4-Hydroxymethylpyridine → N-isobutyl-N-(6-methoxypyridin-2-yl)-4-(pyridin-4-ylmethoxy)benzenesulfonamide

HRID 594156노트

반응식

HRID 594156 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[H-].[Na+]>CN(C)C=O>[CH2:28]([N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=1)[S:16]([C:13]1[CH:14]=[CH:15][C:10]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH:29]([CH3:31])[CH3:30]

참가 물질

5

반응물 3

HCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 898763574-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide

생성물 1

HCID 72194422N-isobutyl-N-(6-methoxypyridin-2-yl)-4-(pyridin-4-ylmethoxy)benzenesulfonamide수율 26.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Pyridin-4-ylmethanol (20.22 mg, 0.185 mmol) and 4-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide (62.7 mg, 0.185 mmol) were dissolved in N,N-dimethylformamide (DMF) (3 mL) and sodium hydride (7.41 mg, 0.185 mmol, 60% wt in mineral oil) added. Reaction left to stir at room temperature, under nitrogen, for 3 hours. The reaction was then quenched by adding water (2 mL). The mixture was concentrated in vacuo and the product extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was dried by passing it through a hydrophobic frit, concentrated and then purified by mass directed autoprep (formic acid modifier), to give the title compound (21.2 mg). LCMS (2 min, formic) Rt 1.05 min, m/z (ES+) 428 (M+H).

후처리

  1. customReaction
  2. waitleft
  3. customThe reaction was then quenched
  4. additionby adding water (2 mL)
  5. concentrationThe mixture was concentrated in vacuo
  6. extractionthe product extracted to the organic phase of an aqueous work up between ethyl acetate and water
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. custompurified by mass

출처 및 근거

ORD 기록
ord-be83ba92e3ba4af4a1704e5deb9d6574
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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