Dimethylamine → HCID 10298728, compound

Participants

Reaction Conditions

Reaction Steps

An amount of 500 mg (1.09 mmol) of 9-(3-chloro-4-fluoroanilino)-1-[4-(chlorobutyryl)butanoyl]-2,3-dihydro-1H-[1,4]oxazino[3,2-g]quinoline-8-carbonitrile was stirred in N,N-dimethylformamide (4.5 mL), and to this was added sodium iodide (0.163 g, 1.69 mmol), tetrabutylammonium iodide (0.80 g, 0.22 mmol), and dimethylamine solution in tetrahydrofuran 2M (11 mL, 21.8 mmol). The mixture was heated at 45° C. for 4 hours and stirred at room temperature for an additional 16 hours. To this was added ethyl acetate and sodium bicarbonate solution, and after separation of the layers, the organic phase was dried over sodium sulfate and evaporated to obtain the crude product. Purification of the crude product was carried out by flash chromatography (20% acetone in methanol), to give a tan solid (129 mg, 33% yield), m.p. 165° C.; 1H NMR (DMSO-d6) δ 9.78 (bs, 1H), 8.69 (bs, 1H), 8.39 (s, 1H), 7.39 (m, 2H), 7.26 (s, 1H), 7.21 (m, 1H), 4.39 (t, 2H), 3.98 (t, 2H), 2.64 (t, 2H), 2.20 (t, 2H), 2.07 (s, 6H), 1.71 (m, 2H); HRMS (EI) m/z 467.1514 (M+1). Analysis for C24H23ClFN5O2.0.3H2O.0.3C2H5CO2CH3: Found: C, 60.22; H, 5.16; N, 14.12. Calcd: C, 60.56; H, 5.24; N, 14.01.

Provenance & Evidence