Hydrochloric Acid → HCID 9884048, compound

Participants

Reaction Steps

A solution of the preceding hydrochloride in water was basified with aqueous sodium hydroxide and the resulting suspension extracted with dichloromethane (3×25 ml). The extracts were dried (MgSO4), evaporated and the residual gum (2.16 g) was combined with 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (1.75 g, 10 mmol) in xylene (50 ml) and the mixture stirred at reflux for 3.5 h. After decanting the mixture whilst hot, the supernatant was allowed to cool and the solid deposited collected and recrystallised twice from ethanol to leave the title compound as buff plates (0.21 g), m.p. 217°-220°; (Found C, 72.09; H, 5.98; N, 16.59. C20H20N4O requires C, 72.27; H, 6.06; N, 16.86%); δH (DMSO-d6) 2.36 (2H, br s, tetrahydropyridinyl CH2), 2.59 (2H, t, J 5.6 Hz, tetrahydropyridinyl CH2), 3.11 (2H, br s, tetrahydropyridinyl CH2), 3.75 (2H, s, ArCH2N), 6.60 (1H, br s, CR=CH), 7.00-7.06 (2H, m, ArH & 5-H), 7.28 (2H, t, J 8.3 Hz, ArH), 7.39 (1H, d, J 2.3 Hz, 2-H), 7.64 (2H, dd, J 8.6, 1.0 Hz, ArH), 8.03 (1H, dd, J 7.8, 1.2 Hz, 4-H), 8.20 (1H, dd, J 4.6, 1.5 Hz, 6-H), 9.60 (1H, s, NH), and 11.47 (1H, br s, 1-H); M/z (CI+, NH3) 333 (M+1)+.

Provenance & Evidence