Hydrogen Bromide → HCID 22004348, compound

HRID 324353Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10](Cl)=[N:9][N:8]=1.Br.[C:25](=[O:28])([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[C:10]([N:6]([CH2:5][CH2:4][CH2:25][OH:28])[CH3:7])=[N:9][N:8]=[C:7]2[NH:6][CH2:5][C:4]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:2]([Cl:1])[CH:3]=1

Participants

Conditions

Temperature: 170 °C

Procedure

The compound (1.0 g, 2.7 mmol) prepared in Example 27 was dissolved in 9 ml of N-methyl-2-pyrrolidone, followed by the addition of 0.7 g (4.1 mmol) of N-methylpropanolamine hydrobromide and 1.14 g (8.2 mmol) of anhydrous potassium carbonate. The obtained mixture was stirred at 170° C. for 7.5 hours, followed by the addition of water. The resulting mixture was extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and freed from the solvent by distillation. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (20:1)] and crystallized from dichloromethane/ether to give 37 mg of the title compound as white needles.

Workup

extractionThe resulting mixture was extracted with ethyl acetate
washThe organic phase was washed with water
dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
distillationfreed from the solvent by distillation
customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (20:1)]
customcrystallized from dichloromethane/ether

Sources & evidence

ORD record: ord-9225631f151c422fbf26d1f2fd649dba
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218392B1

Reaction notes

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