Cesium carbonate → HCID 24757938, compound

HRID 1925269Notes

Reaction equation

HRID 1925269 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:29]1[C:38]2[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=2)[N:32]=[CH:31][CH:30]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:29]4[C:38]5[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=5)[N:32]=[CH:31][CH:30]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 69200733HCID 69200733, compound

Product 1

HCID 24757938HCID 24757938, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The 6-hydroxy-naphthalene-1-carboxylic acid (4-chlorophenyl)-amide (Step a, 0.076 g, 0.254 mmol), Cs2CO3 (0.248 g, 0.762 mmol), 4-chloro-6,7-dimethoxy-quinoline (0.114 g, 0.508 mmol) and DMF (0.250 mL) were combined in a screw-cap test tube under N2. The tube was sealed and heated to 100° C. After 60 h at 100° C., the reaction was cooled to RT. The solvent was removed in vacuo, dissolved in EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered and concentrated. The residue remaining after concentration was dissolved in MeOH and purified by reverse-phase HPLC (pH 10 buffer solvent system). The fractions containing the desired product were concentrated, dissolved in EtOAc, and washed with brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound as a tan solid. M+H −485.1. Calc'd for C28H31N2O4−484.12.

Workup

  1. customThe tube was sealed
  2. temperaturethe reaction was cooled to RT
  3. customThe solvent was removed in vacuo
  4. dissolutiondissolved in EtOAc
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. concentrationafter concentration
  10. dissolutionwas dissolved in MeOH
  11. custompurified by reverse-phase HPLC (pH 10 buffer solvent system)
  12. additionThe fractions containing the desired product
  13. concentrationwere concentrated
  14. dissolutiondissolved in EtOAc
  15. washwashed with brine
  16. dry with materialThe organic layer was dried (Na2SO4)
  17. filtrationfiltered
  18. concentrationconcentrated

Sources & evidence

ORD record
ord-ed83978b528d4593b9608ec0804ee4c3
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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