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

HRID 2268057노트

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HRID 2268057 반응식
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[O:7][C:6]2=[O:17].[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:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][N:11]([C:31]([NH:30][C:27]3[CH:26]=[N:25][C:24]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:29][N:28]=3)=[O:32])[CH2:10][CH2:9]1)[O:7][C:6]2=[O:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 9879110Phenyl 5-phenylpyrazin-2-ylcarbamateHCID 226607305-Fluoro-3H-spiro[isobenzofuran-1,4'-piperidin]-3-one hydrochloride

생성물 1

HCID 99538015-fluoro-3-oxo-N-(5-phenyl-2-pyrazinyl)spiro[isobenzo-furan-1(3H),4'-piperidine]-1'-carboxamide수율 96.2%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
80 °C

실험 절차

A mixture of 5-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 (100 mg) as colorless crystals (melting point 236-238° C.).

후처리

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

출처 및 근거

ORD 기록
ord-837ffb29d59740f093269240a02cc15f
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326375B1

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