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Methyl iodide → N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-N-methyl-butyramide

HRID 1927615
ノート
印刷プレビュー

反応式

HRID 1927615 の反応式
[CH2:1]([N:3]([CH2:34][CH3:35])[C:4]([CH:6]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:15][C:14]=2[F:27])[CH2:9][CH2:8]1)=[O:5])[CH3:2].[H-].[Na+].[CH3:38]I>CN(C=O)C.O>[CH2:34]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[N:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:38])[C:20](=[O:26])[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:15][C:14]=2[F:27])[CH2:11][CH2:12]1)=[O:5])[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 16666511N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramide

生成物 1

HCID 16665202N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-N-methyl-butyramide収率 50.3%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-{4-[4-(diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramide (48 mg, 0.10 mmol) in DMF (2 mL) was treated with NaH (60% in mineral oil; 5 mg, 0.12 mmol). After 10 min, MeI (7 μL, 0.12 mmol) was added. After 3 h, the mixture was diluted with water and extracted with DCM. The organic layer was concentrated to give an oil, which was purified by PTLC to give an off white solid (25 mg, 50%). MS (ESI): mass calcd. for C29H41FN4O2, 496.96. m/z found, 497.5 [M+H]+. 1H NMR (CDCl3): 7.49-7.46 (m, 2H), 7.40-7.32 (m, 3H), 6.93-6.89 (m, 1H), 6.87-6.81 (m, 2H), 4.37 (s, 1H), 3.51-3.47 (m, 1H), 3.45-3.40 (m, 1H), 3.33-3.25 (m, 1H), 3.24 (s, 3H), 3.19-3.16 (m, 5H), 2.75-2.70 (m, 4H), 2.23-2.19 (m, 1H), 1.63-1.56 (m, 2H), 1.41-1.33 (m, 2H), 1.12-1.05 (m, 6H), 0.81 (t, J=7.4, 6H).

後処理

  1. waitAfter 3 h
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated
  4. customto give an oil, which
  5. customwas purified by PTLC

出典と根拠

ORDレコード
ord-d1556254adb94b2aaf59e131b339be3c
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08183239B2

反応ノート

読み込み中…

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