Sodium borohydride → HCID 54763442, compound

Participants

Reaction Steps

To a solution of {8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-5-[(6-chloropyridin-3-yl)methyl]-7-oxo-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-9-yl}acetaldehyde (see Example 22, 0.030 g, 0.053 mmol) in a mixture of 0.4 mL of dichloromethane and 0.1 mL of methanol at 0° C. was added sodium borohydride (2.0 mg, 0.053 mmol). The mixture was allowed to warm to ambient temperature and after 15 hr, hydrochloric acid (3 N aqueous, 5 drops) was added. After 24 hr, the mixture was diluted with saturated aqueous sodium bicarbonate and extracted 3× with ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the titled compound that gave a mass ion (ES+) of 452.1735 for [M+H]+ [calc'd for C25H27ClN3O3, [M+H]+=452.1735]: 1H NMR (400 MHz, CD3OD) δ 9.00-8.98 (m, 1H), 8.62-8.59 (m, 1H), 8.31-8.30 (m, 1H), 7.69 (s, 1H), 7.65-7.62 (m, 2H), 7.37 (d, J=8.3 Hz, 1H), 5.44-5.41 (m, 2H), 4.60 (s, 2H), 4.42-4.36 (m, 1H), 3.76-3.66 (m, 1H), 3.15-3.01 (m, 2H), 2.58-2.51 (m, 1H), 2.16-2.13 (m, 1H), 1.97-1.93 (m, 2H), 1.82-1.79 (m, 2H), 1.46-1.40 (m, 3H) ppm.

Provenance & Evidence