Cesium carbonate → HCID 59374125、化合物

HRID 473671ノート

反応式

HRID 473671 の反応式
F[C:2]1[C:7]([CH:8]2[CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.O>[O:11]1[CH2:12][CH2:13][CH2:14][CH:8]([C:7]2[C:2]([O:28][C:25]3[CH:24]=[CH:23][C:22]([NH:21][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=4)=[CH:27][CH:26]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 212625714-(Pyridin-2-ylamino)phenolHCID 59327121HCID 59327121、化合物

生成物 1

HCID 59374125HCID 59374125、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

2-Fluoro-3-(oxepan-4-yl)pyridine (0.061 g, 0.31 mmol), 4-(pyridin-2-ylamino)phenol (0.18 g, 0.94 mmol), and cesium carbonate (0.31 g, 0.94 mmol) were mixed in NMP (0.75 mL). The reaction mixture was placed under a nitrogen atmosphere and stirred at 120° C. for 17 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic layers were washed with 1 M aqueous sodium hydroxide, washed with sat. sodium chloride, dried over magnesium sulfate, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography to give N-(4-(3-(oxepan-4-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine MS (ESI, pos. ion) m/z: 362.2 (M+1). IC50 (uM) 0.026.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with 1 M aqueous sodium hydroxide
  4. washwashed with sat. sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-08b5f15b41ee4fcc8fc0342d34fa69f4
出典データセット
uspto-grants-2014_01
特許番号
US08637500B2

反応ノート

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