3-Chloro-6-ethyl-4-hydroxy-6-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one → 3-(5-Chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-ethyl-4-hydroxy-6-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 1453255Notes

Reaction equation

HRID 1453255 reaction equation
Cl[C:2]1[C:3](=[O:21])[O:4][C:5]([CH2:19][CH3:20])([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:6][C:7]=1[OH:8].[Cl:22][C:23]1[CH:35]=[CH:34][C:26]2[N:27]([CH:31]([CH3:33])[CH3:32])[C:28]([SH:30])=[N:29][C:25]=2[CH:24]=1>>[Cl:22][C:23]1[CH:35]=[CH:34][C:26]2[N:27]([CH:31]([CH3:33])[CH3:32])[C:28]([S:30][C:2]3[C:3](=[O:21])[O:4][C:5]([CH2:19][CH3:20])([CH2:9][CH2:10][C:11]4[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=4)[CH2:6][C:7]=3[OH:8])=[N:29][C:25]=2[CH:24]=1

Participants

3

Reactant 2

HCID 587626223-Chloro-6-ethyl-4-hydroxy-6-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-oneHCID 178456613HCID 178456613, compound

Product 1

HCID 587624063-(5-Chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-ethyl-4-hydroxy-6-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared from 3-Chloro-6-ethyl-4-hydroxy-6-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one from Step 1 and 5-Chloro-1-isopropyl-1H-benzoimidazole-2-thiol using the coupling method described in Example C(4), 1H NMR (CDCl3): δ 0.96 (t, 3H, J=7.5 Hz), 1.69 (d, 6H, J=7.0 Hz), 1.85 (m, 2H), 1.98 (m, 2H), 2.59 (m, 2H), 2.71 (s, 2H), 3.78 (s, 3H), 5.16 (m, 1H), 6.81 (d, 2H, J=8.5 Hz), 7.06 (d, 2H, J=8.5 Hz), 7.28 (d, 2H, J=8.9 Hz), 7.48 (d, 1H, J=8.9 Hz), 7.59 (s, 1H). ESIMS: MH+ 501.10, 503.10, MH− 4.99.10, 501.10.

Sources & evidence

ORD record
ord-0150b4c923374363b86a24fbeb81ed65
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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