Reaction equation
Br.Cl[C:3]1[CH:4]=[C:5]([CH3:13])[C:6]2[N:7]([C:9]([NH2:12])=[N:10][N:11]=2)[N:8]=1.CN(C=O)C.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20]>O>[CH2:19]([N:21]([CH2:22][CH3:23])[C:3]1[CH:4]=[C:5]([CH3:13])[C:6]2[N:7]([C:9]([NH2:12])=[N:10][N:11]=2)[N:8]=1)[CH3:20]Participants
Procedure
6-Chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.002; 250 mg) was dissolved in abs. DMF (2 ml) and admixed with diethylamine (7 ml). Thereafter, the reaction mixture was placed into a heating block at 80° C. with stirring for 11 days. The solvent was then drawn off and the residue was admixed with a little water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC (met. A), and the clean product fractions were combined, freed of the acetonitrile under reduced pressure, alkalized with saturated potassium carbonate solution and extracted repeatedly with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 100 mg of the title compound were obtained.
Workup
- customwas placed into a heating block at 80° C.
- extractionextracted three times with dichloromethane
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by means of preparative HPLC (
- extractionextracted repeatedly with dichloromethane
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3a65638af6fd48d88d2ea7b7ca94b982
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198272B2
Linked notes
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