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

HRID 1910633ノート

反応式

HRID 1910633 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-ddd82255a7674c87b6a818c4570aecbf
出典データセット
uspto-grants-2013_12
特許番号
US08604021B2

反応ノート

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