Hydrogen Peroxide → 2-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzamide

HRID 1877475ノート

反応式

HRID 1877475 の反応式
C(=O)([O-])[O-:2].[K+].[K+].[NH2:7][CH2:8][CH2:9][CH2:10][OH:11].F[C:13]1[CH:20]=[C:19]([N:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([C:34]4[CH:35]=[N:36][CH:37]=[C:38]([O:40][CH3:41])[CH:39]=4)[C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].[OH-].[Na+].OO>CS(C)=O.O.C(O)C>[OH:11][CH2:10][CH2:9][CH2:8][NH:7][C:13]1[CH:20]=[C:19]([N:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([C:34]4[CH:35]=[N:36][CH:37]=[C:38]([O:40][CH3:41])[CH:39]=4)[C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:14]=1[C:15]([NH2:16])=[O:2]

参加物

9

反応物 5

HCID 784Hydrogen PeroxideHCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 673080012-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile

生成物 1

HCID 583382602-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzamide

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

0.85 g of potassium carbonate and 3.14 ml of 3-amino-1-propanol are successively added to a solution of 0.81 g of 2-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile obtained in stage 2 of Example 27, in 7 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 1 hour and 20 minutes in a microwave, and then 20.9 ml of ethanol are added, followed by 4 ml of a 1N solution of sodium hydroxide and 4 ml of 30% aqueous hydrogen peroxide. The reaction mixture is stirred at ambient temperature for 2 hours and then diluted with distilled water. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with water and a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The white solid obtained is purified by trituration in diisopropyl ether, so as to give 0.45 g of 2-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzamide in the form of a white solid, the characteristics of which are the following:

後処理

  1. extractionThe aqueous phase is extracted twice with ethyl acetate
  2. washthe combined organic phases are washed with water
  3. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe white solid obtained
  6. customis purified by trituration in diisopropyl ether

出典と根拠

ORDレコード
ord-7a2d93c0b66d446489f46204ffd507e2
出典データセット
uspto-grants-2012_11
特許番号
US08309721B2

反応ノート

読み込み中…