7-(Benzyloxy)-4-chloro-6-methoxyquinazoline → HCID 69935072, compound

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Reaction Conditions

Reaction Steps

A solution of 3-amino-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (3.0 g, 10.7 mmol) in i-PrOH (100 mL) was treated with 4-chloro-6-(methyloxy)-7-[(phenylmethyl)oxy]quinazoline (3.2 g, 10.7 mmol, prepared according to J. Med. Chem. (1999) 42 5369) and stirred at 80° C. for 2 hours before being concentrated. The residue was washed with petroleum ether and dried to give N-methyl-3-({6-(methyloxy)-7-[(phenylmethyl)oxy]-4-quinazolinyl}amino)-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (4.2 g, 72%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.42 (br. s., 1 H), 8.75 (s, 1 H), 8.20 (s, 1 H), 7.80-7.84 (m, 2 H), 7.49-7.57 (m, 4 H), 7.35-7.49 (m, 4 H), 5.34 (s, 2 H), 4.91 (q, J=8.82 Hz, 2 H), 3.99 (s, 3 H), 2.45 (d, J=5.07 Hz, 3 H). MS (m/z) 549.1 (M+H+).

Provenance & Evidence