Chloroform → N-[6-(6,7-dimethoxy-quinolin-4-yloxy)-naphthalen-1-yl]-2-fluoro-benzamide

HRID 2115781Notes

Reaction equation

HRID 2115781 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)[C:22]([NH2:26])=[CH:21][CH:20]=[CH:19]2.C([O-])(O)=O.[Na+].[F:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36].C(Cl)(Cl)Cl>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:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([NH:26][C:35](=[O:36])[C:34]1[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=1[F:32])=[CH:21][CH:20]=[CH:19]2

Participants

7

Reactant 4

HCID 6212ChloroformHCID 98082-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 675202746-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Product 1

HCID 59813576N-[6-(6,7-dimethoxy-quinolin-4-yloxy)-naphthalen-1-yl]-2-fluoro-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(6,7-dimethoxy-quinolin-4-yloxy)-naphthalen-1-ylamine (Step a, 50 mg, 0.14 mmol) and NaHCO3 (38 mg, 0.45 mmol) in CH2Cl2 (1 mL), 2-fluorobenzoyl chloride (18 mL, 0.15 mmol) was added. The reaction was stirred at RT for 20 h. The mixture was taken up into CHCl3 and water, washed with brine, dried with Na2SO4, filtered and concentrated in vacuo. The title compound was purified by column chromatography using 0-100% of a 90:10:1 (CH2Cl2:MeOH:NH4OH) solution as the eluant. M+H 469.1, Calc'd for C28H21FN2O4-468.49.

Workup

  1. washwashed with brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe title compound was purified by column chromatography

Sources & evidence

ORD record
ord-24eda6a5a5064348a5dd62306510b44b
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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