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Trifluoroacetic acid → 5-{1-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid amide

HRID 1928251
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HRID 1928251 반응식
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:15]=[CH:16][N:17]([C:19]3[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([CH3:32])[CH:26]=4)[CH:22]=[C:21]([CH3:33])[N:20]=3)[CH:18]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[CH:22]=[C:21]([CH3:33])[N:20]=[C:19]([N:17]3[CH:18]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[N:15]=[CH:16]3)[N:24]=2)=[CH:26][C:27]=1[CH3:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 602094505-{1-[4-(4-chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide

생성물 1

HCID 574689975-{1-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid amide수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled and stirred solution of 5-{1-[4-(4-chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide (0.54 g) in dichloromethane (5 ml) was added TFA (5 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness and saturated NaHCO3 solution (10 ml) was added. The mixture was stirred at room temperature for 30 min, the precipitate was collected by filtration and washed with water. The crude product was further purified by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (THF/diethyl ether) to yield the title compound as a white solid (0.24 g, 52%). MS (ISP) 445.9 [(M+H)+]; mp 267° C. (dec.).

후처리

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (10 ml)
  3. additionwas added
  4. stirringThe mixture was stirred at room temperature for 30 min
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customThe crude product was further purified by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (THF/diethyl ether)

출처 및 근거

ORD 기록
ord-84028d4c240c4d08a3499262ac82ad4e
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183262B2

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