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

HRID 2238013Notes

Reaction equation

HRID 2238013 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.[OH:19][CH2:20][C:21]([NH:24][S:25]([C:28]1[CH:29]=[N:30][CH:31]=[C:32](Br)[CH:33]=1)(=[O:27])=[O:26])([CH3:23])[CH3:22]>>[OH:19][CH2:20][C:21]([NH:24][S:25]([C:28]1[CH:29]=[N:30][CH:31]=[C:32]([C:18]#[C:17][C:16]2[CH:15]=[N:14][N:11]3[CH:12]=[CH:13][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[N:9][C:10]=23)[CH:33]=1)(=[O:27])=[O:26])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 602093435-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamideHCID 866080485-(4-Chloro-phenyl)-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670004045-[5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

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-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (77 mg, 0.25 mmol) according to general procedure II. Obtained as a yellow solid (74 mg, 62%). MS (ISP) 482.0 [(M+H)+]; mp 185-186° C.

Sources & evidence

ORD record
ord-6162f02c3c514ad39f6a00a4e27326d8
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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