Cl.[Cl:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][NH:8][CH2:7][CH2:6][C:5]=2[N:4]=1.Cl[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:26][CH2:25][CH2:24]2)[CH2:19][CH2:18]1)=[O:16].C([O-])([O-])=O.[K+].[K+]>CC#N>[NH4+:4].[OH-:16].[Cl:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][N:8]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[CH2:7][CH2:6][C:5]=2[N:4]=1
A mixture of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (80 mg, 0.38 mmol), 1-(chloroacetyl)-4-cyclobutylpiperazine (82 mg, 0.38 mmol), K2CO3 (262 mg, 1.9 mmol) and KI (7 mg, 0.04 mmol) in CH3CN (15 mL) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (10 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (2×10 mL). The combined extracts are dried and evaporated. The resulting oil is purified by PTLC with 100:5:0.5 DCM:MeOH:NH4OH to give the title compound as a white solid; MS (M+1): 349.2; 1H NMR (δ, CDCl3): 7.27 (d, 1H), 7.09 (d, 1H), 3.59-3.67 (m, 6H), 3.38 (s, 2H), 3.01 (t, 2H), 2.87 (t, 2H), 2.64-2.73 (m, 1H), 2.28 (q, 4H), 1.64-2.06 (m, 6H).
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