2-Amino-5-chlorobenzophenone → 4-[1-[(6-Chloro-2-methyl-4-phenyl-3-quinolinyl)carbonyl]-4-piperidinyl]benzamide

HRID 1184026ノート

反応式

HRID 1184026 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.O=[C:18]([CH3:37])[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:36]=[CH:35][C:31]([C:32]([NH2:34])=[O:33])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)=[O:21].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(O)C>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:18]([CH3:37])[C:19]([C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH2:34])=[O:33])=[CH:35][CH:36]=3)[CH2:24][CH2:23]1)=[O:21])=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 128702-Amino-5-chlorobenzophenoneHCID 2733225Ytterbium triflateHCID 86641821HCID 86641821、化合物

生成物 1

HCID 462149014-[1-[(6-Chloro-2-methyl-4-phenyl-3-quinolinyl)carbonyl]-4-piperidinyl]benzamide収率 76%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
82 °C

実験手順

To a solution of (2-amino-5-chlorophenyl)(phenyl)methanone (693 mg, 3.0 mmol) in ethanol (10 ml) was added 4-(1-(3-oxobutanoyl)piperidin-4-yl)benzamide (893 mg, 3.1 mmol) followed by ytterbium triflate (186 mg, 0.3 mmol). The mixture was heated at 82° C. for 12 hours. The reaction mixture was cooled to room temperature, and the white powder thus obtained was filtered off, washed with ethanol, ethyl acetate, and finally ether to provide 4-(1-(6-chloro-2-methyl-4-phenylquinoline-3-carbonyl)piperidin-4-yl)benzamide (1.1 g, 76%) as a free flowing white powder. 1H NMR (DMSO-d6, 400 MHz) δ: 1 Rotameric forms complicates spectrum, the major rotamer is described; δ 8.09 (d, 1H, J=8.9 Hz); 7.9 (bs, NH, 1H); 7.8 (m, 3H); 7.7-7.5 (m, 6H); 7.25 (bs, NH, 1H); 6.8 (app d, 2H); 4.5 (d, 1H, J=12.9 Hz); 3.4-3.3 (m, 1H); 3.38 (s, 3H); 3.13 (app t, 1H, J=12.9 Hz); 2.8-2.4 (m, 2H); 2.5 (s, 3H); 0.72 (m, 1H); 0.54 (m, 1H). LC MS (CI) shows M+H 484.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe white powder thus obtained
  3. filtrationwas filtered off
  4. washwashed with ethanol, ethyl acetate, and finally ether

出典と根拠

ORDレコード
ord-47a5c2eb7d544a3a9601eb6aad8f238c
出典データセット
uspto-grants-2014_03
特許番号
US08664399B2

反応ノート

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