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

HRID 858755Notes

Reaction equation

HRID 858755 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:4]=1.[Cl:14][C:15]1[C:16]([O:38][CH3:39])=[CH:17][C:18]([O:36][CH3:37])=[C:19]([CH2:21][CH2:22][C:23]2([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:28][C:27](=[O:29])[CH2:26][C:25](=[O:30])[CH2:24]2)[CH:20]=1>>[Cl:14][C:15]1[C:16]([O:38][CH3:39])=[CH:17][C:18]([O:36][CH3:37])=[C:19]([CH2:21][CH2:22][C:23]2([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:28][C:27](=[O:29])[C:26]([CH2:2][C:3]3[O:7][N:6]=[C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=4)[N:4]=3)=[C:25]([OH:30])[CH2:24]2)[CH:20]=1

Participants

3

Reactant 2

HCID 151337662-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)pyridineHCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione

Product 1

HCID 587622166-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-3-[(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)methyl]-5,6-dihydro-2H-pyran-2-oneYield 9%

Procedure

The title compound was prepared as described in Example B(53), using 2-[5-(chloromethyl)-1,2,4-oxadiazol-3-yl]pyridine (from 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]-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 9%.

Sources & evidence

ORD record
ord-e3c80d7e63ec4bf1bb483aac5207e1d0
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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