Glycolic Acid → N-[(2R)-2-({4-[3-chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)propyl]-2-hydroxy-N-methylacetamide

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Reaction Steps

The N-[(2R)-2-({4-[(3-chloro-4-hydroxyphenyl)amino]quinazolin-5-yl}oxy)propyl]-2-hydroxy-N-methylacetamide starting material was prepared by reacting 2-chloro-4-({5-[(1R)-1-methyl-2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol with and glycolic acid using an analogous procedure to that described in Example 3 for the preparation of 2-hydroxy-N-[2-({4-[4-hydroxy-3-methylanilino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide, to give N-[(2R)-2-({4-[3-chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)propyl]-2-hydroxy-N-methylacetamide in 57% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.91 (m, 1H), 2.97 (s, 3H), 3.39 (dd, 1H), 4.04 (d, 2H), 4.16 (m, 1H), 4.39 (m, 1H), 5.08 (m, 1H), 6.98 (d, 1H), 7.27 (m, 2H), 7.47 (dd, 1H), 7.70 (t, 1H), 7.97 (d, 1H), 8.43 (s, 1H), 9.85 (s, 1H), 9.99 (bs, 1H); Mass spectrum MH+ 417.

Provenance & Evidence