4-chloro-6-hydrazinyl-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt → HCID 86665693、化合物

HRID 81055ノート

反応式

HRID 81055 の反応式
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[Cl:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[N:12]=[C:11](NN)[C:10]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>S([O-])([O-])(=O)=O.[Cu+2].C(O)CC>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[Cl:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)[N:12]=[CH:11][C:10]=1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

4

反応物 1

HCID 866656944-chloro-6-hydrazinyl-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt

生成物 1

HCID 86665693HCID 86665693、化合物収率 26.1%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 10311-Propanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-chloro-6-hydrazinyl-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt (72.6 mg, 0.138 mmol), 1.0 M aqueous copper(II) sulfate (0.276 mL, 0.276 mmol) and 1-propanol (1 mL) was heated to 100° C. in a sealed tube for 2 h. After cooling to room temperature, the mixture was filtered. The filtrate was concentrated and purified by reverse phase HPLC (isocratic 100% solvent B for 25 min, 40 mL/min, Sunfire 30×250 mm to give 4-chloro-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt as white solid (17.9 mg, 26% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.78 (1H, s), 7.87-7.96 (2H, m), 7.46-7.56 (5H, m), 7.37-7.45 (2H, m), 7.20 (1H, t, J=7.40 Hz), 7.09-7.17 (4H, m); MS (ES+) m/z: 383 (M+H); LC retention time: 4.790 min (analytical HPLC Method A).

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. custompurified by reverse phase HPLC (isocratic 100% solvent B for 25 min

出典と根拠

ORDレコード
ord-4ded2ca8572d485e80e7e18ffcd8359f
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…