Trifluoroacetic acid → N-[1-(3'-amino-4-biphenylyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide

HRID 2354429Notes

Reaction equation

HRID 2354429 reaction equation
[Cl:1][C:2]1[C:3]([Cl:46])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][C:13]([N:15]([CH3:44])[CH:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([NH:36]C(=O)OC(C)(C)C)[CH:31]=4)=[CH:26][CH:25]=3)[CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:14])[C:6]=2[CH:45]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:36][C:32]1[CH:31]=[C:30]([C:27]2[CH:28]=[CH:29][C:24]([CH:16]([N:15]([CH3:44])[C:13](=[O:14])[CH2:12][N:7]3[C:6]4[CH:45]=[C:2]([Cl:1])[C:3]([Cl:46])=[CH:4][C:5]=4[O:10][CH2:9][C:8]3=[O:11])[CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:25][CH:26]=2)[CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574890281,1-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

Product 1

HCID 57489027N-[1-(3'-amino-4-biphenylyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamideYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 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 (1.55 g, 2.3 mmol) in dichloromethane (8 mL) was added trifluoro acetic acid (8 mL). The resultant mixture was stirred at room temperature for 2 h. The mixture was concentrated under reduced pressure. The residue was purified by using a Gilson preparative HPLC (Phenomenex, 100×50 mm, 10 micron, 90 mL/min, A: acetonitrile, 0.1% TFA B: water, 0.1% TFA, A: 10 to 90% over 15 min, UV detection at 214 nm) to give 0.66 g (50%) of the title compound as tan solid MS (ES) m/e 569.1 [M+H]+

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified

Sources & evidence

ORD record
ord-42900a5074844f98a84dadd014a757b4
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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