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Potassium Iodide → 6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]-7-{[1-(pyrrolidin-1-ylacetyl)piperidin-4-yl]methoxy}quinazoline

HRID 1668675
ノート
印刷プレビュー

反応式

HRID 1668675 の反応式
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([O:23][C:24]4[CH:25]=[C:26]5[C:30](=[CH:31][CH:32]=4)[NH:29][CH:28]=[C:27]5[CH3:33])=[N:18][CH:19]=[N:20]3)=[CH:15][C:14]=2[O:34][CH3:35])[CH2:7][CH2:6]1)=[O:4].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.[I-].[K+]>CN(C=O)C>[CH3:35][O:34][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:13]=1[O:12][CH2:11][CH:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:6][CH2:7]1)[N:20]=[CH:19][N:18]=[C:17]2[O:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[CH3:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 4875Potassium IodideHCID 31268PyrrolidineHCID 596829177-{[1-(chloroacetyl)piperidin-4-yl]methoxy}-6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]quinazoline

生成物 1

HCID 596829086-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]-7-{[1-(pyrrolidin-1-ylacetyl)piperidin-4-yl]methoxy}quinazoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 7-{[1-(chloroacetyl)piperidin-4-yl]methoxy}-6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]quinazoline (0.118 g), pyrrolidine (0.059 ml), potassium iodide (0.01 g) and DMF (3 ml) was stirred and heated to 80° C. for 40 minutes. The mixture was cooled to ambient temperature, the solvent was removed by evaporation under vacuum and the residue was purified by column chromatography on silica using increasingly polar solvent mixtures, starting with dichloromethane and ending dichloromethane/methanol saturated with ammonia (3.5M) (94/6). Evaporation of the solvents gave a foam which was triturated under ether/pentane (70/30) to give a solid which was collected by filtration and dried under vacuum to give 6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]-7-{[1-(pyrrolidin-1-ylacetyl)piperidin-4-yl]methoxy}quinazoline (0.096 g).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solvent was removed by evaporation under vacuum
  3. customthe residue was purified by column chromatography on silica using
  4. temperatureincreasingly polar solvent mixtures
  5. customEvaporation of the solvents
  6. customgave a foam which
  7. customwas triturated under ether/pentane (70/30)
  8. customto give a solid which
  9. filtrationwas collected by filtration
  10. customdried under vacuum

出典と根拠

ORDレコード
ord-2100e3c2c3854df9aabd9a30749158f1
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989460B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート