Dimethylformamide → HCID 57567481, compound

HRID 1727871Notes

Reaction equation

HRID 1727871 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][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][N:16]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1.CN(C)C=O>O>[C:1]([C:5]1[CH:31]=[CH:30][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][CH2:40][CH2:41][N:42]5[CH2:47][CH2:46][O:45][CH2:44][CH2:43]5)=[C:22]([O:25][CH3:26])[CH:23]=4)[N:18]=[CH:17][N:16]=3)=[CH:12][CH:11]=2)=[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 136153640HCID 136153640, compound2×

Product 1

HCID 57567481HCID 57567481, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-{4-[4-(Tert-butyl)anilino]phenoxy}-6-methoxy-7-quinazolinol (starting compound 11) (100 mg), potassium carbonate (50 mg), and 4-(2-chloroethyl)morpholine hydrochloride (67 mg) were added to N,N-dimethylformamide (2 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 thin-layer chromatography on silica gel using chloroform/methanol for development to give the title compound (120 mg, yield 94%).

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 thin-layer chromatography on silica gel

Sources & evidence

ORD record
ord-983386c689024921b5cc91aa73519d2c
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

Loading…