5-Bromo-N-[2-(4-pyridinyl)ethyl]-2-thiophenesulfonamide → 5-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiophene-2-sulfonic acid (2-pyridin-4-yl-ethyl)-amide

HRID 2238237Notes

Reaction equation

HRID 2238237 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][C:19]([C:20]#[CH:21])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH:30][S:31]([C:34]2[S:35][C:36](Br)=[CH:37][CH:38]=2)(=[O:33])=[O:32])=[CH:24][CH:23]=1>>[N:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][NH:30][S:31]([C:34]2[S:35][C:36]([C:21]#[C:20][C:19]3[CH:18]=[N:17][N:11]4[C:12]([CH:14]5[CH2:16][CH2:15]5)=[CH:13][C:8]([C:5]5[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=5)=[N:9][C:10]=34)=[CH:37][CH:38]=2)(=[O:33])=[O:32])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 613923805-Bromo-N-[2-(4-pyridinyl)ethyl]-2-thiophenesulfonamideHCID 866079965-(4-Chloro-phenyl)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670001445-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-thiophene-2-sulfonic acid (2-pyridin-4-yl-ethyl)-amide

Procedure

The title compound was prepared from 5-(4-chloro-phenyl)-7-cyclopropyl-3-ethynyl-pyrazolo[1,5-a]pyrimidine (example C.5) (147 mg, 0.5 mmol) and 5-bromo-thiophene-2-sulfonic acid (2-pyridin-4-yl-ethyl)-amide (example B.60) (174 mg, 0.5 mmol) according to general procedure II. Obtained as a yellow solid (112 mg, 40%). MS (ISP) 560.2 [(M+H)+]; mp 172-174° C.

Sources & evidence

ORD record
ord-c85f206fa6d94851a5501352d563084e
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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