Piperidine → acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester

HRID 905836ノート

反応式

HRID 905836 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[CH2:5]2.N1CCCCC1.Cl[C:20]([C@@H:22]([O:24][C:25](=[O:27])[CH3:26])[CH3:23])=[O:21]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:20]([CH:22]([O:24][C:25](=[O:27])[CH3:26])[CH3:23])=[O:21])[NH:7][C:6](=[O:12])[CH2:5]2

参加物

5

反応物 3

HCID 8082PiperidineHCID 101035046-Amino-5-fluoroindolin-2-oneHCID 11094804(1S)-2-Chloro-1-methyl-2-oxoethyl acetate

生成物 1

HCID 59250052acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

The stirred solution of 5-fluoro-6-amino-1,3-dihydro-indol-2-one (450 mg, 2.71 mmol) in 10 ml of tetrahydrofuran was added with piperidine (0.4 ml). The mixture was cooled to −40° C. in an acetone-dry ice bath and added with (S)-acetic acid 1-chlorocarbonyl-ethyl ester (423 mg, 2.71 mmol) in 10 ml of tetrahydrofuran dropwise. Upon the completion of the addition, the resulting mixture was stirred at the room temperature overnight until the precipitate was formed. The solid was filtered, washed with water and recrystallized from methanol to give acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester (750 mg, 99%) as a white solid.

後処理

  1. additionUpon the completion of the addition
  2. customwas formed
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-63ea6040bbcf4f26ad43958b5d78c259
出典データセット
uspto-grants-2011_09
特許番号
US08012966B2

反応ノート

読み込み中…