5-chloro-2-[2-(5-chloro-2,4-dimethoxy-phenyl)ethyl]-2-cyclopentyl-4-hydroxy-3H-pyran-6-one → 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-3-[(5-chloro-1-methyl-1H-benzimidazol-2-yl)thio]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one

HRID 1453274Notes

Reaction equation

HRID 1453274 reaction equation
Cl[C:2]1[C:3](=[O:27])[O:4][C:5]([CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[C:19]([O:23][CH3:24])=[CH:18][C:17]=2[O:25][CH3:26])([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:6][C:7]=1[OH:8].ClC1C(=O)OC(CCC2C=CC(OC)=C(Cl)C=2)(C2CCCC2)CC=1O.[Cl:53][C:54]1[CH:64]=[CH:63][C:57]2[N:58]([CH3:62])[C:59]([SH:61])=[N:60][C:56]=2[CH:55]=1.ClC1C=CC2N(C(C)C)C(S)=NC=2C=1>>[Cl:22][C:20]1[C:19]([O:23][CH3:24])=[CH:18][C:17]([O:25][CH3:26])=[C:16]([CH2:15][CH2:14][C:5]2([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[O:4][C:3](=[O:27])[C:2]([S:61][C:59]3[N:58]([CH3:62])[C:57]4[CH:63]=[CH:64][C:54]([Cl:53])=[CH:55][C:56]=4[N:60]=3)=[C:7]([OH:8])[CH2:6]2)[CH:21]=1

Participants

5

Reactant 4

HCID 546895495-chloro-2-[2-(5-chloro-2,4-dimethoxy-phenyl)ethyl]-2-cyclopentyl-4-hydroxy-3H-pyran-6-oneHCID 547203223-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-oneHCID 178456613HCID 178456613, compoundHCID 1784816675-chloro-1-methyl-1H-benzo[d]imidazole-2-thiol

Product 1

HCID 587626916-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-3-[(5-chloro-1-methyl-1H-benzimidazol-2-yl)thio]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one

Procedure

The title compound was prepared analogously to Example C(40), where 3-chloro-6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one was substituted in place of 3-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one and 5-chloro-1-methyl-1H-benzimidazole-2-thiol was substituted in place of 5-chloro-1-isopropyl-1H-benzimidazole-2-thiol. 1H NMR (300 MHz, DMSO-D6) δ: 1.37-1.71 (m, 8H), 2.07-2.19 (m, 2H), 2.35-2.42 (m, 1H), 2.57-2.72 (m, 3H), 2.83-2.88 (m, 1H), 3.71 (s, 3H), 3.75 (s, 3H), 3.86 (s, 3H), 6.71 (s, 1H), 7.01 (d, J=1.70 Hz, 1H), 7.13 (s, 1H), 7.16 (d, J=2.07 Hz, 1H), 7.45 (d, J=8.67 Hz, 1H). ESI-MS calcd for C28H30Cl2N2O5S: 576.1. Found (M+H+): 577.1. Anal. Calcd. For C28H30Cl2N2O5S.1.0H2O: C, 56.47; H, 5.42; N, 4.70; S, 5.38. Found: C, 56.86; H, 5.24; N, 5.05; S, 5.20.

Sources & evidence

ORD record
ord-6ab0ed6de506426286dc41a5ef33bd8a
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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