Cesium carbonate → 4-cyano-7-fluoro-N,N,5-trimethyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-2-carboxamide

HRID 17396

반응식

HRID 17396 반응식
Br[CH2:2][C:3]([C:5]1[C:18]([CH3:19])=[C:17]([C:20]#[N:21])[C:8]2[N:9]=[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]=1[F:22])=O.[C:23]([NH2:26])(=[S:25])[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[C:20]([C:17]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]([F:22])=[C:5]([C:3]2[N:26]=[C:23]([CH3:24])[S:25][CH:2]=2)[C:18]=1[CH3:19])#[N:21]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2723949ThioacetamideHCID 866308456-Bromoacetyl-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

생성물 1

HCID 685848584-cyano-7-fluoro-N,N,5-trimethyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-2-carboxamide수율 65.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

Under nitrogen atmosphere, a toluene (100 ml) suspension of 6-bromoacetyl-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide (I-128) (3.80 g, 10.3 mmol), thioacetamide (931 mg, 12.4 mmol) and cesium carbonate (4.36 g, 13.4 mmol) was stirred at 100° C. for 45 minutes. After cooling, the reaction liquid was filtered through Celite, the obtained filtrate was washed with water and saturated brine. Next, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica, gel column chromatography, and the eluate with n-hexane/ethyl acetate (1:1, v/v) gave the entitled compound (2.31 g, 65%) as a yellow solid.

후처리

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. filtrationwas filtered through Celite
  4. washthe obtained filtrate was washed with water and saturated brine
  5. dry with materialNext, the organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-50945d146f144516ad8a370e03d000f9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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