[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6](=[O:12])[N:5]3[C@H:13]([CH2:15][N:16]4[CH2:20][CH2:19][C@@H:18]([CH2:21][NH:22]C(=O)C(F)(F)F)[CH2:17]4)[CH2:14][N:3]1[C:4]=23.C(=O)([O-])[O-].[K+].[K+]>CO.O.CO.C(Cl)Cl>[NH2:22][CH2:21][C@@H:18]1[CH2:19][CH2:20][N:16]([CH2:15][C@H:13]2[N:5]3[C:4]4[N:3]([C:2](=[O:1])[CH:11]=[CH:10][C:9]=4[CH:8]=[CH:7][C:6]3=[O:12])[CH2:14]2)[CH2:17]1To a 25 mL round-bottomed flask was added N-[((3S)-1-{[(1R)-4,9-dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl]methyl}-3-pyrrolidinyl)methyl]-2,2,2-trifluoroacetamide (85 mg, 0.214 mmol) in methanol (9 ml) and water (1.00 ml) to give a yellow solution. Potassium carbonate (59.3 mg, 0.429 mmol) was added and the reaction was stirred overnight. LCMS indicated a complete reaction. The reaction was diluted with 20% MeOH/DCM (100 mL), dried over Na2SO4, filtered and concentrated to give the product (60 mg, 0.200 mmol, 93% yield) as an orange solid.
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