Hydrochloric Acid → HCID 131723851, compound

Participants

Reaction Steps

A solution of 1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-7-carbaldehyde (Example 45, 0.050 g, 0.234 mmol) and MeONH2. HCl (0.020 g, 0.242 mmol) in EtOH (5 mL) and pyridine (5 mL) was refluxed for 20 h. The reaction mixture was then evaporated to dryness and the residue was taken up in H2O and extracted with EtOAc several times. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash silica gel chromatography eluting with a gradient of 0-1% MeOH in CHCl3 to give 0.036 g (63%) of the (E) and 0.013 g (23%) of the (Z) isomers. (Z) isomer: 1H NMR (DMSO-d6) δ 3.54-3.58 (m, 2H), 3.96 (s, 3H), 4.43 (bs, 2H), 7.27 (t, 1H, J=9.0 Hz), 7.89-7.92 (m, 2H), 8.14 (d, 1H, J=9.0 Hz), 8.21 (s, 1H), 8.35-8.39 (m, 1H). HRMS calcd for C13H13N3O2 (M+) 243.1008, found 243.1020. Anal. (C13H13N3O2.0.1 H2O.0.1 EtOAc) C, H, N. (E) isomer: 1H NMR (DMSO-d6) δ 3.55 (bs, 2H), 3.87 (s, 3H), 4.37 (bs, 2H), 7.27 (t, 1H, J=7.5 Hz), 7.75 (s, 1H), 7.91 (d, 1H, J=7.5 Hz), 8.24 (d, 1H, J=7.5 Hz), 8.34-8.38 (m, 2H). HRMS calcd. for C13H13N3O2 (M+) 243.1008, found 243.1016. Anal. (C13H13N3O2.0.25 H2O) C, H, N.

Provenance & Evidence