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

HRID 269314Notes

Reaction equation

HRID 269314 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].[CH3:24][N:25]([CH3:38])[CH2:26][CH2:27][NH:28][S:29]([C:32]1[S:33][C:34](Br)=[CH:35][CH:36]=1)(=[O:31])=[O:30]>>[CH3:24][N:25]([CH3:38])[CH2:26][CH2:27][NH:28][S:29]([C:32]1[S:33][C:34]([C:22]#[C:21][C:20]2[CH:19]=[N:18][N:11]3[C:12]([C:14]([F:15])([F:17])[F:16])=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:23])[CH:4]=4)=[N:9][C:10]=23)=[CH:35][CH:36]=1)(=[O:31])=[O:30]

Participants

3

Reactant 2

HCID 87167995-bromo-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamideHCID 866080535-(4-Chloro-3-methyl-phenyl)-3-ethynyl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670007245-[5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiophene-2-sulfonic acid (2-dimethylamino-ethyl)-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.11) (168 mg, 0.5 mmol) and 5-bomo-thiophene-2-sulfonic acid (2-dimethylamino-ethyl)-amide (example B.49) (157 mg, 0.5 mmol) according to general procedure II. Obtained as a yellow solid (200 mg, 70%). MS (ISN) 566.2 [(M−H)−]; mp 179° C.

Sources & evidence

ORD record
ord-560f8ac568e44e14a04790d673711d37
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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