6-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione → HCID 136152594, compound

HRID 1453199Notes

Reaction equation

HRID 1453199 reaction equation
Br[CH2:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[Cl:14][C:15]1[C:16]([O:38][CH3:39])=[CH:17][C:18]([O:36][CH3:37])=[C:19]([CH2:21][CH2:22][C:23]2([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:28][C:27](=[O:29])[CH2:26][C:25](=[O:30])[CH2:24]2)[CH:20]=1>>[Cl:14][C:15]1[C:16]([O:38][CH3:39])=[CH:17][C:18]([O:36][CH3:37])=[C:19]([CH2:21][CH2:22][C:23]2([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:28][C:27](=[O:29])[C:26]([CH2:2][C:3]3[NH:12][C:11](=[O:13])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]=3)=[C:25]([OH:30])[CH2:24]2)[CH:20]=1

Participants

3

Reactant 2

HCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dioneHCID 1354540342-(bromomethyl)quinazolin-4(1h)-one

Product 1

HCID 136152594HCID 136152594, compoundYield 19%

Procedure

The title compound was prepared as described in Example B(53), using 2-(bromomethyl)-quinazolin-4(3H)-one (Example B(55), 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: 19%. 1H NMR (300 MHz, DMSO-d6) δ 1.33-1.74 (m, 8H), 1.99 (m, 1H), 2.23 (m, 1H), 2.37 (m, 1H), 2.45-2.53 (m, 2H, overlap with DMSO-d5), 2.58 (d, J=17.5 Hz, 1H), 2.78 (d, J=17.5 Hz, 1H), 3.59 (ABQ pattern, J=16.6 Hz, 2H), 3.73 (s, 3H), 3.84 (s, 3H), 6.69 (s, 1H), 7.01 (d, J=8 Hz, 1H), 7.13 (s, 1H), 7.42 (t, J=8 Hz, 1H), 7.57 (t, J=8 Hz, 1H), 8.03 (d, J=8 Hz, 1H). LC-MS (APCI) calcd for C29H31ClN2O6: 538.19; found (M+H+) 539.0 m/z.

Sources & evidence

ORD record
ord-c13a7963874041c6a3a75425f1cd292f
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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