Diisopropylethylamine → 1-(3-(1-(5-chloro-2,3-dimethoxyphenyl)ethylamino)-4-(methylsulfonyl)phenyl)-N,N-dimethylpiperidin-4-amine

HRID 2426075노트

반응식

HRID 2426075 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([O:24][CH3:25])[C:5]([O:22][CH3:23])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15](F)[CH:14]=[CH:13][C:12]=2[S:18]([CH3:21])(=[O:20])=[O:19])[CH3:9])[CH:7]=1.[CH3:26][N:27]([CH3:34])[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:24][CH3:25])[C:5]([O:22][CH3:23])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:31]3[CH2:32][CH2:33][CH:28]([N:27]([CH3:34])[CH3:26])[CH2:29][CH2:30]3)[CH:14]=[CH:13][C:12]=2[S:18]([CH3:21])(=[O:20])=[O:19])[CH3:9])[CH:7]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 44240863N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine

생성물 1

HCID 587072651-(3-(1-(5-chloro-2,3-dimethoxyphenyl)ethylamino)-4-(methylsulfonyl)phenyl)-N,N-dimethylpiperidin-4-amine수율 19.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine (100.0 mg, 0.26 mmol), N,N-dimethylpiperidin-4-amine (66.0 mg, 0.51 mmol), N,N-diisopropylethylamine (133.0 mg, 1.03 mmol) were stirred at 100° C. in dry acetonitrile (3 mL) for 16 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and the crude compound was purified by silica chromatography using 10% methanol in dichloromethane to afford the title compound (25.0 mg, 19.6% yield). 1H NMR (400 MHz, CDCl3): δ 7.53 (d, 1H), 6.88 (d, 1H), 6.78 (d, 1H), 6.50 (d, 1H), 6.21 (d, 1H), 5.90 (d, 1H), 4.85 (m, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 3.74 (m, 2H), 3.24 (m, 1H), 3.05 (s, 3H), 2.76 (q, 2H), 2.26 (s, 6H), 1.78 (t, 2H), 1.55 (d, 3H), 1.45 (m, 2H); MS (ESI) m/z: 496.1 (M+).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. customthe crude compound was purified by silica chromatography

출처 및 근거

ORD 기록
ord-29806359d6034fd797226b81910d51e6
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968538B2

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