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

HRID 558876Notes

Reaction equation

HRID 558876 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([F:16])[F:15])[N:11]3[N:17]=[CH:18][C:19]([C:20]#[CH:21])=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:22].[CH3:23][N:24]([CH3:37])[CH2:25][CH2:26][NH:27][S:28]([C:31]1[S:32][C:33](Br)=[CH:34][CH:35]=1)(=[O:30])=[O:29]>>[CH3:23][N:24]([CH3:37])[CH2:25][CH2:26][NH:27][S:28]([C:31]1[S:32][C:33]([C:21]#[C:20][C:19]2[CH:18]=[N:17][N:11]3[C:12]([CH:14]([F:15])[F:16])=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:22])[CH:4]=4)=[N:9][C:10]=23)=[CH:34][CH:35]=1)(=[O:30])=[O:29]

Participants

3

Reactant 2

HCID 87167995-bromo-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamideHCID 866080845-(4-Chloro-3-methyl-phenyl)-7-difluoromethyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670007525-[5-(4-Chloro-3-methyl-phenyl)-7-difluoromethyl-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)-7-difluoromethyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine (example C.16) (159 mg, 0.5 mmol) and 5-bromo-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, 73%). MS (ISN) 548.1 [(M−H)−]; mp 149° C.

Sources & evidence

ORD record
ord-1605d8e16ec441d2af604230290a6eca
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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