5-bromo-N-(1,3-dihydroxy-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-hydroxymethyl-1-methyl-ethyl)-amide

HRID 2238007Notes

Reaction equation

HRID 2238007 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:28][S:29]([C:32]1[CH:33]=[N:34][CH:35]=[C:36](Br)[CH:37]=1)(=[O:31])=[O:30])([CH2:26][OH:27])[CH3:25]>>[OH:22][CH2:23][C:24]([NH:28][S:29]([C:32]1[CH:33]=[N:34][CH:35]=[C:36]([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:37]=1)(=[O:31])=[O:30])([CH2:26][OH:27])[CH3:25]

Participants

3

Reactant 2

HCID 670009725-bromo-N-(1,3-dihydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamideHCID 866079965-(4-Chloro-phenyl)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670010635-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridine-3-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-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) (73 mg, 0.25 mmol) and 5-bromo-pyridine-3-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (81 mg, 0.25 mmol) (example B.4) according to general procedure II. Obtained as a yellow solid (68 mg, 50%). MS (ISP) 538.0 [(M+H)+]; mp 204-206° C.

Sources & evidence

ORD record
ord-bdea1e7618c94f27ad4697820ac3ac21
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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