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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
ノート
印刷プレビュー

反応式

HRID 928568 の反応式
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]
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

7

反応物 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

生成物 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
収率 17.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
180 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bae1a31b3aa443d5a16cfc27c3b41512
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290511B2

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