Diisopropylethylamine → N-(1-(5-Chloro-2-methoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine

HRID 1910551

반응식

HRID 1910551 반응식
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([CH3:12])(=[O:11])=[O:10].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH:20]([NH2:22])[CH3:21])[CH:19]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH:20]([NH:22][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[S:9]([CH3:12])(=[O:11])=[O:10])[CH3:21])[CH:19]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzeneHCID 45381491-(5-Chloro-2-methoxyphenyl)ethanamine

생성물 1

HCID 58707298N-(1-(5-Chloro-2-methoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine수율 35%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2,4-Difluoro-1-(methylsulfonyl)benzene (0.55 g, 2.9 mmol), 1-(5-chloro-2-methoxyphenyl)ethanamine (0.57 g, 2.9 mmol) and N,N-diisopropylethylamine (0.77 g, 5.9 mmol) were stirred at 65° C. in dry acetonitrile (20 mL) for 24 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and purified by silica chromatography in 20% ethyl acetate in hexanes to collect the title compound (0.36 mg, 35% yield). 1H NMR (400 MHz, CDCl3): δ 7.74 (q, 1H), 7.18 (m, 2H), 6.84 (d, 1H), 6.79 (d, 1H), 6.42 (t, 1H), 6.17 (d, 1H), 4.78 (m, 1H), 3.91 (s, 3H), 3.08 (s, 3H), 1.52 (d, 3H).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. custompurified by silica chromatography in 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-01b44a84cd314ba3befe4d24fa7ef62e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604021B2

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