Hydrazine hydrate (1:1) → HCID 70007339, compound

Participants

Reaction Steps

Hydrazine monohydrate (5.14 mmol, 0.26 mL) was added to a solution of 7-[(E)-3-Dimethylamino-allanoyl]-6-(4-fluoro-phenyl)-3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 159) (0.257 mmol, 0.097 g) in 10 mL THF at rt. The reaction mixture was stirred for 42 h. The reaction mixture was evaporated to dryness. The residue was taken up in 2N HCl and extracted with EtOAc several times. The combined organic layers was dried over anhydrous MgSO4 and concentrated to give a yellow oil which was purified by flash silica gel chromatography eluting with a gradient of 0-3% MeOH in CHCl3 to give 0.020 g (23%) of a yellow solid: mp=173-175° C.; 1H NMR (DMSO-d6) δ 3.45-3.52 (m, 2H), 4.03-4.08 (m, 2H), 5.64 (br s, 1H), 7.23 (t, 1H, J=6.0 Hz), 7.32 (t, 2H, J=9.0 Hz), 7.38-7.55 (m, 3), 7.88 (d, 1H, J=6.0 Hz), 8.36-8.43 (m, 2H), 12.67 (br s, 1H); HRMS calcd. for C20H15N4OF (M+) 346.1221, found (M+) 346.1225; Anal. for (C20H15N4OF.1.0MeOH) C, H, N.

Provenance & Evidence