Cesium carbonate → 2-(Dimethylamino)-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17441

反応式

HRID 17441 の反応式
Br[CH2:2][C:3]([C:5]1[C:6]([F:20])=[C:7]2[O:11][C:10]([N:12]([CH3:14])[CH3:13])=[N:9][C:8]2=[C:15]([C:18]#[N:19])[C:16]=1[CH3:17])=O.[C:21]([NH2:24])(=[S:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:13][N:12]([CH3:14])[C:10]1[O:11][C:7]2[C:8](=[C:15]([C:18]#[N:19])[C:16]([CH3:17])=[C:5]([C:3]3[N:24]=[C:21]([CH3:22])[S:23][CH:2]=3)[C:6]=2[F:20])[N:9]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2723949ThioacetamideHCID 866308506-(Bromoacetyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685853432-(Dimethylamino)-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile収率 79%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

6-(Bromoacetyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-170) (0.60 g, 1.76 mmol) was dissolved in toluene (30 ml), then thioacetamide (0.16 g, 2.13 mmol) and cesium carbonate (0.75 g, 2.30 mmol) were added, followed by stirring at an external temperature of 100° C. for 16 hours. The reaction liquid was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to obtain a yellow solid (0.44 g, 79%).

後処理

  1. customThe reaction liquid
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

出典と根拠

ORDレコード
ord-9ec769c0139b4e329d8195eb0943cdaf
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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