5-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamide → 5-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 558705Notes

Reaction equation

HRID 558705 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.[OH:22][CH2:23][C:24]([NH:27][S:28]([C:31]1[CH:32]=[N:33][CH:34]=[C:35](Br)[CH:36]=1)(=[O:30])=[O:29])([CH3:26])[CH3:25]>>[OH:22][CH2:23][C:24]([NH:27][S:28]([C:31]1[CH:32]=[N:33][CH:34]=[C:35]([C:21]#[C:20][C:19]2[CH:18]=[N:17][N:11]3[C:12]([CH:14]4[CH2:16][CH2:15]4)=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)=[N:9][C:10]=23)[CH:36]=1)(=[O:30])=[O:29])([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 602093435-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamideHCID 866079965-(4-Chloro-phenyl)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670011075-[5-(4-Chloro-phenyl)-7-cyclopropyl-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)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine (example C.5) (147 mg, 0.5 mmol) and 5-bromo-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (155 mg, 0.5 mmol) (example B.2) according to general procedure II. Obtained as a yellow solid (137 mg, 52%). MS (ISP) 522.2 [(M+H)+]; mp 230-231° C.

Sources & evidence

ORD record
ord-ae1842eb093548019cc6223b0374c981
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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