6-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione → 6-[2-(5-Chloro-2,4-dimethoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-3-(2-methyl-1H-imidazol-4-ylmethyl)-5,6-dihydro-pyran-2-one

HRID 858728Notes

Reaction equation

HRID 858728 reaction equation
[Cl:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH2:8][CH2:9][C:10]2([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[O:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[CH2:11]2)[CH:7]=1.ClC1C=C(CCC2(C3CCCC3)OC(=O)CC(=O)C2)C=CC=1OC(C)C.[CH3:53][C:54]1[NH:55][CH:56]=[C:57]([CH:59]=O)[N:58]=1.CC1C=C(C)N2N=C(C=O)N=C2N=1>>[Cl:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH2:8][CH2:9][C:10]2([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[O:15][C:14](=[O:16])[C:13]([CH2:59][C:57]3[N:58]=[C:54]([CH3:53])[NH:55][CH:56]=3)=[C:12]([OH:17])[CH2:11]2)[CH:7]=1

Participants

5

Reactant 4

HCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dioneHCID 167287396-[2-(3-Chloro-4-isopropoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dioneHCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 178418999HCID 178418999, compound

Product 1

HCID 1784934446-[2-(5-Chloro-2,4-dimethoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-3-(2-methyl-1H-imidazol-4-ylmethyl)-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared analogously to Example B(31), where 6-[2-(5-Chloro-2,4-dimethoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione (described below), as substituted in place of 6-[2-(3-Chloro-4-isopropoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione and 2-methyl-1H-imidazole-4-carbaldehyde was substituted in place of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde of that example.

Sources & evidence

ORD record
ord-576a07a32bff4321bc30d2bdcd719fc6
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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