Water → 6-fluoro-3-oxo-N-(5-phenyl-2-pyrazinyl)spiro-[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamide

HRID 392792Notes

Reaction equation

Cl.[F:2][C:3]1[CH:16]=[C:15]2[C:6]([C:7](=[O:17])[O:8][C:9]32[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[CH:5][CH:4]=1.[C:18]1([C:24]2[N:25]=[CH:26][C:27]([NH:30][C:31](=O)[O:32]C3C=CC=CC=3)=[N:28][CH:29]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[F:2][C:3]1[CH:16]=[C:15]2[C:6]([C:7](=[O:17])[O:8][C:9]32[CH2:14][CH2:13][N:12]([C:31]([NH:30][C:27]2[CH:26]=[N:25][C:24]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:29][N:28]=2)=[O:32])[CH2:11][CH2:10]3)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-fluorospiro[isobenzofuran-1(3H),4′-piperidine]-3-one hydrochloride (64 mg), phenyl N-(5-phenyl-2-pyrazinyl)carbamate (73 mg) and triethylamine (174 μL) in chloroform (5 mL) was stirred at 80° C. for 2 hours. The reaction mixture was poured into water and extracted with chloroform (20 mL). The organic layer was washed with saturated saline solution (20 mL), then dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2) and recrystallized from ethyl ether-hexane to give the subject compound (101 mg) as colorless crystals (melting point 222-224° C.).

Workup

extractionextracted with chloroform (20 mL)
washThe organic layer was washed with saturated saline solution (20 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2)
customrecrystallized from ethyl ether-hexane

Sources & evidence

ORD record: ord-9d4cfa75157943fd8fd74f13d46ed1dc
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803372B2

Reaction notes

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