Acetyl chloride → HCID 66926924、化合物

HRID 81066ノート

反応式

HRID 81066 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:19]=[C:18]([Cl:20])[C:15]([C:16]#[N:17])=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)[N:13]=2)=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C>ClCCl>[Cl:20][C:18]1[C:15]([C:16]#[N:17])=[C:14]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:23][CH:22]=2)[N:13]=[C:12]([C:9]2[CH:8]=[CH:7][C:6]([NH:5][C:1](=[O:3])[CH3:2])=[CH:11][CH:10]=2)[CH:19]=1

参加物

5

反応物 3

HCID 6367Acetyl chloride2 回HCID 81531DiisopropylethylamineHCID 669269446-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile

生成物 1

HCID 66926924HCID 66926924、化合物収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Acetyl chloride (0.013 mL, 0.181 mmol) was added to a suspension of 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile (48 mg, 0.121 mmol, from Step 3 of Example 199) and Hunig's base (0.084 mL, 0.483 mmol) in dichloromethane (1 mL) at room temperature. After 90 min at room temperature, additional acetyl chloride (0.05 mL) was added. After additional 23 h, the reaction was stopped and the mixture purified by silica gel chromatography, eluting with 0-60% ethyl acetate in hexanes, to give N-(4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)phenyl)acetamide as yellow solid (24.9 mg, 47% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (2H, δ, J=8.78 Hz), 8.00-8.03 (2H, m), 7.79 (1H, s), 7.68 (2H, δ, J=8.53 Hz), 7.35-7.44 (3H, m), 7.19 (1H, t, J=7.40 Hz), 7.08-7.15 (4H, m), 2.23 (3H, s); MS (ES+) m/z: 440 (M+H); LC retention time: 4.668 min (analytical HPLC Method A). Unreacted starting material was also recovered (13.7 mg).

後処理

  1. waitAfter additional 23 h
  2. customthe mixture purified by silica gel chromatography
  3. washeluting with 0-60% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-ba4295629efc40678e010190f2af391d
出典データセット
uspto-grants-2014_09
特許番号
US08846673B2

反応ノート

読み込み中…