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

HRID 842763

반응식

HRID 842763 반응식
[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

참가 물질

7

반응물 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

생성물 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

반응 조건

온도
30 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-21095a23d393418fbcba0e1d862ca66b
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376511B2

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