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Gamma-Butyrolactone → HCID 58382148, 화합물

HRID 1628010
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HRID 1628010 반응식
[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]
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참가 물질

6

반응물 4

HCID 7302Gamma-ButyrolactoneHCID 92571H-1,2,4-TriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58009787HCID 58009787, 화합물

생성물 1

HCID 58382148HCID 58382148, 화합물수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

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온도
60 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-184758e4f61641e0a84465ccdf305530
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785639B2

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