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Tetrabutylammonium Fluoride → N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

HRID 607427
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HRID 607427 반응식
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:44])(=[O:43])=[N:17][C:18](=[O:42])[C:19]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]4[O:37][CH:38]=[CH:39][C:40]=4[CH3:41])=[O:35])[CH:28]=3)[CH:22]=[N:21][CH:20]=2)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:44])(=[O:43])=[N:17][C:18](=[O:42])[C:19]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]4[O:37][CH:38]=[CH:39][C:40]=4[CH3:41])=[O:35])[CH:28]=3)[CH:22]=[N:21][CH:20]=2)=[CH:12][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 57657965N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

생성물 1

HCID 57657893N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide수율 94%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran
용매
2회
HCID 8857Ethyl Acetate용매

실험 절차

N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide (0.722 g, 1.15 mmol) was dissolved in THF (2.3 mL). The resulting solution was treated with 1M solution of TBAF in THF (2.3 mL, 2.30 mmol) causing the mixture to turn black in color. The mixture was allowed to stir for 1 h, subsequently dissolved in EtOAc (10 mL) and extracted with H2O (3×15 mL). The organic layer was dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude product was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc) to afford the title compound in 94% yield (0.350 g, 0.682 mmol).

후처리

  1. extractionextracted with H2O (3×15 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4(s)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc)

출처 및 근거

ORD 기록
ord-eeee594599414b9285630070c5275b2b
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915443B2

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