Dimethylamine → HCID 9956151, compound

Participants

Reaction Steps

An amount of the mixture 1-[(2E)-4-chloro-2-butenoyl]-9-(3-chloro-4-fluoroanilino)-2,3-dihydro-1H-[1,4]oxazino[3,2-g]quinoline-8-carbonitrile and 1-[(2E)-4-bromo-2-butenoyl]-9-(3-chloro-4-fluoroanilino)-2,3-dihydro-1H-[1,4]oxazino[3,2-g]quinoline-8-carbonitrile (0.708 g, 1.458 mmol), was dissolved in N,N-dimethylformamide (1.89 mL), and to this was added N,N-diisopropylethylamine (0.303 mL, 1.75 mmol), and 0.875 mL (1.75 mmol) of a 2.0 M solution of dimethylamine in tetrahydrofuran The reaction mixture was stirred for one hour, stored for 16 hours in the refrigerator, and then stirred with saturated sodium bicarbonate solution and brine. The solid was filtered off and washed with acetone to give a beige product (372 mg, 52% yield); m.p. 199-200° C.; 1H NMR (DMSO-d6) δ 9.70 (bs, 1H), 8.52 (s, 1H), 8.44 (bs, 1H), 7.47-7.37 (m, 3H), 7.25-7.23 (m, 1H), 6.86-6.79 (m, 1H), 6.62-6.57 (d, 1H), 4.44 (t, 2H), 4.06 (t, 2H), 3.02 (d, 2H), 2.06 (s, 6H); HRMS (Cl) m/z 466.1440 (M+1). Analysis for C24H21ClFN5O2.1.4H2O: Found: C, 60.48; H, 4.85; N, 14.49; F, 4.02; Cl, 7.52. Calcd: C, 60.28; H, 4.73; N, 14.66; F, 3.98; Cl, 7.32.

Provenance & Evidence