To a stirred solution of 3-(trans-3-cyclopropylmethoxytetrahydrofuran-4-ylamino)-6-chloro-1-carboxymethylpyrazinone from step 7 above (50 mg, 0.15 mmol) in DMF (1.0 mL) was added 5-aminomethyl-3-chloro-7-azaindole bis-hydrochloride salt (41 mg, 0.16 mmol) and HOBT (24 mg, 0.16 mmol). The solution was brought to pH 7 by the addition of DIEA (approximately 0.1 mL). EDC (70 mg, 0.24 mmol) was added and the solution was stirred at ambient temperature for 18 h. The reaction was concentrated in vacuo and partitioned between water and EtOAc. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography using 9:1 CH2Cl2:MeOH as eluant. The free base of the title compound was dissolved in MeOH containing 3 equivalents of aqueous HCl and the solution was evaporated in vacuo to give the HCl salt of the title compound as an amorphous solid (45 mg, TLC Rf=0.46, 92:8:0.4 CH2Cl2:MeOH:NH4OH; HPLC RT=8.6 min, method A; M+1 peak at m/z=508, electrospray mass spec).
