2-Bromobenzonitrile → 2-[4-Hydroxy-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]benzonitrile

HRID 1675013Notes

Reaction equation

HRID 1675013 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.Br[C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>>[OH:18][C:15]1([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[C:24]#[N:25])[CH2:16][CH2:17][N:12]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([C:2]([F:1])([F:19])[F:20])=[N:4][N:5]=3)[N:8]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 162722-BromobenzonitrileHCID 595783691-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-one

Product 1

HCID 591497412-[4-Hydroxy-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]benzonitrileYield 24%

Procedure

A mixture of 1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-one and 2-bromobenzonitrile was allowed to react by the method of Example 315 to give 2-[4-hydroxy-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]benzonitrile in 24% yield.

Workup

  1. customto react by the method of Example 315

Sources & evidence

ORD record
ord-46bbdb183b1d47338211483c25f60f0c
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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