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HCID 59140413, 화합물 → HCID 86637791, 화합물

HRID 425334
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HRID 425334 반응식
C([Li])CCC.[S:6]1[CH2:11][CH2:10][CH2:9][S:8][CH:7]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1.[CH3:24][C:25]([CH3:41])([CH3:40])[CH2:26][C:27]1[N:28]=[C:29]([CH:38]=[O:39])[N:30]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH:31]=1>O1CCCC1>[CH3:24][C:25]([CH3:41])([CH3:40])[CH2:26][C:27]1[N:28]=[C:29]([CH:38]([OH:39])[C:7]2([C:12]3[CH:13]=[CH:14][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[CH:16][CH:17]=3)[S:8][CH2:9][CH2:10][CH2:11][S:6]2)[N:30]([S:32]([N:35]([CH3:36])[CH3:37])(=[O:33])=[O:34])[CH:31]=1
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참가 물질

5

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HCID 59140413HCID 59140413, 화합물2회HCID 86637792HCID 86637792, 화합물HCID 178418339Butyllithium

생성물 1

HCID 86637791HCID 86637791, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

n-Butyllithium (2.5 M in hexane) (0.14 mL, 0.17 mol) was added to a −78° C. solution of 2-[4-(1,3-dithian-2-yl)phenyl]pyridine (50 mg, 0.18 mmol) in tetrahydrofuran (3 mL). After stirring at 0° C. for 10 min, the reaction mixture was re-cooled to −78° C. and a solution of 4-(2,2-dimethylpropyl)-2-formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide (intermediate 13) (100 mg, 0.37 mmol) in tetrahydrofuran (1 mL) was added. After stirring at −78° C. for 5 min then at ambient temperature for a further 10 min, the reaction mixture was quenched with water and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparative plate chromatography eluting with 50% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-{hydroxy[2-(4-pyridin-2-ylphenyl)-1,3-dithian-2-yl]methyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

후처리

  1. temperaturethe reaction mixture was re-cooled to −78° C.
  2. stirringAfter stirring at −78° C. for 5 min
  3. waitat ambient temperature for a further 10 min
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. washPreparative plate chromatography eluting with 50% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-a8dc27af38834de2b012b15db3e449b8
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106070B2

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