Reaction #6940

Reaction equation

Et3N

THF MeOH

5-{4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde

NaBH4

Isopropylsulfonylethyl amine hydrochloride salt

→

title compound

(4-(3-Fluorobenzyloxy)-3-chlorophenyl)-(6-(2-((2-isopropyl-sulphonyl-ethylamino)-methyl)-furan-2-yl)-quinazolin-4-yl)-amine

Conditions

Procedure

The title compound and its hydrochloride salt are prepared according to Procedure D utilizing 5-{4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde (0.317 mmol, 0.15 g), Isopropylsulfonylethyl amine hydrochloride salt (0.475 mmol, 0.105 g) in the presence of Et3N (0.95 mmol, 0.13 mL) and NaBH4 (1.1 mmol, 0.041 g) in THF/MeOH. 1H NMR (DMSO-d6) 11.74 (bs, 1H); 9.90 (bs, 2H); 9.63 (s, 1H); 8.91 (s, 1H); 8.42 (d, 1H); 8.04 (m,1H); 7.95 (d, 1H); 7.81 (d, 1H); 7.47 (m, 1H); 7.37–7.28 (m, 4H); 7.18 (m, 1H); 6.83 (m, 1H); 5.29 (s, 2H); 4.45 (s, 2H); 3.72–3.39 (m, 5H); 1.26 (d, 6H). Electrospray MS 609.

Source