Acetic Acid → 5-[3,4-Dichlorophenoxy]-6-methoxy-8-[4-phthalimido-1-methyl-butylamino]lepidine

HRID 842763

反応式

HRID 842763 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([O:22][CH3:23])[C:5]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].O=[C:25]([CH3:40])[CH2:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].[BH4-].[Na+].[OH-].[Na+].[C:45](O)(=O)C>>[Cl:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[Cl:20])[O:13][C:5]1[C:4]([O:22][CH3:23])=[CH:3][C:2]([NH:1][CH:25]([CH3:40])[CH2:26][CH2:27][CH2:28][N:29]2[C:33](=[O:34])[C:32]3=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]3[C:30]2=[O:39])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH2:9][N:10]2[CH3:45].[Cl:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[Cl:20])[O:13][C:5]1[C:4]([O:22][CH3:23])=[CH:3][C:2]([NH:1][CH:25]([CH3:40])[CH2:26][CH2:27][CH2:28][N:29]2[C:33](=[O:34])[C:32]3=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]3[C:30]2=[O:39])=[C:11]2[C:6]=1[C:7]([CH3:12])=[CH:8][CH:9]=[N:10]2

参加物

7

反応物 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2362702-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dioneHCID 6090148-Amino-5-[3,4-dichlorophenoxy]-6-methoxylepidineHCID 4311764Sodium borohydride

生成物 2

HCID 6331175-[3,4-Dichlorophenoxy]-6-methoxy-8-[4-phthalimido-1-methyl-butylamino]lepidineHCID 694641975-(3,4-Dichlorophenoxy)-6-methoxy-1methyl-8-[(4-phthalimido-1-methylbutyl)amino]quinoline

反応条件

温度
30 °C

実験手順

A mixture of 12.4 g of 8-amino-5-(3,4-dichlorophenoxy)-6-methoxy-4-methylquinoline (36 mM) and 11.6 g of 4-oxo-1-phthalimidopentane (50 mM), in glacial acetic acid was stirred for 15 min under nitrogen and 2.6 g of sodium borohydride (70 mM) was added portionwise maintaining the temperature 25-35° C. After the addition, the reaction mixture was stirred for 30 min and then poured into ice cold solution of concentrated sodium hydroxide. The resulting precipitate was filtered and chromatographed over silica gel. Elution with hexanes:ethyl acetate 90:10 yielded the expected product of 5-(3,4-dichlorophenoxy)-6-methoxy-4-methyl-8-[(4-phthalimido-1-methylbutyl)amino]quino line which was crystallized from ether to give 12.4 g (22 mM) of yellow crystalline product.

後処理

  1. additionAfter the addition
  2. filtrationThe resulting precipitate was filtered
  3. customchromatographed over silica gel
  4. washElution with hexanes:ethyl acetate 90:10

出典と根拠

ORDレコード
ord-21095a23d393418fbcba0e1d862ca66b
出典データセット
uspto-grants-2002_04
特許番号
US06376511B2

関連ノート

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