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

HRID 1925273Notes

Reaction equation

HRID 1925273 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-1f9fc363eab6403fabdda85b7af66eb4
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

Loading…