[NH2:1][C:2]12[CH2:9][C:6]([C:10]([O:12][CH3:13])=[O:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.[CH3:14][C:15]1[N:20]=[C:19]([C:21](O)=[O:22])[CH:18]=[N:17][CH:16]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O>C(Cl)Cl>[CH3:14][C:15]1[N:20]=[C:19]([C:21]([NH:1][C:2]23[CH2:9][C:6]([C:10]([O:12][CH3:13])=[O:11])([CH2:7][CH2:8]2)[CH2:5][CH2:4][CH2:3]3)=[O:22])[CH:18]=[N:17][CH:16]=1To a solution of methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate (0.98 g, 5.36 mmol) and 6-methylpyrazine-2-carboxylic acid (0.89 g, 6.45 mmol) in DCM (30 mL) and TEA (2 mL) was added PyBOP (3.35 g, 6.44 mmol). After stirring at room temperature overnight, water (30 mL) was added and the mixture was extracted with DCM (3×50 mL). The combined organic layer was washed with Sat. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 1/1) to afford 1.28 g (79%) of methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylate as an off-white solid. ESI-MS m/z: 304 (M+H)+.
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