Water → N-[5-(3-hydroxyphenyl)-2-pyrazinyl]-3-oxospiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamide

HRID 2268066ノート

反応式

HRID 2268066 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[O:8]2)[CH2:4][CH2:3]1.[OH:17][C:18]1[CH:19]=[C:20]([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:21]=[CH:22][CH:23]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[OH:17][C:18]1[CH:19]=[C:20]([C:24]2[N:25]=[CH:26][C:27]([NH:30][C:31]([N:2]3[CH2:7][CH2:6][C:5]4([C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[C:9](=[O:16])[O:8]4)[CH2:4][CH2:3]3)=[O:32])=[N:28][CH:29]=2)[CH:21]=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 223806313H-spiro[isobenzofuran-1,4'-piperidin]-3-one hydrochlorideHCID 22660683Phenyl N-[5-(3-hydroxyphenyl)-2-pyrazinyl]carbamate

生成物 1

HCID 22660746N-[5-(3-hydroxyphenyl)-2-pyrazinyl]-3-oxospiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamide収率 34.7%

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 spiro[isobenzofuran-1(3H),4′-piperidine]-3-one hydrochloride (40 mg), phenyl N-[5-(3-hydroxyphenyl)-2-pyrazinyl]carbamate (51 mg) and triethylamine (119 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) and then dried over anhydrous Na2SO4. The concentration of the solvent left a residue, which was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2) followed by recrystallization from ethyl ether-hexane to give the subject compound (24 mg) as colorless crystals (melting point 257-259° 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. waitThe concentration of the solvent left a residue, which
  5. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2)
  6. customfollowed by recrystallization from ethyl ether-hexane

出典と根拠

ORDレコード
ord-2ef915f9cc6a4623816a0c6346b9199e
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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