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 1453196Notes

Reaction equation

HRID 1453196 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%. 1H NMR (300 MHz, DMSO-d6) δ 1.10 (t, J=7.8 Hz, 3H), 1.25-1.73 (m, 8H), 1.89 (m, 2H), 2.33 (m, 1H), 2.43-2.53 (m, 2H, overlap with DMSO-d5), 2.58 (q, m, overlap, 3H), 2.76 (d, J=18 Hz, 1H), 3.75 (ABQ pattern, J=16 Hz, 2H), 3.77 (s, 3H), 3.84 (s, 3H), 6.71 (s, 1H), 7.10 (s, 1H), 11.31 (br s, 1H). LC-MS (APCI) calcd for C25H31ClN2O6: 490.19; found (M+H+) 491.0 m/z.

Sources & evidence

ORD record
ord-557fe0a3aada484d8e2f84638eef621d
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

Loading…