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Cesium carbonate → 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cycloheptanone

HRID 1880118
ノート
印刷プレビュー

反応式

HRID 1880118 の反応式
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)=[O:17].F[C:26]1[C:31]([CH:32]2[CH2:38][CH2:37]N[C:35](=O)[CH2:34][CH2:33]2)=[CH:30][CH:29]=[CH:28][N:27]=1>CN1C(=O)CCC1>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:26]2[C:31]([CH:32]3[CH2:33][CH2:34][CH2:35][C:1](=[O:4])[CH2:37][CH2:38]3)=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:20][CH:19]=1)=[O:17]
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

5

反応物 3

HCID 10796Cesium carbonateHCID 593268345-(2-Fluoropyridin-3-yl)azepan-2-oneHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

生成物 1

HCID 593269804-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cycloheptanone

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

A mixture of cesium carbonate (0.24 g, 0.72 mmol), (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (0.17 g, 0.72 mmol), and 5-(2-fluoropyridin-3-yl)azepan-2-one (0.050 g, 0.24 mmol) in NMP (0.25 mL) under argon was heated to 140° C. for 36 h. After cooling to room temperature, the mixture was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with water several times, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by reversed phase HPLC, and the resulting oil was dissolved in DCM and washed with saturated aqueous sodium bicarbonate (2×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cycloheptanone. MS (ESI, pos. ion) m/z: 427.1 (M+1). IC50 (uM) +++++.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer was washed with water several times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil was purified by reversed phase HPLC
  9. dissolutionthe resulting oil was dissolved in DCM
  10. washwashed with saturated aqueous sodium bicarbonate (2×)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-402dd485f12a4dce9eb7852f40917a22
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318718B2

反応ノート

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