5-(Chloromethyl)-3-ethyl-1,2,4-oxadiazole → 6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-3-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one

HRID 858743Notes

Reaction equation

HRID 858743 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][CH3:9])[N:4]=1.[Cl:10][C:11]1[C:12]([O:34][CH3:35])=[CH:13][C:14]([O:32][CH3:33])=[C:15]([CH2:17][CH2:18][C:19]2([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[O:24][C:23](=[O:25])[CH2:22][C:21](=[O:26])[CH2:20]2)[CH:16]=1>>[Cl:10][C:11]1[C:12]([O:34][CH3:35])=[CH:13][C:14]([O:32][CH3:33])=[C:15]([CH2:17][CH2:18][C:19]2([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[O:24][C:23](=[O:25])[C:22]([CH2:2][C:3]3[O:7][N:6]=[C:5]([CH2:8][CH3:9])[N:4]=3)=[C:21]([OH:26])[CH2:20]2)[CH:16]=1

Participants

3

Reactant 2

HCID 162279165-(Chloromethyl)-3-ethyl-1,2,4-oxadiazoleHCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione

Product 1

HCID 587626246-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-3-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-oneYield 7%

Procedure

The title compound was prepared as described in Example B(53), using 5-(chloromethyl)-3-ethyl-1,2,4-oxadiazole (Step 1, below) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 7%.

Sources & evidence

ORD record
ord-4a8a9600ae744b57aac01d486ba357ec
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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