反应详情

(Scheme C). A mixture of compound 121 (46 mg, 0.11 mmol), 5-[2-(dimethylamino)ethoxy]indole-2-carboxylic acid hydrochloride (37 mg, 0.13 mmol) and EDCI (83 mg, 0.44 mmol) in DMA (3 mL) was stirred under a N2 atmosphere for 4 h. The mixture was then partitioned between CH2Cl2 and cold (0° C.) 5% aqueous KHCO3. The aqueous portion was extracted with cold CH2Cl2 (×4) and the combined extracts were washed with H2O (×2), brine (×2), dried and evaporated. The residue was dissolved in CH2Cl2/MeOH and the solvents were evaporated under reduced pressure until precipitation began. The precipitate was filtered off and washed with MeOH to give 35 (14 mg, 21%): mp 205-210° C.; 1H NMR [(CD3)2SO] δ 11.73 (s, 1H), 9.30 (s, 1H), 8.85 (d, J=1.6 Hz, 1H), 8.43 (d, J=8.9 Hz, 0.1H), 8.03 (dd, J=8.9, 1.6 Hz, 1H), 7.92 (t, J=5.4 Hz, 1H), 7.41 (d, J=8.9 Hz, 1H), 7.22 (d, J=1.4 Hz, 1H), 7.21 (d, J=2.3 Hz, 1H), 6.94 (dd, J=8.9, 2.4 Hz, 1H), 4.97 (t, J=10.3, Hz, 1H), 4.74 (dd, J=10.9, 2.3 Hz, 1H), 4.68-4.61 (m, 2H), 4.19-4.09 (m, 2H), 4.07 (t, J=5.9 Hz, 2H), 3.43-3.35 (m, 21H), 2.88 (q, J=5.8 Hz, 21H), 2.66 (t J=5.8 Hz, 2H), 224 (s, 6H). HRMS (FAB) calcd. for C28H3035ClN5O7S (MH+) m/z 616.1633, found 616.1630.

1. customThe mixture was then partitioned between CH2Cl2 and cold (0° C.) 5% aqueous KHCO3
2. extractionThe aqueous portion was extracted with cold CH2Cl2 (×4)
3. washthe combined extracts were washed with H2O (×2), brine (×2)
4. customdried
5. customevaporated
6. dissolutionThe residue was dissolved in CH2Cl2/MeOH
7. customthe solvents were evaporated under reduced pressure until precipitation
8. filtrationThe precipitate was filtered off
9. washwashed with MeOH