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

HRID 1249822Notes

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-a11c235f7ba14ca7a6eaa7da8d87d85c
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06335345B1

Reaction notes

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