Potassium Carbonate → 2-(4-(isoxazol-5-yl)benzyl)-8-chloro-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224271Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[N:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[O:37][N:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>CN(C=O)C.O>[O:37]1[C:33]([C:30]2[CH:31]=[CH:32][C:27]([CH2:26][N:16]3[C:15](=[O:18])[N:4]4[N:5]=[CH:6][C:7]([C:8]5[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=5)=[C:2]([Cl:1])[C:3]4=[N:17]3)=[CH:28][CH:29]=2)=[CH:34][CH:35]=[N:36]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 8-chloro-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (300 mg, 1.07 mmol), prepared as described in Example 354, in DMF (5 mL) was added K2CO3 (180 mg, 1.3 mmol) followed by 5-(4-(bromomethyl)phenyl)isoxazole (305 mg, 1.28 mmol), prepared as described in Example 250A. The reaction mixture was stirred at 70° C. for 2 h. The reaction mixture was cooled to RT, diluted with water (25 mL) and a precipitate formed. The solid was collected by filtration. The solid was washed with water (2×25 mL) followed by hexanes (20 mL). The solid was dried in a vacuum oven at 40° C. The title compound 2-(4-(isoxazol-5-yl)benzyl)-8-chloro-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (450 mg, 96%) was obtained as a yellow solid. HPLC: 3.50 min; M+H=438.

Workup

customprepared
temperatureThe reaction mixture was cooled to RT
customa precipitate formed
filtrationThe solid was collected by filtration
washThe solid was washed with water (2×25 mL)
customThe solid was dried in a vacuum oven at 40° C

Sources & evidence

ORD record: ord-07b5f321272c4c7dab6923f673d3a74d
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

Loading…