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6-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole → HCID 58541623, 화합물

HRID 600258
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HRID 600258 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18](SC)[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1.F[C:25]1C=CC(C2N=C3N(C=2)C=CS3)=CC=1.O[O:40][S:41]([O-:43])=O.[K+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([S:41]([CH3:25])(=[O:43])=[O:40])[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 8681986-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazoleHCID 23707502Potassium hydroxy sulfiteHCID 58541696HCID 58541696, 화합물

생성물 1

HCID 58541623HCID 58541623, 화합물수율 98%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water
용매

실험 절차

To a solution of the mixture (1.1:1) of 6-(4-fluorophenyl)-5-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (K) and 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (0.205 g, 0.6 mmol) in methanol (25 mL) is added drop-wise a solution of oxone (1.23 g, 1.8 mmol) in water (5 mL). The reaction is stirred at room temperature for 16 hours. The volatiles are removed in vacuo at room temperature. To the residue is added dichloromethane. The organic phase is washed sequentially with water and a saturated, aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography, eluting with ethyl acetate hexane (1:1) to yield 6-(4-fluorophenyl)-5-(2-methanesulfonyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (L) (Compound CXL, Table 2) as a white solid (0.113 g, 98%); m.p. 197-198° C.;

후처리

  1. customThe volatiles are removed in vacuo at room temperature
  2. additionTo the residue is added dichloromethane
  3. washThe organic phase is washed sequentially with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe crude product is purified by silica gel column chromatography
  8. washeluting with ethyl acetate hexane (1:1)

출처 및 근거

ORD 기록
ord-7aaf4a69822e4ba4bc95766f383be490
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902192B2

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