Trifluoromethanesulfonic acid → 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

HRID 369034

반응식

HRID 369034 반응식
N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[F:14][C:15]([F:21])([F:20])[S:16]([OH:19])(=[O:18])=[O:17].N([O-])=O.[Na+]>O>[F:14][C:15]([F:21])([F:20])[S:16]([O:19][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:18])=[O:17]

참가 물질

5

반응물 3

HCID 62406Trifluoromethanesulfonic acidHCID 46725998-Methoxy-1,7-naphthyridin-6-amineHCID 23668193Sodium Nitrite

생성물 1

HCID 232846356-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a solution of 6-amino-8-methoxy-1,7-naphthyridine (19 g, 0.108 mol) in a 1:1 mixture of water and trifluoromethane sulfonic acid (380 ml) is carefully added a solution of sodium nitrite (11.2 g, 0.162 mol) in water (40 ml) at 0° C. After 1 h the cooling bath is removed and the reaction mixture stirred for an other hour at ambient temperature. Then, ethyl acetate (500 ml) is added and the solution is neutralized by adding sodium bicarbonate (4N, 1 l). The water phase is extracted again with ethyl acetate (3×500 ml). The organic solvent is evaporated and the crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone) affording the title compound. M+308; Melting point 99-101° C.

후처리

  1. customAfter 1 h the cooling bath is removed
  2. additionThen, ethyl acetate (500 ml) is added
  3. additionby adding sodium bicarbonate (4N, 1 l)
  4. extractionThe water phase is extracted again with ethyl acetate (3×500 ml)
  5. customThe organic solvent is evaporated
  6. customthe crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone)

출처 및 근거

ORD 기록
ord-0752721364024996b548b4ef802fbc9c
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136821

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