Hydrochloric Acid → (Z)-6,8-dihydro-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-phenyl-7H-pyrrolo[2,3-g]benzoxazol-7-one

HRID 1531149ノート

反応式

HRID 1531149 の反応式
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[CH:8]=O.[C:10]1([C:16]2[O:17][C:18]3[C:26]([N:27]=2)=[CH:25][CH:24]=[C:23]2[C:19]=3[CH2:20][C:21](=[O:28])[NH:22]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1CCCCC1.Cl>CC(O)C.O>[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:20]1\[C:21](=[O:28])[NH:22][C:23]2[CH:24]=[CH:25][C:26]3[N:27]=[C:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[O:17][C:18]=3[C:19]\1=2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 112864661H-Pyrrole-2-carboxaldehyde, 3-methoxy-HCID 212534292-Phenyl-6,8-dihydro-oxazolo[5,4-e]indol-7-one2 回

生成物 1

HCID 9928673(Z)-6,8-dihydro-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-phenyl-7H-pyrrolo[2,3-g]benzoxazol-7-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

3-Methoxypyrrole-2-carboxaldehyde (13 mg, 0.105 mmol)(Bellamy, supra) and 2-phenyl-6,8-dihydro-oxazolo[5,4-e]-indol-7-one (17 mg, 0.068 mmol)(Starting Material 4) were suspended in a solution of 10% piperidine (Aldrich) in 2-propanol (1 mL). The mixture was heated at reflux for 2 h. The mixture was cooled, poured into water, and the aqueous mixture was made acidic with concentrated hydrochloric acid. The aqueous layer was extracted with ethyl acetate, and the combined organic extracts were washed with water, brine, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and the crude product was purified by reverse phase HPLC using acetonitrile—water as solvent. (Yield 10 mg, 41%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic extracts were washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe crude product was purified by reverse phase

出典と根拠

ORDレコード
ord-ff83978482674ddabe83091d7a8edcc1
出典データセット
uspto-grants-2001_03
特許番号
US06197804B1

反応ノート

読み込み中…