Tetrabutylammonium Fluoride → 4-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 361424노트

반응식

HRID 361424 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][C:30]=2[S:35]([N:38]([C:47]2[C:52]([O:53][CH3:54])=[N:51][C:50]([CH3:55])=[CH:49][N:48]=2)COCC[Si](C)(C)C)(=[O:37])=[O:36])=[CH:25][CH:24]=1)[CH:20]([CH3:22])[CH3:21]>C1COCC1.O>[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][C:30]=2[S:35]([NH:38][C:47]2[C:52]([O:53][CH3:54])=[N:51][C:50]([CH3:55])=[CH:49][N:48]=2)(=[O:37])=[O:36])=[CH:25][CH:24]=1)[CH:20]([CH3:22])[CH3:21]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium Fluoride2회HCID 211862384-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide

생성물 1

HCID 211862424-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide수율 9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Tetrabutylammonium fluoride (0.45 ml of a 1.0M solution in THF) was added to a solution of 4-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide (0.205 g) in dry THF (2 ml) and the solution was heated under reflux for 40 minutes. More tetrabutylammonium fluoride solution (0.95 ml) was added and heating was continued for 2 hours. The reaction mixture was diluted with water (15 ml) and extracted with ether (2×30 ml). The organic extracts were washed with water and saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 40-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane to give 4-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.014 g), m.p. 232°-233° C.; 1H NMR (d6 -DMSO): 0.9 (d, 6 H), 1.8 (br m, 1 H), 2.1-2.5 (br m, 5 H), 3.8 (s, 3 H), 7.1-7.3 (m, 4 H), 7.35 (d, 1 H), 7.5 (s, 1 H), 8.75 (d, 1 H), 9.1 (s, 1 H), 10.4 (s, 1 H); mass spectrum (+ve ESP): 413 (M+H)+.

후처리

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 40 minutes
  3. temperatureheating
  4. extractionextracted with ether (2×30 ml)
  5. washThe organic extracts were washed with water and saturated sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified by gradient elution with 40-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column
  9. customfollowed by recrystallisation from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-d92cbe5fa1454bb2a3d263cf2e16546a
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866568

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