[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([N:14]([CH3:23])[C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH:9]=[C:10]([C:11](O)=[O:12])[C:5]2=[N:4][N:3]=1.C(Cl)(=O)C(Cl)=O.[NH3:30].C1COCC1>C1COCC1>[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([N:14]([CH3:23])[C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH:9]=[C:10]([C:11]([NH2:30])=[O:12])[C:5]2=[N:4][N:3]=1To a solution of compound (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid (200 mg, 0.64 mmol) in anhydrous THF (10 mL) was added oxalyl chloride (0.3 mL) dropwise. The reaction mixture was stirred at room temperature for 2 hrs, then 2N NH3/THF (1 mL) solution was added, and stirred for another 2 hrs. The mixture was concentrated in vacuum and the residue was purified by flash column chromatography (silica-gel, DCM: MeOH=20:1) to give product (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxamide (Compound 7) as a yellow solid (180 mg, 90%). 1H NMR (300 MHz, DMSO) δ 8.66 (s, 1H), 8.40 (s, 1H), 7.66 (s, 1H), 7.26˜7.36 (m, 5H), 5.71˜5.74 (q, 1H), 2.90 (s, 3H), 2.59 (s, 3H), 1.61 (d, J=6.9 Hz, 3H). LRMS (M+H+) calcd. 310; found 310.
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