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

HRID 17441

반응식

HRID 17441 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-9ec769c0139b4e329d8195eb0943cdaf
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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