1,3-Dibromopropane → HCID 22667205, compound

HRID 1008470Notes

Reaction equation

HRID 1008470 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][CH2:23][CH2:24][CH3:25])=[O:21])=[C:15]([O:26][CH3:27])[CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][CH2:39]Br.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>CN(C)C=O.O>[CH3:27][O:26][C:15]1[CH:14]=[C:13]([O:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([O:1][CH2:37][CH2:38][CH2:39][N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)=[C:3]([O:28][CH3:29])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)[CH:18]=[CH:17][C:16]=1[NH:19][C:20]([NH:22][CH2:23][CH2:24][CH3:25])=[O:21]

Participants

7

Reactant 4

HCID 80011,3-DibromopropaneHCID 8083MorpholineHCID 11430Potassium Carbonate2×HCID 135674224HCID 135674224, compound

Product 1

HCID 22667205HCID 22667205, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

A starting compound (N-{4-[(7-hydroxy-6-methoxy-4-quinolyl)oxy]-2-methoxyphenyl}-N′-propylurea, 80 mg), potassium carbonate (138 mg), and 1,3-dibromopropane(0.10 ml) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was washed with ether to give an intermediate. The intermediate, potassium carbonate (138 mg), and morpholine (0.040 ml) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol to give 74 mg (yield 71%) of the title compound.

Workup

  1. extractionthe mixture was extracted with chloroform-propanol (3/1)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under the reduced pressure
  4. washThe residue was washed with ether
  5. customto give an intermediate
  6. stirringthe solution was stirred at room temperature for 18 hr
  7. extractionthe mixture was extracted with chloroform-propanol (3/1)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customthe solvent was removed by distillation under the reduced pressure
  10. customThe residue was purified by chromatography on silica gel by development with chloroform/methanol

Sources & evidence

ORD record
ord-f6ab257984644bc083824f4fe588ba20
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

Loading…