F[C:2]1[C:3]([NH:9][NH2:10])=NC=C[C:7]=1[CH3:8].[OH2:11].NN.Br[C:15]1[C:20]([F:21])=[C:19]([CH3:22])[CH:18]=[CH:17][N:16]=1.CCN(C(C)C)C(C)C.[CH:32]([OH:35])(C)C>>[F:21][C:20]1[C:15]([N:10]2[C:7]([CH3:8])=[C:2]([C:32]([OH:35])=[O:11])[CH:3]=[N:9]2)=[N:16][CH:17]=[CH:18][C:19]=1[CH3:22]3-Fluoro-2-hydrazinyl-4-methylpyridine: In a microwave vial, a solution of hydrazine monohydrate (0.051 mL, 1.053 mmol), 2-bromo-3-fluoro-4-methylpyridine (200 mg, 1.053 mmol), DIEA (0.551 mL, 3.16 mmol) in isopropanol (2 mL) was heated at 50° C. overnight. Additional hydrazine monohydrate (0.100 mL) was added and the reaction was heated at 100° C. for 30 min, then 120° C. for 30 min in a microwave reactor. Additional hydrazine monohydrate (0.100 mL) was added and the reaction was heated at 120° C. overnight. The volatile organics were removed in vacuo and the residue was washed with CH2Cl2. The resulting solid was filtered to provide the desired product. MS(ESI) m/z: 142.0 (M+H)+.
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