1H-Pyrazole-4-carbonitrile → 1-[2-[4-[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]phenoxy]ethyl]-1H-pyrazole-4-carbonitrile

HRID 1675152Notes

Reaction equation

HRID 1675152 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[CH:19][C:20]4[N:21]([C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=4)[N:22]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[C:30]([C:32]1[CH:33]=[N:34][NH:35][CH:36]=1)#[N:31]>>[F:27][C:26]([F:29])([F:28])[C:23]1[N:21]2[N:22]=[C:17]([N:14]3[CH2:15][CH2:16][N:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:34]5[CH:33]=[C:32]([C:30]#[N:31])[CH:36]=[N:35]5)=[CH:6][CH:7]=4)[CH2:12][CH2:13]3)[CH:18]=[CH:19][C:20]2=[N:25][N:24]=1

Participants

3

Reactant 2

HCID 5644491H-Pyrazole-4-carbonitrileHCID 673403266-[4-[4-(2-Bromoethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 591497801-[2-[4-[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]phenoxy]ethyl]-1H-pyrazole-4-carbonitrileYield 75%

Procedure

Obtained in 75% yield by an analogous method to Example 847, starting from 6-[4-[4-(2-bromoethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine and 4-cyanopyrazole.

Workup

  1. customObtained in 75% yield by an analogous method to Example 847

Sources & evidence

ORD record
ord-0c3eecf337c24b3882eddb9bc66e6b2d
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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