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

HRID 1453261Notes

Reaction equation

HRID 1453261 reaction equation
Cl[C:2]1[C:3](=[O:27])[O:4][C:5]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([Cl:26])[CH:17]=2)([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:6][C:7]=1[OH:8].ClC1C(=O)OC(CCC2CCCCC=2)(C2CCCC2)CC=1O.[Cl:50][C:51]1[CH:63]=[CH:62][C:54]2[N:55]([CH:59]([CH3:61])[CH3:60])[C:56]([SH:58])=[N:57][C:53]=2[CH:52]=1.N1C=CC(C2NC(S)=NN=2)=CC=1>>[Cl:26][C:18]1[CH:17]=[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:58][C:56]3[N:55]([CH:59]([CH3:61])[CH3:60])[C:54]4[CH:62]=[CH:63][C:51]([Cl:50])=[CH:52][C:53]=4[N:57]=3)=[C:7]([OH:8])[CH2:6]2)[CH:21]=[CH:20][C:19]=1[O:22][CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 547203163-Chloro-6-[2-(3-chloro-4-isopropoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-oneHCID 575272693-Chloro-6-(2-cyclohex-1-enyl-ethyl)6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-oneHCID 178456613HCID 178456613, compoundHCID 1785279605-pyridin-4-yl-1H-1,2,4-triazole-3-thiol

Product 1

HCID 587624736-[2-(3-Chloro-4-isopropoxy-phenyl)-ethyl]-3-(5-chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared analogously to Example C(4), where 3-Chloro-6-[2-(3-chloro-4-isopropoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one (from Step 1 below) was substituted in place of 3-Chloro-6-(2-cyclohex-1-enyl-ethyl)-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one and 5-Chloro-1-isopropyl-2-mercapto benzimidazole was substituted in place of 5-Pyridin-4-yl-4H-[1,2,4]triazole-3-thiol of that example. 1H NMR (DMSO-d6): δ 1.13 (d, J=6.1 Hz, 6H), 1.41 (d, J=7.1 Hz, 6H), 1.42-1.8 (m, 10H), 2.08-2.13 (m, 1H), 2.43-2.54 (m 3H), 2.79 (d, J=17.0, 1H), 4.44-4.48 (m, 1H), 4.63-4.69 (m, 1H), 6.89-6.91 (m, 2H), 6.95-7.00 (m, 2H), 7.14 (s, 1H), 7.49 (d, J=8.6 Hz, 1H), 12.0 (brs, 1H); Anal. Calcd. For C31H36Cl2N2O4S.1.0AcOH: C, 59.72; H, 6.07; N, 4.22; Found: C, 59.50; H, 6.16; N, 4.33. ESIMS (MH+): 604.

Sources & evidence

ORD record
ord-91f4fc0b0f66448c8651d2efe82867f8
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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