Piperazine → PRX-07034 free base

HRID 1910576ノート

反応式

HRID 1910576 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.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]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:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]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 4837PiperazineHCID 81531DiisopropylethylamineHCID 44240863N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine

生成物 1

HCID 11532574PRX-07034 free base収率 3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of [1-(5-chloro-2,3-dimethoxy-phenyl)-ethyl]-(5-fluoro-2-methanesulfonyl-phenyl)-amine (0.52 g, 1.34 mmol), piperazine (0.23 g, 2.68 mmol) and N,N-diisopropylethylamine (0.47 mL, 2.68 mmol) in acetonitrile was stirred at 80° C. for 24 h. The reaction mixture was cooled down and concentrated under reduced pressure. The residue was taken up in dichloromethane, washed with water, dried and concentrated in vacuo to yield the crude residue which was purified by preparative TLC (0.5% NH4OH/9.5% methanol/dichloromethane) to afford [1-(5-chloro-2,3-dimethoxy-phenyl)-ethyl]-(2-methanesulfonyl-5-piperazin-1-yl-phenyl)-amine (17 mg, 3%). 1H NMR (400 MHz, CD3OD): δ 7.42 (d, 1H), 6.87 (m, 2H), 6.25 (dd, 1H), 5.90 (s, 1H), 4.87 (m, 1H), 3.85 (s, 1H), 3.81 (s, 1H), 3.05-3.2 (m, 4 H), 3.78 (m, 4H), 1.49 (d, 3H). MS (ESI) m/z: Calculated: 453.98; Observed: 454.4 (M+H+); 476.4 (M+Na+); 930.8 (2M+Na+). Mol. Wt.: 453.98 (C21H28ClN3O4S).

後処理

  1. temperatureThe reaction mixture was cooled down
  2. concentrationconcentrated under reduced pressure
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto yield the crude residue which
  7. customwas purified by preparative TLC (0.5% NH4OH/9.5% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-65ab863937e74a558571b9a81c7b8273
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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