3-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione → 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-[(4,5-dimethyl-4H-1,2,4-triazol-3-yl)thio]-4-hydroxy-5,6-dihydro-2H-pyran-2-one
Reaction equation
Cl[CH:2]1[C:7](=[O:8])[CH2:6][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)[O:4][C:3]1=[O:25].[CH3:26][N:27]1[C:31]([CH3:32])=[N:30][N:29]=[C:28]1[SH:33].O.OC1N=CN=C2C=1NC(S)=N2>O>[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])[C:2]([S:33][C:28]3[N:27]([CH3:26])[C:31]([CH3:32])=[N:30][N:29]=3)=[C:7]([OH:8])[CH2:6]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared as described in Example C(70), where 3-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione was used in place of 3-chloro-6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione and 4,5-dimethyl-4H-1,2,4-triazole-3-thiol, as shown in Example C(88), Step 1, was used in place of 6-hydroxy-8-mercaptopurine monohydrate. 1H NMR (500 MHz, DMSO-d6, WET suppression of DMSO-h6 (2.5 ppm) and H2O (3.35 ppm) peak areas) δ 1.49-1.64 (m, 8H) 1.92 (m, 2H) 2.33 (m, 1H) 2.37 (s, 3H) 2.50 (m, 2H, overlap with dmso) 2.62 (d, J=15 Hz, 1H) 2.80 (d, J=17.6 Hz, 1H) 3.55 (s, attenuation due to proximity to H2O peak) 3.80 (s, 3H) 7.02 (d, J=8.5 Hz, 1H) 7.12 (dd, J=8.5, 1.9 Hz, 1H) 7.24 (d, J=1.9 Hz, 1H). MS (APCI) calcd for C23H28ClN3O4S: 478.01; found M=478.1.
Sources & evidence
- ORD record
- ord-d177e7b35de846abb6a36a78011c51c2
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473790B2
Reaction notes
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