Potassium Carbonate → 4-((7-(4-Chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)methyl)benzonitrile

HRID 2224246Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[N:15]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (96 mg, 0.3 mmol), prepared as described in Example 244, K2CO3 (82 mg, 0.59 mmol), and α-bromo-p-toluonitrile (70 mg, 0.356 mmol) in DMF (1 mL) was heated at 65° C. for 2.5 h. Using a similar procedure as described in Example 247, the crude product was obtained. The crude product was purified by reverse phase HPLC to give the title compound, 4-((7-(4-Chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)methyl)benzonitrile (27 mg) as a yellow solid. HPLC RT: 2.45 min; M+H=439; 1H NMR (CDCl3): δ 8.63 (d, J=6.04 Hz, 2H), 8.21 (s, 1H), 7.63 (d, J=8.2 Hz, 2H), 7.49 (d, J=8.2 Hz, 2H), 7.33 (m, 2H), 7.21 (m, 2H), 7.08 (m, 2H), 5.25 (2H).

Workup

customthe crude product was obtained
customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-6c5dee68d335430fb312d495541e951e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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