4-Methoxybenzylamine → 3-[(1-Amino-5-isoquinolyl)oxy]propylamine hydrochloride

HRID 10502

Reaktionsgleichung

Reaktionsgleichung von HRID 10502
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[C:18]2[Cl:23])=O)(C)(C)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.COC1C=CC(C[NH2:52])=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[ClH:23].[NH2:52][C:18]1[C:19]2[C:14](=[C:13]([O:12][CH2:11][CH2:10][CH2:9][NH2:8])[CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:16][N:17]=1

Komponenten

8

Edukt 4

HCID 754524-MethoxybenzylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 21979957N-(tert-butoxycarbonyl)-3-[(1-chloro-5-isoquinolyl)oxy]propylamine2×HCID 23676156Sodium t-butoxide

Produkt 1

HCID 219798583-[(1-Amino-5-isoquinolyl)oxy]propylamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The title compound was synthesized from Intermediate 18 according to the method described in a reference (Buchwald, S. L., J. Org. Chem., 65, 1158 (2000)). That is, a suspension of Intermediate 18 (674 mg), tris (dibenzylideneacetone)dipalladium(0) (92 mg, Aldrich), 2-(di-tert-butylphosphino)biphenyl (119 mg, Strem Chemicals), 4-methoxybenzylamine (329 mg, Tokyo Kasei Kogyo) and sodium tert-butoxide (269 mg, Tokyo Kasei Kogyo) in toluene (5 ml) was stirred with heating at 80° C. under nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature and added with ethyl acetate (5 ml). The insoluble matters were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (525 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble matters were removed by filtration through Celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2e01521f8a6a49748b5268aa0846e201
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094789B2

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