Ethyl Acetate → HCID 90410171, compound

To a 0° C. mixture of 7-bromo-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (0.065 g, 0.20 mmol) from Example 1, step 4 and 4-(2-chloroethyl)morpholine hydrochloride (0.12 g, 0.63 mmol) in DMF (1 mL) was added NaH in mineral oil (0.048 g, 1.2 mmol). The reaction mixture was stirred over a weekend. EtOAc and water were added. The organic layer was washed with water and brine, dried over Na2SO4 and evaporated to dryness to give an orange oil. The crude was purified by LCMS (C18 column eluting with a gradient MeCN/H2O containing 0.15% NH4OH at 5 mL/min.) and gave a white solid (7.7 mg, 9% yield). 1H NMR (400 MHz, CD3OD/CDCl3): d 7.31 (3H, m); 7.18 (3H, m); 6.65 (1H, d); 5.19 (1H, m); 4.61 (1H, m); 4.43 (1H, m); 3.99 (2H, m); 3.6 (4H, m); 2.65 (2H, m); 2.51 (4H, m). LCMS calc. for C26H29N4O4 (M+H)+: m/z=. found: 444.1, 446.1.

1. washThe organic layer was washed with water and brine
2. dry with materialdried over Na2SO4
3. customevaporated to dryness
4. customto give an orange oil
5. customThe crude was purified by LCMS (C18 column
6. washeluting with a gradient MeCN/H2O containing 0.15% NH4OH at 5 mL/min.) and

ORD record

ord-df27fa9b4a7a4826b01955676d9c2135

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227985B2