylethynyl]-pyridine-3-sulfonic acid(2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 269289Notes

Reaction equation

HRID 269289 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH3:19])[C:11]3[N:12]([C:14]([C:17]#[CH:18])=[CH:15][N:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.[OH:20][CH2:21][C:22]([NH:25][S:26]([C:29]1[CH:30]=[N:31][CH:32]=[C:33](Br)[CH:34]=1)(=[O:28])=[O:27])([CH3:24])[CH3:23]>>[OH:20][CH2:21][C:22]([NH:25][S:26]([C:29]1[CH:30]=[N:31][CH:32]=[C:33]([C:18]#[C:17][C:14]2[N:12]3[CH:13]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH:9]=[C:10]([CH3:19])[C:11]3=[N:16][CH:15]=2)[CH:34]=1)(=[O:28])=[O:27])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 602093435-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamideHCID 866080946-(4-Chloro-phenyl)-3-ethynyl-8-methyl-imidazo[1,2-a]pyridine

Product 1

HCID 167352685-[6-(4-Chloro-phenyl)-8-methyl-imidazo [1,2-a]pyridin-3-ylethynyl]-pyridine-3-sulfonic acid(2-hydroxy-1,1-dimethyl-ethyl)-amide

Procedure

The title compound was prepared from 6-(4-chloro-phenyl)-3-ethynyl-8-methyl-imidazo[1,2-a]pyridine (example C.21) (270 mg, 1 mmol) and 5-bromo-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (example B.2) (282 mg, 0.9 mmol) according to general procedure II. Obtained as a light yellow solid (180 mg, 35%). MS (ISP) 495.0 [(M+H)+], 497 [(M+2+H)+]; mp 215-217° C.

Sources & evidence

ORD record
ord-6415bc514316492e9c9eb9886001abc7
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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