Water → 4-(2-(methylthio)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

HRID 2370490ノート

反応式

HRID 2370490 の反応式
[CH3:1][S:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:1][S:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 210778082-(Methylthio)benzo[d]oxazol-6-ol

生成物 1

HCID 577256324-(2-(methylthio)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

To a solution of 2-(methylthio)benzo[d]oxazol-6-ol (8.5 g, 46.7 mmol, 1 eq) in 80 mL of N,N-dimethylformamide was added 4-chloro-N-methylpyridine-2-carboxamide (16.0 g, 93.4 mmol, 2.0 eq) and cesium carbonate (45.7 g, 140.1 mmol, 3.0 eq). The reaction mixture was stirred at 75° C. for 6 hours. After the mixture was cooled to room temperature, the mixture was added 120 mL of water. After filtration, the solid was purified by silica gel column eluted with ethyl acetate and hexane to give the titled compound. MH+=316.

後処理

  1. temperatureAfter the mixture was cooled to room temperature
  2. filtrationAfter filtration
  3. customthe solid was purified by silica gel column
  4. washeluted with ethyl acetate and hexane

出典と根拠

ORDレコード
ord-17de8d996f854b3db0130c1a32d5f189
出典データセット
uspto-grants-2014_04
特許番号
US08710048B2

反応ノート

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