5-bromo-N-(1,3-dihydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamide → 5-[7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridine-3-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide

HRID 1293768Notes

Reaction equation

HRID 1293768 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:8][C:7]=12)#[CH:2].[OH:26][CH2:27][C:28]([NH:32][S:33]([C:36]1[CH:37]=[N:38][CH:39]=[C:40](Br)[CH:41]=1)(=[O:35])=[O:34])([CH2:30][OH:31])[CH3:29]>>[OH:26][CH2:27][C:28]([NH:32][S:33]([C:36]1[CH:37]=[N:38][CH:39]=[C:40]([C:2]#[C:1][C:3]2[CH:4]=[N:5][N:6]3[C:11]([C:12]([F:14])([F:13])[F:15])=[CH:10][C:9]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=4)=[N:8][C:7]=23)[CH:41]=1)(=[O:35])=[O:34])([CH2:30][OH:31])[CH3:29]

Participants

3

Reactant 2

HCID 670009725-bromo-N-(1,3-dihydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamideHCID 715397323-Ethynyl-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 118521275-[7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-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 3-ethynyl-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.1) (200 mg, 0.56 mmol) and 5-bromo-pyridine-3-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (example B.4) (165 mg, 0.5 mmol) according to general procedure II. Obtained as a yellow solid (120 mg, 35%). MS (ISP) 600.2 [(M+H)+]; mp 228–231° C.

Sources & evidence

ORD record
ord-e0ec55562d8847289b4505ed2003b5c9
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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