Potassium Carbonate → HCID 58772593, compound

HRID 2250354Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.Cl[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][C:5]2[N:6]([C:8](=[O:11])[N:9]([CH2:20][C:21]3[CH:26]=[N:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=3)[N:10]=2)[N:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 6-chloro-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (843 mg, 3 mmol), 5-chloromethyl-2-(trifluoromethyl)pyridine (704 mg, 3.6 mmol) and solid K2CO3 (830 mg, 6 mmol) in anhydrous DMF (10 mL) was stirred at 70° C. for 20 min. Analysis by HPLC/MS indicated the reaction was complete. After cooling to room temperature, the reaction was diluted with water and extracted with EtOAc (40 mL×3). The combined EtOAc extracts were washed with saturated aqueous NaCl, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by trituration with CH2Cl2-hexanes to afford 1.10 g (84%) of the title compound as a yellow solid. LC/MS (method A): retention time=3.50 min, (M+H)+=440.

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc (40 mL×3)
washThe combined EtOAc extracts were washed with saturated aqueous NaCl
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude product was purified by trituration with CH2Cl2-hexanes

Sources & evidence

ORD record: ord-028a993d0d124946bcc09fa15f1b87b5
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317012B2

Reaction notes

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