3-Chloro-6-(2-cyclohex-1-enyl-ethyl)6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one → 3-(5-Chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-cyclopentyl-6-(2-cyclopentyl-ethyl)-4-hydroxy-5,6-dihydro-pyran-2-one

HRID 1453266Notes

Reaction equation

HRID 1453266 reaction equation
Cl[C:2]1[C:3](=[O:21])[O:4][C:5]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)([CH2:9][CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:6][C:7]=1[OH:8].ClC1C(=O)OC(CCC2CCCCC=2)(C2CCCC2)CC=1O.[Cl:44][C:45]1[CH:57]=[CH:56][C:48]2[N:49]([CH:53]([CH3:55])[CH3:54])[C:50]([SH:52])=[N:51][C:47]=2[CH:46]=1.N1C=CC(C2NC(S)=NN=2)=CC=1>>[Cl:44][C:45]1[CH:57]=[CH:56][C:48]2[N:49]([CH:53]([CH3:55])[CH3:54])[C:50]([S:52][C:2]3[C:3](=[O:21])[O:4][C:5]([CH:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)([CH2:9][CH2:10][CH:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)[CH2:6][C:7]=3[OH:8])=[N:51][C:47]=2[CH:46]=1

Participants

5

Reactant 4

HCID 575272693-Chloro-6-(2-cyclohex-1-enyl-ethyl)6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-oneHCID 688672163-Chloro-6-cyclopentyl-6-(2-cyclopentyl-ethyl)-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 587622093-(5-Chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-cyclopentyl-6-(2-cyclopentyl-ethyl)-4-hydroxy-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared analogously to Example C(4), where 3-Chloro-6-cyclopentyl-6-(2-cyclopentyl-ethyl)-4-hydroxy-5,6-dihydro-pyran-2-one from Step 2 of example C(28) 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 0.84-2.28 (m, 28H), 2.31 (d, J=17.0, 1H), 2.66 (d, J=17.0, 1H), 3.96 (brs, 1H), 4.55-4.67 (m, 1H), 6.93 (d, J=8.5, 1H), 7.12 (s, 1H), 7.46 (d, J=8.5, 1H); Anal. Calcd. For C27H35ClN2O3S: C, 64.46; H, 7.01; N, 5.57; Found: C, 64.85; H, 7.30; N, 5.76. ESIMS (MH+): 504.

Sources & evidence

ORD record
ord-d998074c460d4023b8f32ebe9182b00d
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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