Potassium Carbonate → HCID 59716724, compound

HRID 2224233Notes

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][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=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]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (192 mg, 0.54 mmol), prepared as described in Example 1, K2CO3 (90 mg), and α-bromo-p-toluonitrile (127 mg, 0.645 mmol) in DMF (2 mL) was heated at 75° C. for 1 h. After this time, the solution was concentrated under redcued pressure. The resulting crude product was purified by reverse phase HPLC to provided the title compound, 4-((7,8-bis-(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)methyl)benzonitrile (80 mg) as a yellow solid. MS M+H=472; 1H NMR (CDCl3): δ 8.17 (s, 1H), 7.63 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.3 Hz, 2H), 7.33 (m, 2H), 7.25 (m, 2H), 7.24 (m, 2H), 7.09 (m, 2H), 5.25 (2H).

Workup

concentrationAfter this time, the solution was concentrated under redcued pressure
customThe resulting crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-6a05144c2604442aad1e7d18031f0f0f
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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