6-cyclopentyl-6-[2-(3,5-diethyl-4-hydroxyphenyl)ethyl]dihydro-2H-pyran-2,4(3H)-dione → 6-cyclopentyl-6-[2-(3,5-diethyl-4-hydroxyphenyl)ethyl]-4-hydroxy-3-([1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-5,6-dihydro-2H-pyran-2-one

HRID 858689Notes

Reaction equation

HRID 858689 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]2=[N:3][C:2]=1[CH:10]=O.[CH:12]1([C:17]2([CH2:25][CH2:26][C:27]3[CH:32]=[C:31]([CH2:33][CH3:34])[C:30]([OH:35])=[C:29]([CH2:36][CH3:37])[CH:28]=3)[O:22][C:21](=[O:23])[CH2:20][C:19](=[O:24])[CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:12]1([C:17]2([CH2:25][CH2:26][C:27]3[CH:32]=[C:31]([CH2:33][CH3:34])[C:30]([OH:35])=[C:29]([CH2:36][CH3:37])[CH:28]=3)[O:22][C:21](=[O:23])[C:20]([CH2:10][C:2]3[N:3]=[C:4]4[N:9]=[CH:8][CH:7]=[CH:6][N:5]4[N:1]=3)=[C:19]([OH:24])[CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 587625206-cyclopentyl-6-[2-(3,5-diethyl-4-hydroxyphenyl)ethyl]dihydro-2H-pyran-2,4(3H)-dioneHCID 58764260[1,2,4]Triazolo[1,5-a]pyrimidine-2-carbaldehyde

Product 1

HCID 587623806-cyclopentyl-6-[2-(3,5-diethyl-4-hydroxyphenyl)ethyl]-4-hydroxy-3-([1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-5,6-dihydro-2H-pyran-2-one

Procedure

The title compound was prepared analogously to Example A(224) where [1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde was used in place of 6-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde and 6-cyclopentyl-6-[2-(3,5-diethyl-4-hydroxyphenyl)ethyl]dihydro-2H-pyran-2,4(3H)-dione (Example A(235)) was used in place of 6-cyclopentyl-6-{2-[4-hydroxy-3-(2,2,2-trifluoroethyl)phenyl]ethyl}dihydro-2H-pyran-2,4(3H)-dione in that example. 1H NMR (DMSO): δ 1.20 (t, J=2.56 Hz, 6H), 1.30–1.80 (brm, 6H), 2.00–2.18 (brm, 5H), 2.40 (q, J=20.06 Hz 4H), 2.80 (m, 4H), 3.45 (m, 3H), 6.70 (s, 2H), 7.17 (d, J=2.54 Hz, 1H), 8.80 (m, 2H), 9.29 (s, 1H). Anal. Calcd. For C28H34O4N4, C, 68.55; H, 6.99, N, 11.42. Found: C, 68.80; H, 7.31; N, 11.45.

Sources & evidence

ORD record
ord-86da99a91026456cb3a68404286f945e
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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