3-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione → HCID 178489974, compound

HRID 1453287Notes

Reaction equation

HRID 1453287 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].[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[NH:33][C:34]([SH:37])=[N:35][N:36]=2)[CH:27]=1>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:37][C:34]3[NH:33][C:32]([C:28]4[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=4)=[N:36][N:35]=3)=[C:7]([OH:8])[CH2:6]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 688674513-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dioneHCID 178527950HCID 178527950, compound

Product 1

HCID 178489974HCID 178489974, compound

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 5-(3-pyridinyl)-4H-1,2,4-triazole-3-thiol 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 1.53-1.69 (m, 8H) 2.03 (m, 1H) 2.11 (m, 1H) 2.35 (m, 1H) 2.57 (m, 1H) 2.63 (m, 1H) 2.82 (d, J=17.6 Hz, 1H) 2.96 (d, J=15.0 Hz, 1H) 3.77 (s, 3H) 6.95 (d, J=8.5 Hz, 1H) 7.09 (d, J=8.5 Hz, 1H) 7.23 (d, J=1.4 Hz, 1H) 7.41 (m, 1H) 8.13 (s, 1H) 8.60 (d, J=4.1 Hz, 1H) 9.03 (s, 1H). MS (APCI) calcd for C26H27ClN4O4S: 527.04; found M=527.0.

Sources & evidence

ORD record
ord-0e6459472d7f4ab09b84a23a78fa09ab
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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