Sodium Carbonate → 1,1-dimethylethyl {4'-[1-[[(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetyl](methyl)amino]-2-(4-morpholinyl)ethyl]-3-biphenylyl}carbamate

To a solution of N-[1-(4-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide (3.28 g, 5.8 mmol) and [3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)phenyl]boronic acid (2.00 g, 8.4 mmol) in DMF (15 mL) was added Pd(dppf)Cl2 (0.24 g, 0.29 mmol) and 2N solution of Na2CO3 (11.6 mL, 23.2 mmol). The resultant mixture was stirred at 80° C. for 16 h. The mixture was filtered through a bed of celite and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and washed with 5% NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried over MgSO4 and concentrated. The residue was dissolved in methanol, and water was added to precipitate a tan solid. The solid was collected by filtration and air dried to give 1.55 g (40%) of the title compound a tan solid. MS (ES) m/e 669 [M+H]+

1. filtrationThe mixture was filtered through a bed of celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
4. washwashed with 5% NaHCO3 (100 mL) and brine (100 mL)
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in methanol
8. additionwater was added
9. customto precipitate a tan solid
10. filtrationThe solid was collected by filtration and air
11. customdried

ORDレコード

ord-bfa274f5740c4355aab983a9f50bd4ad

出典データセット

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07432258B2