Sodium Cyanide → HCID 58424882, compound

8-(hydroxymethyl)-6-(methoxymethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5-(6H)-one (100 mg, 0.36 mmol) prepared in step 5 of Example 41 was dissolved in dichloromethane (10 ml), added dropwise with thionylchloride (66 μl, 0.91 mmol) at 0° C. The resulting mixture was stirred at room temperature for 4 hours and poured into saturated sodium bicarbonate aqueous solution. The mixture was extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was then dissolved in N,N-dimethylformamide (5 ml) and sodium cyanide (55 mg, 1.09 mmol) was added. The resulting mixture was stirred at room temperature overnight and poured into ice water. The mixture was extracted with chloroform and the organic layer was washed with brine. The solution was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was then purified by flash column chromatography (chloroform:methanol=30:1) to obtain the title compound (70 mg, yield: 69%, white solid).

1. extractionThe mixture was extracted with dichloromethane
2. washwashed with brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated to dryness
5. dissolutionThe residue was then dissolved in N,N-dimethylformamide (5 ml)
6. stirringThe resulting mixture was stirred at room temperature overnight
7. extractionThe mixture was extracted with chloroform
8. washthe organic layer was washed with brine
9. dry with materialThe solution was dried over anhydrous sodium sulfate
10. customthe solvent was removed under reduced pressure
11. customThe residue was then purified by flash column chromatography (chloroform:methanol=30:1)

ORD record

ord-c97f74d4438447f59e73275c2ade8778

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815891B2