反应详情

Triethylamine (210 μL, 1.52 mmol) and then thiophosgene (55 μL, 0.72 mmol) were added to a solution of Example 45C (200 mg, 0.55 mol) in dichloromethane (5 mL), and the reaction stirred 1 h at r.t. Organics were washed with 0.5 N HCl and brine, dried (MgSO4), and concentrated. The residue was dissolved in DMF (5 mL). Phenylenediamine (89 mg, 0.82 mmol) was added, and the reaction stirred at 90° C. for 2 h. Mercury(II) oxide was added, and the reaction stirred for 3 h longer before it was concentrated in vacuo. Deprotection was carried out in ethanol (5 mL) with hydrazine (0.2 mL) at r.t. for 1 h. Purification by Prep-HPLC gave 145 mg (46%) of the title compound (TFA salt) as a yellow solid. H1-NMR (MeOD-d4): δ 8.61 (s, 1H), 7.38-7.42 (m, 2H), 7.30-7.34 (m, 2H), 7.23 (s, 1H); 7.02 (d, 1H, J=2.0 Hz), 6.89 (d, 1H, J=2.0 Hz), 4.92 (s, 2H), 4.01 (s, 3H), 3.91 (s, 3H). MS (ES) (M+H) calc'd for C19H19N5O2, 350; found 350.

1. washOrganics were washed with 0.5 N HCl and brine
2. dry with materialdried (MgSO4)
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in DMF (5 mL)
5. stirringthe reaction stirred at 90° C. for 2 h
6. stirringthe reaction stirred for 3 h longer before it
7. concentrationwas concentrated in vacuo
8. waitDeprotection was carried out in ethanol (5 mL) with hydrazine (0.2 mL) at r.t. for 1 h
9. customPurification by Prep-HPLC