6-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione → HCID 136152588, compound

HRID 1453197Notes

Reaction equation

HRID 1453197 reaction equation
Cl[CH2:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][C:7]([O:16][CH3:17])=[C:8]([O:14][CH3:15])[CH:9]=2)[N:4]=1.[Cl:18][C:19]1[C:20]([O:42][CH3:43])=[CH:21][C:22]([O:40][CH3:41])=[C:23]([CH2:25][CH2:26][C:27]2([CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[O:32][C:31](=[O:33])[CH2:30][C:29](=[O:34])[CH2:28]2)[CH:24]=1>>[Cl:18][C:19]1[C:20]([O:42][CH3:43])=[CH:21][C:22]([O:40][CH3:41])=[C:23]([CH2:25][CH2:26][C:27]2([CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[O:32][C:31](=[O:33])[C:30]([CH2:2][C:3]3[NH:12][C:11](=[O:13])[C:10]4[C:5](=[CH:6][C:7]([O:16][CH3:17])=[C:8]([O:14][CH3:15])[CH:9]=4)[N:4]=3)=[C:29]([OH:34])[CH2:28]2)[CH:24]=1

Participants

3

Reactant 2

HCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dioneHCID 1354735692-(chloromethyl)-6,7-dimethoxyquinazolin-4(3H)-one

Product 1

HCID 136152588HCID 136152588, compoundYield 20%

Procedure

The title compound was prepared as described in Example B(53), using 2-(chloromethyl)-6,7-dimethoxyquinazolin-4(3H)-one (Example B(57), Step 1) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 20%. 1H NMR (300 MHz, DMSO-d6) δ 1.27-1.75 (m, 8H), 1.85 (m, 1H), 2.05 (m, 1H), 2.37 (m, 1H), 2.50 (m, 2H, overlap with DMSO-d5), 2.53 (d, J=18 Hz, 1H), 2.69 (d, J=18 Hz, 1H), 3.59 (m, 2H, overlap with H2O), 3.62 (s, 3H, overlap with H2O), 3.67 (s, 3H, overlap with H2O), 3.81 (s, 3H, overlap with H2O), 3.84 (s, 3H, overlap with H2O), 6.61 (s, 1H), 6.63 (s, 1H), 7.13 (s, 1H), 7.39 (s, 1H). LC-MS (APCI) calcd for C31H35ClN2O8: 598.21; found (M+H+) 599.1 m/z.

Sources & evidence

ORD record
ord-d73a66c8b2af4e0e9f77b3ba50e67101
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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