N-Methylaniline → HCID 178485594, compound

To a suspension of 7-chloro-3-(carboxy)pyrazolo[3,4-c][1]-benzazepine-4,10(1H,9H)-dione (500 mg, 1.72 mmol) (compound of Example 9) in carbon tetrachloride (5 mL) was added phosphorus pentachloride (358 mg, 1.72 mmol). The mixture was stirred for 17 hours, filtered and washed with carbon tetrachloride (3×10 mL). To the residue was added N-methylaniline (190 μL, 1.72 mmol) and dioxane (7 mL). The resulting mixture was stirred 17 hours. To this mixture was added water (50 mL). The aqueous layer was separated and extracted with ethyl acetate (3×100 mL). The organic layers were combined and concentrated by rotary evaporation to 50 mL. The insoluble material was removed by filtration and the organic solution was preabsorbed onto silica gel and purified by flash chromatography eluting with chloroform and chloroform:2-propanol (99:1, 98:2-90:10). The product fractions were combined and concentrated by rotary evaporation to give the title compound as a light yellow solid (100 mg, 15.2%, m.p. 308° C.).

1. filtrationfiltered
2. washwashed with carbon tetrachloride (3×10 mL)
3. stirringThe resulting mixture was stirred 17 hours
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (3×100 mL)
6. concentrationconcentrated by rotary evaporation to 50 mL
7. customThe insoluble material was removed by filtration
8. customthe organic solution was preabsorbed onto silica gel
9. custompurified by flash chromatography
10. washeluting with chloroform and chloroform:2-propanol (99:1, 98:2-90:10)
11. concentrationconcentrated by rotary evaporation

ORD record

ord-52f75d4ddd7643e1959692775ef0e8bc

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313290B1