C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7](Br)[N:6]=1)=[O:4].[CH:18]1([CH2:21][OH:22])[CH2:20][CH2:19]1.[H-].[Na+].[OH-].[K+]>CN(C=O)C.C(O)=O>[CH:18]1([CH2:21][O:22][C:7]2[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[N:9][C:8]=2[N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:20][CH2:19]1A mixture of 0.12 g (0.4 mmol) 6-bromo-5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester, 0.029 g (0.4 mmol) cyclopropyl methanol and 0.018 g (0.41 mmol) NaH (55% suspension in oil) in 2 mL DMF was shaken for an extended period of time. Afterwards, 0.1 mL KOH (5N aq.) was added and the mixture was heated to 45° C. for 1 h. After addition of formic acid the mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The combined product fractions were evaporated to yield 11 mg (10%) of the title compound. m/z (ES+): 278.1 (M+H).
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