反应详情

温度

-78 °C

To a solution of 6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide (intermediate 57, 0.040 g, 0.0771 mmol) in THF (0.6 mL) at −78° C was added thiophosgene (0.010 mL). After stirring for 1 h at −78° C, the reaction was quenched with saturated aqueous NaHCO3 and the product was extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by SiO2 column chromatography, eluting with mixtures of EtOAc in hexanes, to provide the title compound. LC/MS: m/e 562.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.22 (1H, d, J=1.8 Hz), 7.82 (1H, dd, J=8.4, 2.0 Hz), 7.65 (1H, d, J=7.4 Hz), 7.17 (1H, d, J=7.5 Hz), 7.13-7.16 (2H, m), 7.10 (1H, br s), 6.97-6.99 (2H, m), 6.88 (1H, d, J=8.5 Hz), 4.70-4.95 (2H, br), 1.25 (9H, s).

1. customthe reaction was quenched with saturated aqueous NaHCO3
2. extractionthe product was extracted with EtOAc
3. washThe combined extracts were washed with brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe residue was purified by SiO2 column chromatography
7. washeluting with mixtures of EtOAc in hexanes