Chlorosuccinimide → HCID 69520162, compound

Participants

Reaction Steps

To a solution of N-[4-{5-[(1R)-1-amino-1-methyl-2-phenylethyl]-1,3-oxazol-2-yl}-6-({[(1S,25)-2-methylcyclopropyl]methyl}amino)pyridin-2-yl]-N-methylmethanesulfonamide (0.009 g, 0.015 mmol) in 0.3 mL CH2Cl2 was added 0.09 mL of a 0.15M stock solution of NCS in CH2Cl2. After 15 h, a further 0.10 mL CH2Cl2 and 0.1 mL 0.15 M stock solution of NCS in CH2Cl2 were added. After 24 h, the reaction was concentrated, redissolved in DMF and purified by preparative HPLC to afford N-[4-{5-[(1R)-1-amino-1-methyl-2-phenylethyl]-1,3-oxazol-2-yl}-3-chloro-6-({[(1S,2S)-2-methylcyclopropyl]methyl}amino)pyridin-2-yl]-N-methylmethanesulfonamide as a yellow solid. 1H NMR (400 MHz, d4-MeOH) δ 7.30-7.29 (m, 3H), 7.24 (s, 1H), 7.04-7.02 (m, 3H), 3.47 (d, J=13.3 Hz, 1H), 3.28 (s, 3H), 3.26-3.20 (m, 5H), 1.71 (s, 3H), 1.06 (d, J=5.9 Hz, 3H), 0.85 (m, 1H), 0.71 (m, 1H), 0.43 (m, 1H), 0.27 (m, 1H). LCMS (M+H)=505 (chlorine pattern).

Provenance & Evidence