[C:1]1([C:7]2[N:12]=[N:11][C:10]([N:13]3[CH2:20][CH:19]4[NH:21][CH:15]([CH2:16][CH2:17][CH2:18]4)[CH2:14]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:23][CH3:24].C(N(CC)C(C)C)(C)C.[OH-].[Na+]>CN(C)C=O>[CH2:23]([N:21]1[CH:15]2[CH2:16][CH2:17][CH2:18][CH:19]1[CH2:20][N:13]([C:10]1[N:11]=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=1)[CH2:14]2)[CH3:24]A mixture of 3-(6-phenyl-pyridazin-3-yl)-3,9-diaza-bicyclo[3.3.1]nonane free base (0.20 g, 0.71 mmol), bromoethane (0.059 ml, 0.78 mmol), N,N-diisopropylethylamine (0.18 g, 1.42 mmol) and dimethylformamide (5 ml) was stirred at 80° C. for 2 hours. Aqueous sodium hydroxide (20 ml, 1 M) was added and the mixture was extracted twice with diethylether (2×20 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound as a crystalline solid. LC-ESI-HRMS of [M+H]+ shows 281.1761 Da. Calc. 281.176621 Da, dev. −1.9 ppm.
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