Chloride → HCID 66977502, compound

HRID 2237063Notes

Reaction equation

HRID 2237063 reaction equation
F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=O)[CH3:13])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[Cl:23][C:24]1[CH:43]=[CH:42][C:27]([O:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([C:39](=[O:41])[CH3:40])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1.BrC(Br)=O.[NH2:48][C:49]1[CH:58]=[C:57]2[C:52]([CH2:53][CH2:54][N:55](C(OC(C)(C)C)=O)[CH2:56]2)=[CH:51][CH:50]=1.NC(N)=O.[Cl-].N1[CH:75]=[CH:74][N:73]=C1>>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([O:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([C:39](=[O:41])[CH3:40])=[CH:31][CH:30]=2)=[CH:42][CH:43]=1.[ClH:15].[CH2:75]([C:74]1[N:48]([C:49]2[CH:58]=[C:57]3[C:52]([CH2:53][CH2:54][NH:55][CH2:56]3)=[CH:51][CH:50]=2)[CH:13]=[C:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([O:22][C:19]3[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=3)=[CH:3][CH:4]=2)[N:73]=1)[CH2:25][CH2:24][CH3:43]

Participants

10

Reactant 8

HCID 312ChlorideHCID 795ImidazoleHCID 1176UreaHCID 46844-ChlorophenolHCID 675681-(4-Fluoro-1-naphthyl)ethan-1-oneHCID 79057Carbonyl bromideHCID 22061016tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 66977636HCID 66977636, compound

Product 2

HCID 66977502HCID 66977502, compoundHCID 66977636HCID 66977636, compound

Procedure

4′-(4-chlorophenoxy)-1′-acetonaphthone was prepared from 4′-fluoro-1′-acetonaphthone and 4-chlorophenol following general procedure Q2. 4′-(4-chlorophenoxy)-1′-acetonaphthone was brominated following 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-penatnoyl 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-chloro-phenoxy)-naphthalen-1-yl]-imidazol-1-yl}-1,2,3,4-tetrahydro-isoquinoline hydrochloride.

Workup

  1. customThe BOC group of the product was removed

Sources & evidence

ORD record
ord-ccae1ad9081742e884a93badb4177d54
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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