HCID 12991185, compound → HCID 12991186, compound

HRID 1582997Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH:22]2[CH2:27][CH2:26][N:25](C(OCC)=O)[CH2:24][CH2:23]2)[CH:5]=[CH:6][CH:7]=1>Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 1.28 g of 4-(3-bromophenyl)-3-(1-ethoxycarbonylpiperidin-4-yl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one was added 20 ml of concentrated hydrochloric acid, followed by stirring at 100° C. for 3 hours. The solvent was evaporated and, after the residue was made alkaline by adding concentrated aqueous ammonia, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. After removal of the solvent from the organic layer, the resulting crude crystals were recrystallized from acetonitrile and then recrystallized from ethanol-water to obtain 357 mg of 4-(3-bromophenyl)-1-ethyl-7-methyl-3-(piperidin-4-yl)-1,8-naphthyridin-2(1H)-one as colorless crystals.

Workup

customThe solvent was evaporated
additionby adding concentrated aqueous ammonia
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customAfter removal of the solvent from the organic layer
customthe resulting crude crystals were recrystallized from acetonitrile
customrecrystallized from ethanol-water

Sources & evidence

ORD record: ord-c376080a92d14865b5836dec59fb5a23
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740662B1

Reaction notes

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