Hydrochloric Acid → 6-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-3-(5-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-dihydro-pyran-2,4-dione

HRID 1453259Notes

Reaction equation

HRID 1453259 reaction equation
Cl[C:2]1[C:3](=[O:25])[O:4][C:5]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[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.[C:48]1([C:54]2[NH:58][N:57]=[C:56]([SH:59])[N:55]=2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.N1C=CC(C2NC(S)=NN=2)=CC=1.Cl>>[Cl:24][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:25])[CH:2]([S:59][C:56]3[NH:55][C:54]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[N:58][N:57]=3)[C:7](=[O:8])[CH2:6]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 547203223-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-oneHCID 575272693-Chloro-6-(2-cyclohex-1-enyl-ethyl)6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-oneHCID 1785279605-pyridin-4-yl-1H-1,2,4-triazole-3-thiolHCID 178527978HCID 178527978, compound

Product 1

HCID 1784899736-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-3-(5-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-dihydro-pyran-2,4-dione

Procedure

The title compound was prepared analogously to Example C(4), where 3-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one Step 1 of example C(40), 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-Phenyl-1H-1,2,4-triazole-3-thiol was substituted in place of 5-Pyridin-4-yl-4H-[1,2,4]triazole-3-thiol of that example. 1H NMR (DMSO-d6): δ 1.53-1.85 (m, 10H), 2.17-2.34 (m, 1H), 2.69-2.75 (m 2H), 2.95 (d, J=17.0, 1H), 3.08 (d, J=17.0 Hz, 1H), 3.90 (s, 3H), 7.08 (d, J=8.4 Hz, 1H) 7.22-7.26 (m, 1H), 7.40 (d, J=2.0 Hz, 1H), 7.40-7.53 (m, 4H), 7.91-7.94 (m, 2H), 12.0 (brs, 1H); Anal. Calcd. For C27H28ClN3O4S.1.0 HCl.1.0H2O: C, 55.86; H, 5.38; N, 7.24; Found: C, 55.75; H, 5.17; N, 7.17. ESIMS (MH+): 527

Sources & evidence

ORD record
ord-274b851f347c4c2ba41990392771bc62
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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