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Pyridinium chloride → 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile

HRID 2213824
ノート
印刷プレビュー

反応式

HRID 2213824 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([O:16][CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:13]([O:25][CH3:26])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:27]#[N:28].[Cl:29][C:30]1[CH:31]=[C:32]([NH2:43])[CH:33]=[CH:34][C:35]=1[S:36][C:37]1[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=1.Cl.N1C=CC=CC=1>C(OCCO)C.CCOCC>[Cl:29][C:30]1[CH:31]=[C:32]([NH:43][C:2]2[C:11]3[C:6](=[CH:7][C:8]4[CH:15]=[C:14]([O:16][CH2:17][CH2:18][N:19]5[CH2:20][CH2:21][O:22][CH2:23][CH2:24]5)[C:13]([O:25][CH3:26])=[CH:12][C:9]=4[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:27]#[N:28])[CH:33]=[CH:34][C:35]=1[S:36][C:37]1[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=1
参加物反応条件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 10176127Pyridinium chlorideHCID 114590883-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamineHCID 120627424-Chloro-7-methoxy-8-(2-morpholin-4-yl ethoxy)benzo[g]quinoline-3-carbonitrile

生成物 1

HCID 101454084-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile収率 59.1%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 8076Glycol monoethyl ether溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1.98 g (4.98 mmol) of 4-chloro-7-methoxy-8-(2-morpholin-4-yl ethoxy)benzo[g]quinoline-3-carbonitrile, 1.31 g (5.47 mmol) of 3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine and 0.6 g (5.2 mmol) of pyridine hydrochloride in 2-ethoxyethanol is heated at 120° C. for 1.25 hours, then cooled. The crude mixture is poured into a solution of saturated sodium bicarbonate/ice and stirred for 45 minutes. The resulting solid is collected by filtration, then washed with water, ether and ethyl acetate successively. After drying in vacuo, the solid is purified by silica gel chromatography, using a 94:6 to 9:1 gradient of methylene chloride/methanol to provide a yellow solid. This solid is suspended in ether, filtered, and further washed with ether. After drying in vacuo, 1.77 g of 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile is obtained as a yellow solid, mp. >300° C.

後処理

  1. temperaturecooled
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with water, ether and ethyl acetate successively
  4. customAfter drying in vacuo
  5. customthe solid is purified by silica gel chromatography
  6. customto provide a yellow solid
  7. filtrationfiltered
  8. washfurther washed with ether
  9. customAfter drying in vacuo

出典と根拠

ORDレコード
ord-04ef6761fd124661a4653ae80ee20197
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07105531B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート