5-Bromo-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amide → 5-[7-Difluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amide

HRID 1293991Notes

Reaction equation

HRID 1293991 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]2[C:11]([CH:12]([F:14])[F:13])=[CH:10][C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:8][C:7]=12)#[CH:2].[OH:25][CH2:26][CH2:27][N:28]([CH2:38][CH2:39][OH:40])[S:29]([C:32]1[S:33][C:34](Br)=[CH:35][CH:36]=1)(=[O:31])=[O:30]>>[OH:25][CH2:26][CH2:27][N:28]([CH2:38][CH2:39][OH:40])[S:29]([C:32]1[S:33][C:34]([C:2]#[C:1][C:3]2[CH:4]=[N:5][N:6]3[C:11]([CH:12]([F:14])[F:13])=[CH:10][C:9]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=4)=[N:8][C:7]=23)=[CH:35][CH:36]=1)(=[O:31])=[O:30]

Participants

3

Reactant 2

HCID 612345545-Bromo-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amideHCID 866080813-Ethynyl-7-difluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670012135-[7-Difluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amide

Procedure

The title compound was prepared from 3-ethynyl-7-difluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.15) (169 mg, 0.5 mmol) and 5-bromo-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amide (example B.53) (165 mg, 0.5 mmol) according to general procedure II. Obtained as a yellow solid (210 mg, 72%). MS (ISP) 587.1 [(M+H)+]; mp 174° C.

Sources & evidence

ORD record
ord-08a0d5f1bd5542bd80d60fd2ec491790
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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