Sodium Methoxide → HCID 11620207、化合物

HRID 502691ノート

反応式

HRID 502691 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13](F)=[C:14]([CH:34]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:16])=[CH:4][N:3]=1.[CH3:36][O-:37].[Na+]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([O:37][CH3:36])=[C:14]([CH:34]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:16])=[CH:4][N:3]=1

参加物

3

反応物 2

HCID 10942334Sodium MethoxideHCID 16109018HCID 16109018、化合物

生成物 1

HCID 11620207HCID 11620207、化合物

実験手順

A mixture of 5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluoro-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide (0.14 g, 0.29 mmol) and NaOMe (0.5 M solution in methanol, 2.0 mL, 1.0 mmol) in a sealed tube was heated to reflux. After 16 h, the reaction was cooled and partitioned between EtOAc and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The material was purified by preparative TLC, eluting with 30% acetone/dichloromethane to give 5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-methoxy-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide as a white solid. MS m/z=496 [M+H]+. Calc'd for C26H24F3N5O2: 495.

後処理

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was cooled
  3. custompartitioned between EtOAc and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by preparative TLC
  8. washeluting with 30% acetone/dichloromethane

出典と根拠

ORDレコード
ord-66778798aeb343859473d53584d8ea29
出典データセット
uspto-grants-2010_08
特許番号
US07776869B2

反応ノート

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