4-Toluenesulfonyl chloride → 2-[[2-Fluoro-4-[[(2-methyl-1,8-naphthyridine-3-carbonyl)amino]methyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate

HRID 929373노트

반응식

HRID 929373 반응식
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[F:12][C:13]1[CH:14]=[C:15]([CH2:24][NH:25][C:26]([C:28]2[C:29]([CH3:38])=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][N:32]=3)=[O:27])[CH:16]=[CH:17][C:18]=1[CH2:19][O:20][CH2:21][CH2:22][OH:23].C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:8][C:7]1[CH:9]=[CH:10][C:4]([S:1]([O:23][CH2:22][CH2:21][O:20][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([CH2:24][NH:25][C:26]([C:28]3[C:29]([CH3:38])=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][N:32]=4)=[O:27])=[CH:14][C:13]=2[F:12])(=[O:3])=[O:2])=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 89647281HCID 89647281, 화합물

생성물 1

HCID 896472142-[[2-Fluoro-4-[[(2-methyl-1,8-naphthyridine-3-carbonyl)amino]methyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

25 mg tosylchloride (0.13 mmol) was added to a solution of 40 mg N-[[3-fluoro-4-(2-hydroxyethoxymethyl)phenyl]methyl]-2-methyl-1,8-naphthyridine-3-carboxamide (0.11 mmol), 23 μl diisopropylethylamine (6.13 mmol) and 13 mg DMAP (0.11 mmol) in 1.0 ml CH2Cl2 at room temperature. The solution was stirred for 2 h. The reaction mixture was placed directly on a SiO2 column and purified by flash chromatography (CH2Cl2/MeOH 50:1). Gave 52 mg (90%).

후처리

  1. custompurified by flash chromatography (CH2Cl2/MeOH 50:1)
  2. customGave 52 mg (90%)

출처 및 근거

ORD 기록
ord-1d79f9b126834bdcbf2b29e8a04c46f2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09295738B2

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