Pyridine → HCID 59813881, compound

HRID 1925319Notes

Reaction equation

HRID 1925319 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:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([NH2:26])=[CH:23]2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1.[C:39]1([CH3:49])[CH:44]=[CH:43][CH:42]=[C:41]([S:45](Cl)(=[O:47])=[O:46])[CH:40]=1>C(Cl)Cl.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:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([NH:26][S:45]([C:41]3[CH:42]=[CH:43][CH:44]=[C:39]([CH3:49])[CH:40]=3)(=[O:47])=[O:46])=[CH:23]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 27345953-Methylbenzenesulphonyl chlorideHCID 67520515HCID 67520515, compound

Product 1

HCID 59813881HCID 59813881, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-(6,7-dimethoxyquinolin-4-yloxy)naphthalen-2-amine (0.168 g, 0.48 mmol) in 20 mL of CH2Cl2 was added K2CO3 (0.134 g, 0.96 mmol), and pyridine (1 mL). The mixture was cooled to 0° C. and m-toluenesulfonyl chloride (0.110 g, 0.58 mmol) was added and the solution was stirred for 16 h at RT under an atmosphere of nitrogen. The reaction was diluted with water and extracted with CH2Cl2 3×. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a Gilson Prep HPLC system. The fractions were collected, combined, treated with NaHCO3(aq) and extracted with EtOAc 3×. The organic layer was dried (Na2SO4), filtered and concentrated to afford the desired compound. MS (ESI, pos. ion) m/z: 501.0 (M+1). Mass Calc'd for C28H24N2O5S: 500.573.

Workup

  1. extractionextracted with CH2Cl2 3×
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customThe fractions were collected
  8. additiontreated with NaHCO3(aq)
  9. extractionextracted with EtOAc 3×
  10. dry with materialThe organic layer was dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-b759a703d3244cd79d3d1939ec458ca9
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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