Diisopropylethylamine → (4-Benzyl-2,2,5,5-tetramethyl-piperazin-1-yl)-[6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone

HRID 2279140ノート

反応式

HRID 2279140 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([C:27]([OH:29])=O)[C:14]3[C:19]([CH3:20])=[N:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:15]=3[N:16]=2)=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.[CH2:39]([N:46]1[CH2:51][C:50]([CH3:53])([CH3:52])[NH:49][CH2:48][C:47]1([CH3:55])[CH3:54])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl.O>[CH2:39]([N:46]1[C:47]([CH3:55])([CH3:54])[CH2:48][N:49]([C:27]([C:13]2[CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=3)[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]=23)=[O:29])[C:50]([CH3:53])([CH3:52])[CH2:51]1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 308103HCID 308103、化合物HCID 900138076-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

生成物 1

HCID 90013965(4-Benzyl-2,2,5,5-tetramethyl-piperazin-1-yl)-[6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 1.24 g of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid in 15 ml of DCM were added 2.1 ml of Hünig's base, 1.03 g of BEP and 0.87 g of 1-Benzyl-2,2,5,5-tetramethyl-piperazine. The reaction was stirred at r.t. for 3 h. For workup it was diluted with water and DCM and the layers were separated. The organic layer was washed with water twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 1.54 g (81%) of the title compound.

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, heptane/EtOAc gradient)

出典と根拠

ORDレコード
ord-ae8886be63aa461fbb7aee87daac9488
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

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