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

HRID 333943노트

반응식

HRID 333943 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4dee199dcb1f46eeacecebe808339dd8
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883791B2

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