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Phosphate → 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-1-(3,4-dichlorobenzoyl)indoline-7-carbonitrile

HRID 273857
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 273857
[C:1]([O:5][C:6]([N:8]([CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH2:34][CH3:35])[CH:9]([CH3:23])[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20]([NH2:22])=O)[CH:19]=1)[NH:16][CH2:15][CH2:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:40](Cl)=[O:41].P([O-])([O-])([O-])=O>C(Cl)Cl.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]([CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH2:34][CH3:35])[CH:9]([CH3:23])[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20]#[N:22])[CH:19]=1)[N:16]([C:40](=[O:41])[C:39]1[CH:43]=[CH:44][C:45]([Cl:46])=[C:37]([Cl:36])[CH:38]=1)[CH2:15][CH2:14]2)=[O:7])([CH3:3])([CH3:4])[CH3:2]
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Komponenten

6

Edukt 3

HCID 1061PhosphateHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 200943485-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide

Produkt 1

HCID 200943775-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-1-(3,4-dichlorobenzoyl)indoline-7-carbonitrileAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049
Pyridine
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide (97 mg) in methylene chloride (1 ml) and pyridine (1 ml) was added 3,4-dichlorobenzoyl chloride (84 mg), and the mixture was stirred at room temperature for 20 hours. The pH of the reaction mixture was adjusted to pH 7 with phosphate buffer solution, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and ethyl acetate (4/1) as eluent to give 98 mg of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-1-(3,4-dichlorobenzoyl)indoline-7-carbonitrile as an oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  6. additiona mixture of hexane and ethyl acetate (4/1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-6361d82db16f4a659f1ff38f8beabe81
Quelldatensatz
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05387603

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