Diisopropylethylamine → n-[6-((6,7-Dimethoxy-4-quinolyl)oxy) (2-naphthyl)](2-fluoro-3-pyridyl)carboxamide

HRID 1925242Notes

Reaction equation

HRID 1925242 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH2:26])[CH:20]=[CH:19]2.[F:27][C:28]1[C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=[CH:30][N:29]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH:26][C:34]([C:33]1[C:28]([F:27])=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:35])[CH:20]=[CH:19]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 960892-Fluoronicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 675205556-(6,7-Dimethoxy-4-quinolyloxy)-2-naphthylamine

Product 1

HCID 59813676n-[6-((6,7-Dimethoxy-4-quinolyl)oxy) (2-naphthyl)](2-fluoro-3-pyridyl)carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(6,7-Dimethoxy-4-quinolyloxy)-2-naphthylamine (69.2 mg, 0.2 mmol, Example 1c), 2-fluoropyridine-3-carboxylic acid (33.8 mg, 0.24 mmol, Maybridge), DIEA (31 mg, 0.24 mmol, Aldrich) and TBTU (91.2 mg, 0.24 mmol, Advanced ChemTech) were stirred in 6 mL of dry DMF at RT for 24 h. The solution was diluted with 50 mL of EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc) to give title compound as a white solid. MS (ESI, pos. ion) m/z: 470.0 (M+1). Mass Calc'd for C27H20FN3O4: 469.14.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-c1115df3aa9d481d8594dfea65d9454e
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

Loading…