Diisopropylethylamine → (E)-1-[(1S,4S)-5-(4-Quinolyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]hex-2-en-1-one

HRID 333943ノート

反応式

HRID 333943 の反応式
Cl.[C@H:2]12[CH2:18][C@H:5]([N:6]([C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=[CH:10][CH:9]=3)[CH2:7]1)[CH2:4][NH:3]2.C(N(C(C)C)CC)(C)C.[C:28](Cl)(=[O:34])/[CH:29]=[CH:30]/[CH2:31][CH2:32][CH3:33]>ClCCl>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([N:6]2[CH2:7][C@@H:2]3[CH2:18][C@H:5]2[CH2:4][N:3]3[C:28](=[O:34])/[CH:29]=[CH:30]/[CH2:31][CH2:32][CH3:33])=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 5706484(E)-hex-2-enoyl chlorideHCID 668355714-[(1S,4S)-2,5-Diazabicyclo[2.2.1]heptan-5-yl]quinoline hydrochloride

生成物 1

HCID 66835855(E)-1-[(1S,4S)-5-(4-Quinolyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]hex-2-en-1-one収率 28%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To 4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-5-yl]quinoline hydrochloride (26.2 mg, 0.1 mmol), dissolved in 0.5 ml anhydrous dichloromethane, polymer-supported diisopropylethylamine (80 mg, 3-4 mmol/g) was added followed by (E)-hex-2-enoyl chloride (19.9 mg, 0.15 mmol) dissolved in anhydrous dichloromethane (1 ml). The mixture was shaken at room temperature for 20 minutes, filtered and the filtrate evaporated to dryness under reduced pressure. The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 9 mg of a solid (0.028 mmol, 28%).

後処理

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. customThe raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

出典と根拠

ORDレコード
ord-4dee199dcb1f46eeacecebe808339dd8
出典データセット
uspto-grants-2014_11
特許番号
US08883791B2

反応ノート

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