Pyridine → n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-(4-{2-[(phenylsulfonyl)amino]phenyl}piperazinyl)ethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide

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Following the procedure for the synthesis of Preparation III, tert-butyl 3-{N-[(1R)-1-[(4-chlorophenyl)methyl]-2-oxo-2-(4-{2-[(phenylsulfonyl)-amino]phenyl}piperazinyl)ethyl]carbamoyl}(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate was prepared from tert-butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Preparation IX) (771 mg, 1.247 mmol), pyridine (110 μl, 1.4 mmol) and benzenesulfonyl chloride (160 μl, 1.3 mmol) (Aldrich). The crude was purified by flash chromatography (SiO2, 10% EtOAc in CH2Cl2) to afford 330 mg of the desired compound. MS (ESI, pos. ion) m/z: 758 (M+H), (ESI, neg. ion) m/z: 756 (M−H). Calc'd for C40H44ClN5O6S: 758.33. Anal. Calcd for C40H44ClN5O6S-0.5 C4H8O2: C, 62.87; H, 6.03; N, 8.73; Cl, 4.42. Found C, 62.49; H, 6.03; N, 8.52.

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