Cesium carbonate → 6-(3-Carbamoyl-6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid

HRID 1925314Notes

Reaction equation

HRID 1925314 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][C:23]=1[C:36]([NH2:38])=[O:37]>CN(C=O)C>[C:36]([C:23]1[CH:24]=[N:25][C:26]2[C:31]([C:22]=1[O:1][C:2]1[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]3)=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)(=[O:37])[NH2:38]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 54638006-Hydroxy-1-naphthoic acidHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 675202686-(3-Carbamoyl-6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A resealable tube was charged with 6-hydroxy-1-naphthoic acid (0.035 g, 0.187 mmol), cesium carbonate (0.183 g, 0.561 mmol), and DMF (1.0 mL). The system was flushed with argon, the tube was sealed, and the mixture stirred at RT for 15 min. 4-Chloro-6,7-dimethoxyquinoline-3-carboxamide (0.050 g, 0.187 mmol) mL) was added (along with a 1 mL DMF rinse), and the system was again flushed with argon. The tube was sealed and the mixture stirred at 60° C. for 26 h. The reaction mixture was diluted with water (2.5 mL) and 6 N HCl (aq) was added dropwise with stirring until the pH of the solution was 5-6. The resulting precipitate was filtered and washed with water. The filter cake was dried under vacuum to afford 6-(3-carbamoyl-6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid as a tan solid. MS (ESI, pos. ion) m/z: 419.0 (M+H). Mass Calc'd for C23H18N2O6: 418.

Workup

  1. customThe system was flushed with argon
  2. customthe tube was sealed
  3. washrinse), and the system
  4. customwas again flushed with argon
  5. customThe tube was sealed
  6. stirringthe mixture stirred at 60° C. for 26 h
  7. additionThe reaction mixture was diluted with water (2.5 mL) and 6 N HCl (aq)
  8. additionwas added dropwise
  9. stirringwith stirring until the pH of the solution
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with water
  12. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-0bc55f7b2e4d44198016d75f041468ef
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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