[NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]2=[N:7][CH:8]=1)[NH2:2].[O:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[OH-].[Na+]>CO.C(Cl)Cl>[O:22]1[CH2:27][CH2:26][CH:25]([C:28]2[N:4]3[C:5]4[CH:11]=[CH:10][NH:9][C:6]=4[N:7]=[CH:8][C:3]3=[N:1][N:2]=2)[CH2:24][CH2:23]1
To a solution of 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.100 g, 0.330 mmol, Preparation #9) in MeOH (2 mL) was added tetrahydro-2H-pyran-4-carbaldehyde (0.038 g, 0.330 mmol, J&W PharmLab) in DCM (1 mL). The reaction mixture was stirred at ambient temperature for about 2 h before iodobenzene diacetate (0.106 g, 0.330 mmol) was added. The reaction mixture was stirred at ambient temperature for about 15 min before it was concentrated to constant weight. To the residue was added MeOH (2 mL) followed by aqueous NaOH (2 N, 0.330 mL, 0.659 mmol). The reaction mixture was heated at about 60° C. for about 1 h. The crude reaction mixture was purified by RP-HPLC (Table 2, Method f). The combined product-containing fractions were concentrated under reduced pressure to remove MeCN and then lyophilized to afford 1-(tetrahydro-2H-pyran-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine as a white solid (0.028 g, 35%): LC/MS (Table 2, Method a) Rt=1.25 min; MS m/z: 244 (M+H)+.
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