Potassium Carbonate → HCID 22490032、化合物

HRID 2180134

反応式

HRID 2180134 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[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[OH:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[CH:27]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH:29]1[C:30]2[C:26](=[CH:25][C:24]([O:23][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:22][CH2:21][CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[N:4][CH:3]=3)=[CH:32][CH:31]=2)[CH:27]=[CH:28]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 160545-HydroxyindoleHCID 112786904-Chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline

生成物 1

HCID 22490032HCID 22490032、化合物収率 15.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A suspension of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline (200 mg, 0.62 mmol), (prepared as described for the starting material in Example 1), 5-hydroxyindole (100 mg, 0.75 mmol) and potassium carbonate (129 mg, 0.93 mmol) in DMF (3 ml) was stirred at 100° C. for 6 hours. After cooling, the volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methylene chloride/methanol saturated with ammonia (98/2 to 90/10). The fractions containing the expected product were combined and evaporated to give 4-(indol-5-yloxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline (40 mg, 15%).

後処理

  1. custom(prepared
  2. temperatureAfter cooling
  3. customthe volatiles were removed under vacuum
  4. customthe residue was purified by column chromatography
  5. washeluting with methylene chloride/methanol saturated with ammonia (98/2 to 90/10)
  6. additionThe fractions containing the expected product
  7. customevaporated

出典と根拠

ORDレコード
ord-6f44e276deca477a96a2f8e2d995d84b
出典データセット
uspto-grants-2005_05
特許番号
US06887874B2

関連ノート

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