3-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione → Methyl 5-({6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}thio)-4-methyl-4H-1,2,4-triazole-3-carboxylate

HRID 1453293Notes

Reaction equation

HRID 1453293 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].[SH:26][C:27]1[N:28]([CH3:36])[C:29]([C:32]([O:34][CH3:35])=[O:33])=[N:30][N:31]=1.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:26][C:27]3[N:28]([CH3:36])[C:29]([C:32]([O:34][CH3:35])=[O:33])=[N:30][N:31]=3)=[C:7]([OH:8])[CH2:6]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 688674513-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dioneHCID 178499171HCID 178499171, compoundHCID 178526943HCID 178526943, compound

Product 1

HCID 58762234Methyl 5-({6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}thio)-4-methyl-4H-1,2,4-triazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 methyl 5-mercapto-4-methyl-4H-1,2,4-triazole-3-carboxylate, as shown in Example 21, Step 2, 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 1.50-1.70 (s, 8H) 1.98 (m, 2H) 2.35 (m, 1H) 2.50 (m, 1H, overlap with dmso) 2.63 (m, 1H) 2.71 (d, J=18.1 Hz, 1H) 2.90 (d, J=17.6 Hz, 1H) 3.81 (s, 3H) 3.81 (s, 3H) 3.88 (s, 3H) 7.02 (d, J=8.2 Hz, 1H) 7.15 (dd, J=8.2, 1.9 Hz, 1H) 7.27 (d, J=1.9 Hz, 1H). MS (APCI) calcd for C24H28ClN3O6S: 522.02; found M=522.1.

Sources & evidence

ORD record
ord-259e9c71d0d746fea3077d6124656e7b
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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