Triethylamine → methanesulfonic acid 5-{4-[3-chloro-4-(pyridine-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-oxo-pent-3-enyl ester

Participants

Reaction Steps

In a 250 ml rb flask were placed 1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenyl amino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-hydroxy-pent-2-en-1-one (1.00 g, 1.91 mmol) in THF (80 ml) and to the solution was added triethylamine (0.58 g, 5.74 mmol) (0.80 ml) followed by methanesulfonyl chloride (0.54 g, 4.79 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. THF was evaporated and to the residue was added water and small amount of methyl alcohol, sonicated. The precipitated off-white solid was filtered, washed with methyl alcohol and dried to provide 0.63 g of off-white solid. (55%) 1H-NMR (DMSO-d6) δ 8.601-8.585 (m, 1H), 8.394 (s, 1H), 8.196 (s, 1H), 7.906-7.864 (m, 1H), 7.769 (s, 1H), 7.584-7.564 (d, 1H), 7.523-7.501 (d, 1H), 7.388-7.357 (m, 1H), 7.239-7.216 (d, 1H), 6.765-6.703 (m, 2H), 5.280 (s, 2H), 4.957 (s, 1H), 4.843 (s, 1H), 4.366-4.337 (m, 2H), 3.940-3.860 (m, 2H), 3.255-3.189 (m, 6H), 2.655-2.626 (m, 2H). MS m/e 600.0 (M+H), RT=2.78 min

Provenance & Evidence