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

HRID 1880120노트

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HRID 1880120 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
140 °C

실험 절차

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) +++++.

후처리

  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

출처 및 근거

ORD 기록
ord-0b017bfb4b144e74a08c8560588ea05c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318718B2

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