Potassium Carbonate → 6-Methoxy-(4-nitroindol-5-yloxy)-7-(3-piperidinopropoxy)quinazoline

HRID 454308ノート

反応式

HRID 454308 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:30][C:31]1[C:32]([N+:40]([O-:42])=[O:41])=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][CH:35]=[CH:34]2>CC(N(C)C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[N:5]=[C:4]([O:30][C:31]1[C:32]([N+:40]([O-:42])=[O:41])=[C:33]3[C:37](=[CH:38][CH:39]=1)[NH:36][CH:35]=[CH:34]3)[N:3]=[CH:2]2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazolineHCID 156921694-nitro-1H-indol-5-ol

生成物 1

HCID 220307416-Methoxy-(4-nitroindol-5-yloxy)-7-(3-piperidinopropoxy)quinazoline収率 39%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
90 °C

実験手順

Nitrogen was bubbled through a mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (114 mg, 0.34 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (141 mg, 1.02 mmol), 5-hydroxy-4-nitroindole (60.5 mg, 0.34 mmol) and DMA (8.5 ml) for 5 minutes at ambient temperature. This mixture was then stirred at 90° C. for 4 hours under an atmosphere of nitrogen and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated in vacuo. The residue was purified by silica column chromatography using gradient elution with dichloromethane/methanol (100/0 to 95/5) followed by dichloromethane/methanolic ammonia (7M) (95/5) to give a partially purified oil. This oil was further purified by silica column chromatography, gradient elution with ethyl acetate/methanolic ammonia (95/5 to 80/20) to give 6-methoxy-(4-nitroindol-5-yloxy)-7-(3-piperidinopropoxy)quinazoline (63 mg, 39%).

後処理

  1. custom(prepared
  2. customfor 5 minutes
  3. customat ambient temperature
  4. temperatureto cool to ambient temperature
  5. filtrationThe reaction mixture was filtered
  6. customthe filtrate evaporated in vacuo
  7. customThe residue was purified by silica column chromatography
  8. washelution with dichloromethane/methanol (100/0 to 95/5)
  9. customto give a partially purified oil
  10. customThis oil was further purified by silica column chromatography, gradient elution with ethyl acetate/methanolic ammonia (95/5 to 80/20)

出典と根拠

ORDレコード
ord-2909bf485a8d469ea2de8b78ea70896e
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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