[Cl:1][C:2]1[C:7](F)=[C:6]([C:9]2[C:10]([NH:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.C([O-])(O)=O.[Na+]>O1CCOCC1>[Cl:1][C:2]1[C:7]2[N:16]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]3[N:11]=[C:12]([NH2:15])[N:13]=[CH:14][C:9]=3[C:6]=2[CH:5]=[CH:4][N:3]=1Compound 193 (3.10 g, 10.1 mmol) was combined with 30 mL of anhydrous 1,4-dioxane. To this was added LiHMDS 1M in THF (30.2 mL, 30.2 mmol) and the solution was heated to 85° C. for 5 hours. The solution was cooled to room temperature and then diluted with ice/sat. NaHCO3. The product was extracted with 15% 2-propanol/DCM and the organics were dried over MgSO4 before being concentrated under vacuum. The residue obtained was purified on CombiFlash column (dry loaded), eluting with a gradient of 2% methanol/DCM to 6% methanol/DCM. Trituration with acetone and ethyl acetate left a light brown solid. Repurification of the supernatants provided additional material. The solids were combined to give compound 194 (1.60 g, 55.2%) as a light brown solid. 1H NMR (500 MHz, DMSO-d6) δ 9.11 (1 H, s), 8.14 (1 H, d, J=4.9 Hz), 7.98 (1 H, d, J=4.9 Hz), 7.07 (2 H, br. s.), 5.90 (1 H, quin, J=8.7 Hz), 2.44-2.49 (2 H, m), 2.04-2.13 (2 H, m), 1.95-2.03 (2 H, m), 1.63-1.73 (2 H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 288.1.
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