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

HRID 2268057ノート

反応式

HRID 2268057 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-837ffb29d59740f093269240a02cc15f
出典データセット
uspto-grants-2001_12
特許番号
US06326375B1

反応ノート

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