Hydrochloric Acid → HCID 69436101, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1,3-difluoro-11-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-2-trimethylsilanyl-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-8-ol (2.2 g, 3.8 mmol) in acetonitrile (100 mL) and add tetrabutylammonium fluoride hydrate (2.0 g, 7.6 mmol) and heat to 70° C. for 4 hours. Cool the reaction to room temperature and partition between water and ethyl acetate. Extract the organic layer with water three times. Dry with sodium sulfate, filter and concentrate in vacuo. Dissolve the residue in methylene chloride (8 mL) and add HCl (2M in ether, 3.8 mL, 7.6 mmol). Add the solution slowly to vigorously stirred ether and collect the precipitate. Dry at 50° C. under vacuum over night to yield 1.9 g (93%) of the title compound as a tan solid. 1H NMR (d6-DMSO) δ10.09 (s, 1H), 10.02 (bs, 1H), 8.36 (d, J=9.2 Hz, 1H), 7.92 (d, J=8.6 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.31 (d, J=2.5 Hz, 1H), 7.22 (dd, J=9.4, 2.7 Hz, 1H), 7.13 (td, J=9.6, 2.3 Hz, 1H), 6.99 (m, 2H), 6.64 (m, 4H), 4.97 (d, J=12.3 Hz, 1H), 4.19 (t, J=5.2 Hz, 2H), 4.07 (d, J=12.3 Hz, 1H), 3.37 (m, 4H), 2.91 (m, 2H), 1.70 (m, 5H), 1.57 (m, 1H). mass spectrum (apci) m/z-502.3 (M−HCl+H). HPLC (5 to 95) Rt (purity at 254 nm)=2.76 min (>99%). Analysis calculated for C31H30ClF2NO3.H2O: C, 66.96; H, 5.80; N, 2.52. Found: C, 67.00; H, 6.20; N, 2.83.

Provenance & Evidence