Dimethylamine → HCID 44629538, compound

Participants

Reaction Steps

Reaction of N4-(3-bromophenyl)-4,6-quinazolinediamine (10) (1.76 g, 5.58 mmol) with 4-chlorobutanoyl chloride (0.75 mL, 6.70 mmol) and then aqueous dimethylamine according to the general procedure A, with the exception that the first step was performed in dioxane and the second at 50° C. for 24 hours, gave N-[4-(3-bromoanilino)-6-quinazolinyl]-4-(dimethylamino)butanamide (16) (36%) as a white solid, m.p. (MeOH) 180-182° C. 1H NMR [(CD3)2SO] δ 10.23 (s, 1H), 9.87 (s, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.57 (s, 1H), 8.17 (dd, J=1.9, 1.9 Hz, 1H), 7.88-7.84 (m, 2H), 7.77 (d, J=8.9 Hz, 1H), 7.37-7.27 (m, 2H), 2.43 (t, J=7.2 Hz, 2H), 2.29 (t, J=7.2 Hz, 2H), 2.16 (s, 6H), 1.78 (quintet, J=7.2 Hz, 2H). Analysis found: C, 55.46; H, 5.33; N, 15.96. C20H22BrN5O.¼H2O requires: C, 55.50; H, 5.24; N, 16.18.

Provenance & Evidence