Imidazole → 7-{2-Butyl-4-[4-(4-methoxy-phenoxy)-phenyl]-imidazol-1-yl}-1,2,3,4-tetrahydro-isoquinoline hydrochloride

HRID 17741

Reaktionsgleichung

Reaktionsgleichung von HRID 17741
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=O)[CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.BrC(Br)=O.[NH2:23][C:24]1[CH:33]=[C:32]2[C:27]([CH2:28][CH2:29][N:30](C(OC(C)(C)C)=O)[CH2:31]2)=[CH:26][CH:25]=1.N[C:42]([NH2:44])=O.[C:45]([Cl:51])(=O)[CH2:46][CH2:47][CH2:48]C.N1C=CN=C1>>[ClH:51].[CH2:45]([C:42]1[N:23]([C:24]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][NH:30][CH2:31]3)=[CH:26][CH:25]=2)[CH:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:6]3[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:9][CH:10]=2)[N:44]=1)[CH2:46][CH2:47][CH3:48]

Komponenten

7

Edukt 6

HCID 795ImidazoleHCID 1176UreaHCID 61186Valeryl chlorideHCID 79057Carbonyl bromideHCID 27772531-(4-(4-Methoxyphenoxy)phenyl)ethan-1-oneHCID 22061016tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate

Produkt 1

HCID 669775357-{2-Butyl-4-[4-(4-methoxy-phenoxy)-phenyl]-imidazol-1-yl}-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Versuchsvorschrift

1-[4-(4-methoxyphenoxy)phenyl]ethan-1-one (1 mmol) was brominated by General Procedure R1. The bromo ketone was condensed with 7-amino-2-Boc-1,2,3,4-tetrahydroisoquinoline following general procedure R2. The aminoketone intermediate was treated with n-pentanoyl chloride accoding to General Procedure R3. The product amide was then subjected to imidazole formation employing general procedure R4. The BOC group of the product was removed employing general procedure T1 to afford 7-{2-butyl-4-[4-(4-methoxy-phenoxy)-phenyl]-imidazol-1-yl}-1,2,3,4-tetrahydro-isoquinoline hydrochloride (yield 135 mg)

Aufarbeitung

  1. customThe BOC group of the product was removed

Quellen und Nachweise

ORD-Eintrag
ord-f2ab40e73e5c4a46b8f5db2675ce8fd1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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