CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=2)[C:14]([NH2:16])=[O:15])O1.Br[C:20]1[N:25]2[CH:26]=[CH:27][N:28]=[C:24]2[C:23]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)=[CH:32][CH:31]=2)=[N:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH3:11].[CH3:42][N:39]1[CH2:40][CH2:41][N:36]([C:33]2[CH:34]=[CH:35][C:30]([NH:29][C:23]3[C:24]4[N:25]([CH:26]=[CH:27][N:28]=4)[C:20]([C:9]4[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=4)[C:14]([NH2:16])=[O:15])=[CH:21][N:22]=3)=[CH:31][CH:32]=2)[CH2:37][CH2:38]1In the same way as described for Compound 127, step 4, using 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinamide (51.6 mg, 0.207 mmol), (5-bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amine (40 mg, 0.103 mol), Pd(PPh3)4 (30 mg, 0.026 mmol) and 1.5M Na2CO3 (0.55 mL), in dioxane (0.46 mL) and DMF (1.01 mL). The residue is chromatographed on silica gel, eluting with DCM followed by 96:4 DCM:NH3 (7M in MeOH) to afford the title compound (4.8 mg, 11%). LCMS: Rt 1.74 min (97%) m/z (APCI) 429; 1H-NMR (400 MHz, d6-DMSO) δ (ppm).2.26 (3H, s), 2.49-2.54 (4H, m), 3.12 (4H, m), 6.97 (2H, d), 7.57 (1H, s), 7.73 (1H, s), 7.75 (1H, br s), 7.91 (2H, d), 8.07 (1H, s), 8.29 (1H, br s), 8.54 (1H, s), 9.03 (1H, s), 9.14 (1H, s), 9.58 (1H, s).
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