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Gamma-Butyrolactone → HCID 58382148、化合物

HRID 1628010
ノート
印刷プレビュー

反応式

HRID 1628010 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[N:20]=[C:15]2[CH:14]=1.[O:32]1[CH2:36][CH2:35][CH2:34][C:33]1=[O:37].N1C=NC=N1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[OH:37][CH2:33][CH2:34][CH2:35][C:36]([NH:22][CH2:21][C:19]1[N:20]=[C:15]2[CH:14]=[C:13]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH3:12])[CH:7]=3)[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:16]2=[N:17][CH:18]=1)=[O:32]
参加物反応条件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 7302Gamma-ButyrolactoneHCID 92571H-1,2,4-TriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58009787HCID 58009787、化合物

生成物 1

HCID 58382148HCID 58382148、化合物収率 42%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
60 °C

実験手順

A flask was charged with (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.300 g, 0.686 mmol, Preparation #I.1), dihydrofuran-2(3H)-one (0.063 mL, 0.823 mmol), 1,2,4-triazole (0.009 g, 0.13 mmol), DBU (0.021 mL, 0.13 mmol) and DCM (10 mL). The mixture was heated to about 60° C. and stirred overnight. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (10 mL) and washed with water (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The material was purified by silica gel chromatography with an elution gradient of 0 to 100% EtOAc/heptane to give 4-hydroxy-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanamide (0.150 g, 42%): LC/MS (Table 2, Method b) Rt=2.40 min; MS m/z 524 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with EtOAc (10 mL)
  3. washwashed with water (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe material was purified by silica gel chromatography with an elution gradient of 0 to 100% EtOAc/heptane

出典と根拠

ORDレコード
ord-184758e4f61641e0a84465ccdf305530
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785639B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート