2-Chloro-1,3-thiazole-5-sulfonamide → 2-[5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiazole-5-sulfonic acid amide

HRID 269179Notes

Reaction equation

HRID 269179 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:21]#[CH:22])=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:23].Cl[C:25]1[S:26][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:28][N:29]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:17])[F:16])[N:11]3[N:18]=[CH:19][C:20]([C:21]#[C:22][C:25]4[S:26][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:28][N:29]=4)=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:23]

Participants

3

Reactant 2

HCID 220195182-Chloro-1,3-thiazole-5-sulfonamideHCID 866080535-(4-Chloro-3-methyl-phenyl)-3-ethynyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670013582-[5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiazole-5-sulfonic acid amide

Procedure

The title compound was prepared from 5-(4-chloro-3-methyl-phenyl)-3-ethynyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (example C.1) (336 mg, 1.0 mmol) and 2-chloro-thiazole-5-sulfonamide (199 mg, 1.0 mmol) according to general procedure II. Obtained as a yellow solid (209 mg, 42%). MS (ISN) 496.0 [(M−H)−]; mp 123° C.

Sources & evidence

ORD record
ord-d24c0596c25d41de8935730d0d343f69
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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