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

HRID 2237064

Reaction equation

[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]

Participants

Reactant 6

HCID 795Imidazole

HCID 1176Urea

HCID 61186Valeryl chloride

HCID 79057Carbonyl bromide

HCID 27772531-(4-(4-Methoxyphenoxy)phenyl)ethan-1-one

HCID 22061016tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

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

Procedure

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)

Workup

customThe BOC group of the product was removed

Sources & evidence

ORD record: ord-3f22503a2e4643e79fa627d0fb889e26
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714013B2

Linked notes

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