Chloroacetyl chloride → HCID 66610585, compound

Participants

Reaction Steps

A mixture of 2-(((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)amino)ethanol (Example 225, Step 1; 0.118 g, 0.189 mmol), chloroacetyl chloride (0.023 mL, 0.284 mmol) and triethylamine (0.040 mL, 0.284 mmol) in THF (1 mL) was stirred at ambient temperature for 2 h. 2 M K2CO3 (0.2 mL, aq.) and MeOH (1 mL) were added. After 1 h, water was added to the mixture and it was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give N-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-2-chloro-N-(2-hydroxyethyl)acetamide (0.110 g, 0.157 mmol, 83% yield). m/z (ESI, +ve ion) 699.2 (M+H)+.

Provenance & Evidence