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Dicyclohexylcarbodiimide → (E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

HRID 333948
ノート
印刷プレビュー

反応式

HRID 333948 の反応式
[OH:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C1CCC(N=C=NC2CCCCC2)CC1.C1C=NC2N(O)N=NC=2C=1.[CH3:34][C:35]1[CH:44]=[C:43]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=1>CN(C=O)C>[OH:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([N:48]1[CH2:49][CH2:50][N:45]([C:43]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]=[C:35]([CH3:34])[CH:44]=2)[CH2:46][CH2:47]1)=[O:7]
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 4

HCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 7023182-Methyl-4-(piperazin-1-yl)quinolineHCID 53636584-Hydroxy-pent-2-enoic acid

生成物 1

HCID 86691596(E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

(E)-4-Hydroxypent-2-enoic acid (67 mg, 0.52 mmol) was dissolved in anhydrous DMF (2.5 ml), DCC (107.5, 0.52 mmol) and HOAt (106.7 mg, 0.79 mmol) were added and the mixture was stirred at room temperature for 15 minutes. 2-Methyl-4-piperazin-1-yl-quinoline (118.2 mg, 0.52 mmol) was added and stirring was continued for 90 minutes. The mixture was evaporated to dryness, taken up in a mixture of acetonitrile and methanol and filtered. The filtrate was evaporated to dryness again and purified by preparative HPLC (gradient of water containing 0.1% TFA and acetonitrile). 110 mg were obtained (0.33 mmol, 65%). MS (ES): m/z=326.1 [M+1]+.

後処理

  1. stirringstirring
  2. waitwas continued for 90 minutes
  3. customThe mixture was evaporated to dryness
  4. additiontaken up in a mixture of acetonitrile and methanol
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness again
  7. custompurified by preparative HPLC (gradient of water containing 0.1% TFA and acetonitrile)
  8. custom110 mg were obtained (0.33 mmol, 65%)

出典と根拠

ORDレコード
ord-f702141a66674518bc41b725648f1e79
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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