Hydrochloric Acid → HCID 59515536, compound

HRID 1160218Notes

Reaction equation

Cl[C:2]1[C:3]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.C1C[O:29]CC1.C[Si](C)(C)[O-].[K+].Cl>O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:4]2[C:5](=[O:29])[NH:10][N:9]3[C:8](=[O:11])[NH:6][N:7]=[C:2]3[C:3]=2[C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a r.b. flask was added 6-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (100 mg, 0.256 mmol), prepared as described in Example 1F, THF (5 ml) and potassium trimethylsilanolate (132 mg, 1.026 mmol). The reaction mixture was stirred at 85° C. for 1.5 hrs. After this time, the solution was cooled to RT and the reaction was diluted with water (25 ml). The pH of the solution was adjusted to 4 with 1N HCl. The resultant solution was extracted with EtOAc (3×20 ml). The combined organic layers were washed with water (20 ml), saturated NaCl (20 ml). The organic layers was dried (MgSO4), filtered and concentrated to give the title compound, 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione (90 mg, 95% yield) as yellow solid. MS (M+H)=372.9.

Workup

customprepared
temperatureAfter this time, the solution was cooled to RT
extractionThe resultant solution was extracted with EtOAc (3×20 ml)
washThe combined organic layers were washed with water (20 ml), saturated NaCl (20 ml)
dry with materialThe organic layers was dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-81f3fb0ee84b455aaf2ebfd80c697f23
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816357B2

Reaction notes

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