Triethylamine → Ethyl 6-bromo-1-{2-[(methylsulfonyl)oxy]ethyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047148노트

반응식

HRID 1047148 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:12][CH2:13][OH:14])[CH:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2=[O:20].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:12][CH2:13][O:14][S:29]([CH3:28])(=[O:31])=[O:30])[CH:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2=[O:20]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68746778Ethyl 6-bromo-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate2회

생성물 1

HCID 86665044Ethyl 6-bromo-1-{2-[(methylsulfonyl)oxy]ethyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of ethyl 6-bromo-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 17, 800 mg, 2.34 mmol) and triethylamine (473 mg, 4.69 mmol) in dichloromethane (50 mL) was cooled to 0° C. and methane sulphonyl chloride (400 mg, 3.50 mmol) was added drop wise. The mixture was allowed to stir at room temperature for 3 h. The reaction mixture was washed with water and the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 700 mg, (71%) of ethyl 6-bromo-1-{2-[(methylsulfonyl)oxy]ethyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, which was taken without further purification to next step.

후처리

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4997c6bd31334f6ea6c1a0cbad12bf60
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569484B2

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