Hydrochloric Acid → HCID 178462940, compound

HRID 1582984Notes

Reaction equation

[Cl: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[CH2:22][CH2:23][C:24]#[N:25])[CH:5]=[CH:6][CH:7]=1.[N-:26]=[N+:27]=[N-:28].[Na+].Cl.C(N(CC)CC)C.Cl>CN1CCCC1=O>[Cl: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[CH2:22][CH2:23][C:24]2[NH:28][N:27]=[N:26][N:25]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 700 mg of 4-(3-chlorophenyl)-3-(2-cyanoethyl)-1-ethyl-7-methyl-1,8-naphthyridin-2-(1H)-one, 388 mg of sodium azide, 411 mg of triethylamine hydrochloride and 10 ml of 1-methylpyrrolidin-2-one were stirred at 130° C. for 20 hours. The reaction mixture was cooled to room temperature, acidified by adding 1M hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine and the solvent was evaporated. The residue was purified by a silica gel column chromatography (hexane-ethyl acetate) and then recrystallized from ethyl acetate-diisopropyl ether to obtain 130 mg of 4-(3-chlorophenyl)-1-ethyl-7-methyl-3-[2-(1H-tetrazol-5-yl)ethyl]-1,8-naphthyridin-2(1H)-one as pale yellow crystals.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
customthe solvent was evaporated
customThe residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-d651a35ed13241dc83702319ab2f9916
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740662B1

Reaction notes

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