反应详情

Deprotection of 13 (260 mg, 0.72 mmol) as in Example C, and reaction of the product with 6-[2-(dimethylamino)ethoxy]-5-methoxyindole-2-carboxylic acid hydrochloride (230 mg, 0.73 mmol), EDCI.HCl (345 mg, 1.80 mmol) and DMA (3 mL) at 20° C. for 3 h gave a solid. This was shaken with dilute KHCO3 and the resulting gelatinous solid was collected and chromatographed on alumina-90. Elution with EtOAc/MeOH (10:1) provided the crude product which was recrystallised from EtOAc/i-Pr2O, followed by CH2Cl2 /petroleum ether, to give 14f (180 mg, 48%), mp 224-234 (C (dec.). 1H NMR [(CD3)2SO] δ 11.54 (d, J=1.6 Hz, 1 H, NH), 9.17 (s, 1 H, H-4), 8.34 (dd, J=7.5, 2.2 Hz, 1 H, H-6), 8.22 (dd, J=7.1, 1.8 Hz, 1 H, H-9), 7.79-7.69 (m, 2 H, H-7,8), 7.17 (d, J=1.6 Hz, 1 H, H-3'), 7.16 (s, 1 H, H-4' or 7'), 6.99 (s, 1 H, H-4' or 7'), 4.91 (t, J=10.2 Hz, 1 H, H-2), 4.68 (dd, J=10.9, 2.4 Hz, 1 H, H-2), 4.65-4.57 (m, 1 H, H-1), 4.17-4.09 (m, 2 H, CH2Cl), 4.06 (t, J=6.0 Hz, 2 H, OCH2), 3.79 (s, 3 H, OCH3), 2.69 (t, J=5.9 Hz, 2 H, OCH2CH2), 2.26 (s, 6 H, N(CH3)2).

1. customgave a solid
2. customthe resulting gelatinous solid was collected
3. customchromatographed on alumina-90
4. washElution with EtOAc/MeOH (10:1)
5. customprovided the crude product which
6. customwas recrystallised from EtOAc/i-Pr2O