Morpholine → HCID 178520048, compound

Morpholine (268 μL, 3.06 mmol) was added to a solution of trimethylaluminum in toluene (1.56 mL, 3.13 mmol) and the solution was stirred for 20 minutes. A portion (365 μL) of the resulting solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (100 mg, 0.313 mmol) in toluene (0.760 mL). The resulting solution was stirred for 4 hours at room temperature and then quenched with aqueous hydrochloric acid (1.88 mL, 1N) and water (50 mL). The aqueous layer was extracted with chloroform (7×50 mL) and ethyl acetate (3×50 mL). The combined organic layers were concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20) to give the title compound (89.9 mg, 80% yield, m.p. 347° C.).

1. stirringThe resulting solution was stirred for 4 hours at room temperature
2. customquenched with aqueous hydrochloric acid (1.88 mL, 1N) and water (50 mL)
3. extractionThe aqueous layer was extracted with chloroform (7×50 mL) and ethyl acetate (3×50 mL)
4. concentrationThe combined organic layers were concentrated on a rotary evaporator
5. customThe crude product was purified by flash chromatography
6. washeluting with chloroform:2-propanol (99:1-80:20)

ORD record

ord-630c4e5544b246d5b5dc9109744d39a0

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313290B1