Potassium Carbonate → N-(6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-2-naphthalenyl)-2-(methoxy)benzamide

HRID 1925241Notes

Reaction equation

HRID 1925241 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.C([O-])([O-])=O.[K+].[K+].[CH3:33][O:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38]>C(Cl)Cl>[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:37](=[O:38])[C:36]1[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=1[O:34][CH3:33])[CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 889692-Methoxybenzoyl chlorideHCID 675205556-(6,7-Dimethoxy-4-quinolyloxy)-2-naphthylamine

Product 1

HCID 11397470N-(6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-2-naphthalenyl)-2-(methoxy)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-(6,7-dimethoxy-4-quinolyloxy)-2-naphthylamine (Step c, 34.6 mg, 0.1 mmol) and K2CO3 in dry CH2Cl2 (10 mL, Aldrich) was added 2-methoxybenzoyl chloride (25.5 mg, 0.15 mmol, Aldrich). The reaction was stirred at RT for 3 h. The volatile portion was removed in vacuo. To the residue was added 15 mL of MeOH and the mixture was stirred at RT for 30 min. The MeOH was removed in vacuo. The resulting residue was diluted in EtOAc (50 mL) and washed with water and brine. The organic phase was dried over MgSO4 and concentrated. The resulting brown residue was purified by silica gel column chromatography (EtOAc) to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 481.4 (M+1). Mass Calc'd for C29H24N2O5: 480.17.

Workup

  1. customThe volatile portion was removed in vacuo
  2. additionTo the residue was added 15 mL of MeOH
  3. stirringthe mixture was stirred at RT for 30 min
  4. customThe MeOH was removed in vacuo
  5. additionThe resulting residue was diluted in EtOAc (50 mL)
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated
  9. customThe resulting brown residue was purified by silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-3ca144cbafcb4be385c546f99918d022
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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