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

HRID 1531147ノート

反応式

HRID 1531147 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:19]([N:28]=2)=[C:20]2[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.Cl>N1CCCCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:21]1\[C:22](=[O:27])[NH:23][C:24]2[CH:25]=[CH:26][C:18]3[O:17][C:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[N:28][C:19]=3[C:20]\1=2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 112864661H-Pyrrole-2-carboxaldehyde, 3-methoxy-HCID 212534362-Phenyl-6,8-dihydro-oxazolo[4,5-e]indol-7-one

生成物 1

HCID 9841676(Z)-6,8-dihydro-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-phenyl-7H-pyrrolo[3,2-e]benzoxazol-7-one

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

3-Methoxypyrrole-2-carboxaldehyde (15 mg, 0.12 mmol) (prepared according to F. Bellamy et. al., J. Chem. Research (S) (1979), 18-19; J. Chem Research (M) (1979) 0101-0116), piperidine (3 drops)(Aldrich), and 2-phenyl-6,8-dihydro-oxazolo[4,5-e]indol-7-one (25 mg, 0.10 mmol)(from Example 2) were dissolved in DMF (1 mL). The mixture was heated to 90° C. and stirred at that temperature for 1 h. The mixture was cooled, poured into water, and acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate, and the combined organic extracts were washed with water, brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the crude product was purified by reverse phase HPLC with acetonitrile—water mixture as solvent. (Yield 3.6 mg, 8.4%)

後処理

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe crude product was purified by reverse phase HPLC with acetonitrile—water mixture as solvent

出典と根拠

ORDレコード
ord-80208a176909442db3a01851edab5e29
出典データセット
uspto-grants-2001_03
特許番号
US06197804B1

反応ノート

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