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Dimethylformamide → 5-[2-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl]-2-oxa-5-azabicyclo[2.2.1]heptane

HRID 928568
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HRID 928568 반응식
CS(O[CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH:13]2[CH2:15][CH:10]1[CH2:11][N:12]2[C:16]1[C:17]2[C:24]([CH:25]([CH3:27])[CH3:26])=[CH:23][S:22][C:18]=2[N:19]=[CH:20][N:21]=1)(=O)=O.Cl.[CH:29]12[CH2:35][CH:32]([NH:33][CH2:34]1)[CH2:31][O:30]2.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(C(C)=O)C.C(Cl)Cl>[CH:25]([C:24]1[C:17]2[C:16]([N:12]3[CH2:11][CH:10]4[CH2:15][CH:13]3[CH2:14][CH:9]4[O:8][CH2:7][CH2:6][N:33]3[CH2:34][CH:29]4[CH2:35][CH:32]3[CH2:31][O:30]4)=[N:21][CH:20]=[N:19][C:18]=2[S:22][CH:23]=1)([CH3:27])[CH3:26]
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 219143642-Oxa-5-azabicyclo[2.2.1]heptane hydrochlorideHCID 895794842-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl methanesulfonate

생성물 1

HCID 895796045-[2-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl]-2-oxa-5-azabicyclo[2.2.1]heptane
수율 17.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6569Methyl Ethyl Ketone용매

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온도
180 °C

실험 절차

2-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl methanesulfonate (0.11 g, 0.27 mmol), 2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride (0.072 g, 0.53 mmol) and potassium carbonate (0.11 g, 0.80 mmol) were combined in methyl ethyl ketone (2 mL)/DMF (1 mL, 12.8) and heated in the microwave for 30 minutes at 180° C. The reaction mixture was diluted with DCM, washed with water, dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by basic prep HPLC (method 2) to afford 5-[2-[[2-(5-isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethyl]-2-oxa-5-azabicyclo[2.2.1]heptane as a colourless gum (20 mg). LCMS RT=4.33 min. M+1=415.

후처리

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by basic prep HPLC (method 2)

출처 및 근거

ORD 기록
ord-bae1a31b3aa443d5a16cfc27c3b41512
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09290511B2

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