Dimethylamine → HCID 23533341, compound

Participants

Reaction Steps

A solution of 8-bromo-4-chloro-6-methoxy-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide (Reference Example 28a) (0.1512 g, 0.317 mmol) in 100 mL 2.0 M dimethyl amine in tetrahydrofuran was heated at 100° C. in a Parr bomb. The initial pressure was 75-80 psi and then remained at approximately 60 psi. After 18 hours, the reaction was cooled to room temperature, concentrated and dried to afford the crude product as a brown solid. Purification on silica gel using a gradient of 100:0 to 95:5 methylene chloride:methanol afforded the clean product (0.142 g, 92%); 1H NMR (300 MHz, DMSO, d6) δ 10.20 (s, 1H, C(O)NH), 7.90 (d, 1H, Jm=2.7 Hz, ArH5), 7.69 (d, 2H, Jo=9.0 Hz, ArH2′ & H6′), 7.60 (s, 1H, ArH3), 7.41 (d, 1H, Jm=2.7 Hz, ArH7), 7.01 (d, 2H, J=9.0 Hz, ArH3′ & H5′), 3.96 (s, 3H, OCH3), 3.75 (t, 4H, J=4.8 Hz, OCH2CH2N), 3.10 (t, 4H, J=4.8 Hz, OCH2CH2N), 3.08 (s, 6H, N(CH3)2); Mass Spec.: calc. for [C21H19BrClN3O3+H]+ Theor. m/z=485, 487; Obs.=485, 487.

Provenance & Evidence