C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]([NH:20][CH2:21][CH2:22]O)[N:17]=[N:18][CH:19]=2)=[CH:10][CH:9]=1.C(N(CC)CC)C.C(O)(C)C>ClCCl.CS(C)=O.C(OCC)(=O)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[N:18][N:17]3[CH:22]=[CH:21][N:20]=[C:16]3[CH:15]=2)=[CH:10][CH:9]=1Oxalyl chloride (3.33 mL, 38.1 mmol) was slowly added to a stirred mixture of DMSO (2.70 mL, 38.1 mmol) in Dichloromethane (25 mL) at −78° C. The mixture was stirred at −78° C. for 10 min before 2-{[5-(4-fluorophenyl)pyridazin-3-yl]amino}ethanol (888 mg, 3.81 mmol) in 3.5 mL DMSO was added. The reaction mixture was left to stir at −78° C. for 20 min, treated with triethylamine (5.31 ml, 38.1 mmol), left to stir at −78° C. for 10 min, and allowed to warm to room temp. The mixture was treated with isopropanol (9 mL), diluted with ethyl acetate (200 mL), and washed with 2% sodium hypochlorite (200 mL) and water (200 mL). The aqueous layer was extracted with chloroform:isopropanol (3:1). The combined organics were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to afford the title compound. LRMS (APCI) calc'd for (C12H9FN3) [M+H]+, 214.1. found 214.0.
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