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

HRID 269140Notes

Reaction equation

HRID 269140 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[S:35][C:34](Cl)=[N:33][CH:32]=1)(=[O:30])=[O:29])([CH3:26])[CH3:25]>>[OH:22][CH2:23][C:24]([NH:27][S:28]([C:31]1[S:35][C:34]([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)=[N:33][CH:32]=1)(=[O:30])=[O:29])([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 610526512-Chloro-N-(1-hydroxy-2-methylpropan-2-yl)thiazole-5-sulfonamideHCID 866079965-(4-Chloro-phenyl)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670008272-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiazole-5-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) (73 mg, 0.25 mmol) and 2-chloro-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (68 mg, 0.25 mmol) (example B.14) according to general procedure II. Obtained as a yellow solid (60 mg, 45%). MS (ISP) 528.0 [(M+H)+]; mp 204-207° C.

Sources & evidence

ORD record
ord-47f3b50eb7834b5582baf1c78187c584
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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