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Dichloromethane → (E)-4-Methyl-1-[(3S)-3-(4-quinolylamino)pyrrolidin-1-yl]pent-2-en-1-one

HRID 333940
ノート
印刷プレビュー

反応式

HRID 333940 の反応式
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)[CH2:2]1.C(N(CC)CC)C.ClCCl.[CH3:27][CH:28]([CH3:34])/[CH:29]=[CH:30]/[C:31](Cl)=[O:32].ClCCl.C1(C)C(S(Cl)(=O)=O)=CC=CC=1>>[CH3:27][CH:28]([CH3:34])/[CH:29]=[CH:30]/[C:31]([N:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)[CH2:2]1)=[O:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6344DichloromethaneHCID 8623o-Toluenesulfonyl chlorideHCID 10986269(E)-4-methylpent-2-enoyl ChlorideHCID 21882572Triethylamine methylene chlorideHCID 66835796N-[(3S)-Pyrrolidin-3-yl]quinolin-4-amine

生成物 1

HCID 56948960(E)-4-Methyl-1-[(3S)-3-(4-quinolylamino)pyrrolidin-1-yl]pent-2-en-1-one
収率 39%

実験手順

To N-[(3S)-Pyrrolidin-3-yl]quinolin-4-amine (32 mg, 0.15 mmol) dissolved in 1.5 ml anhydrous dichloromethane triethylamine (0.9 mmol, 91 mg) was added with stirring followed by (E)-4-methylpent-2-enoyl chloride dissolved in anhydrous dichloromethane (29.8 mg, 0.23 mmol). The mixture was stirred at room temperature for 5 minutes after which polymer-supported toluenesulfonyl chloride (600 mg, 1-2 mmol/g) was added and the mixture was shaken for 15 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 18 mg of a solid (0.58 mmol, 39%).

後処理

  1. additionwas added
  2. additionwas added
  3. stirringthe mixture was shaken for 15 minutes
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness under reduced pressure
  6. 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-920f4f85a70e48439c2c4dcfabcd2c2c
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08883791B2

反応ノート

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