6-[2-(4-Benzyloxyphenyl)ethyl]-6-cyclopentyldihydropyran-2,4-dione → HCID 136152591, compound

HRID 1453201Notes

Reaction equation

HRID 1453201 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([CH:9]2[CH2:11][CH2:10]2)[NH:6][C:5](=[O:12])[CH:4]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]2([CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[O:34][C:33](=[O:35])[CH2:32][C:31](=[O:36])[CH2:30]2)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]2([CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[O:34][C:33](=[O:35])[C:32]([CH2:2][C:3]3[N:8]=[C:7]([CH:9]4[CH2:11][CH2:10]4)[NH:6][C:5](=[O:12])[CH:4]=3)=[C:31]([OH:36])[CH2:30]2)=[CH:23][CH:22]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 219385336-[2-(4-Benzyloxyphenyl)ethyl]-6-cyclopentyldihydropyran-2,4-dioneHCID 1355243894(1H)-Pyrimidinone,6-(chloromethyl)-2-cyclopropyl-(9CI)

Product 1

HCID 136152591HCID 136152591, compoundYield 12%

Procedure

The title compound was prepared as described in Example B(53), using 6-(chloromethyl)-2-cyclopropylpyrimidin-4(3H)-one in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-{2-[4-(benzyloxy)phenyl]ethyl}-6-cyclopentyldihydro-2H-pyran-2,4-(3H)-dione (Step 6, below) in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 12%. 1H NMR (300 MHz, DMSO-d6) δ 0.91 (m, 4H), 1.15-1.65 (m, 8H), 1.82-1.92 (m, 3H), 2.34 (m, 1H), 2.38-2.58 (m, 3H, overlap with DMSO-d5), 2.75 (d, J=18 Hz, 1H), 3.29 (ABQ pattern, J=16.7 Hz, 2H), 5.05 (s, 2H), 5.72 (s, 1H), 6.90 (d, J=8.4 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 7.43-7.28 (m, 5H). LC-MS (APCI) calcd for C33H36N2O5: 540.26; found (M+H+) 541.1 m/z.

Sources & evidence

ORD record
ord-5982ba7816bd4fde827ffeccbe54be85
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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