Dimethylformamide → HCID 57567488, compound

HRID 1727872Notes

Reaction equation

HRID 1727872 reaction equation
[C:1]([C:5]1[CH:32]=[CH:31][C:8]([NH:9][C:10]2[CH:29]=[CH:28][C:13]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([OH:27])=[C:22]([O:25][CH3:26])[CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[CH:12][C:11]=2[F:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1.CN(C)C=O>O>[C:1]([C:5]1[CH:32]=[CH:31][C:8]([NH:9][C:10]2[CH:29]=[CH:28][C:13]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:27][CH2:41][CH2:42][N:43]5[CH2:48][CH2:47][O:46][CH2:45][CH2:44]5)=[C:22]([O:25][CH3:26])[CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[CH:12][C:11]=2[F:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 136153638HCID 136153638, compound2×

Product 1

HCID 57567488HCID 57567488, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-{4-[4-(Tert-butyl)anilino]-3-fluorophenoxy}-6-methoxy-7-quinolinol (starting compound 6) (1.75 g), potassium carbonate (2.80 g), and 4-(2-chloroethyl)morpholine hydrochloride (1.13 g) were added to N,N-dimethylformamide (20 ml), and the mixture was stirred at 80° C. overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and was dried over sodium sulfate. The solvent was then removed by evaporation under the reduced pressure. The crude thus obtained was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (1.44 g, yield 64%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was then removed by evaporation under the reduced pressure
  5. customThe crude thus obtained
  6. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-245a029162894305850699d483f1af5a
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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