Cesium carbonate → 5-(2-(4-(1H-Benzo[D]imidazole-2-carbonyl)phenoxy)pyridin-3-YL)-1-methylazepan-2-one

HRID 1880120ノート

反応式

HRID 1880120 の反応式
C(=O)([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:36]([CH3:39])[C:35](=[O:40])[CH2:34][CH2:33]2)=[CH:30][CH:29]=[CH:28][N:27]=1>CN1CCCC1=O>[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[CH2:38][CH2:37][N:36]([CH3:39])[C:35](=[O:40])[CH2:34][CH2:33]3)=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:20][CH:19]=1)=[O:17]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanoneHCID 593270605-(2-Fluoropyridin-3-yl)-1-methylazepan-2-one

生成物 1

HCID 462147165-(2-(4-(1H-Benzo[D]imidazole-2-carbonyl)phenoxy)pyridin-3-YL)-1-methylazepan-2-one

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 (0.29 g, 0.88 mmol), (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (0.21 g, 0.878 mmol), and 5-(2-fluoropyridin-3-yl)-1-methylazepan-2-one (0.07 g, 0.29 mmol) in 1-methyl-2-pyrrolidinone (0.5 mL) under argon was heated to 140° C. for 48 h, then cooled to room temperature. The resulting mixture was partitioned between ethyl acetate and water, the layers were separated, and the organic layer was washed with 1N aqueous sodium hydroxide (2×), saturated aqueous sodium chloride (1×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The oil was purified by silica gel chromatography 5-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)-1-methylazepan-2-one. MS (ESI, pos. ion) m/z: 441.1 (M+1). IC50 (uM) +++++.

後処理

  1. temperaturecooled to room temperature
  2. customThe resulting mixture was partitioned between ethyl acetate and water
  3. customthe layers were separated
  4. washthe organic layer was washed with 1N aqueous sodium hydroxide (2×), saturated aqueous sodium chloride (1×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe oil was purified by silica gel chromatography 5-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)-1-methylazepan-2-one

出典と根拠

ORDレコード
ord-0b017bfb4b144e74a08c8560588ea05c
出典データセット
uspto-grants-2012_11
特許番号
US08318718B2

反応ノート

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