5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 3-(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-cyclopentyl-6-[2-(2,4-dimethoxy-phenyl)-ethyl]-4-hydroxy-5,6-dihydro-pyran-2-one

HRID 858791Notes

Reaction equation

HRID 858791 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH:11]=O)[N:10]=2)[CH:7]=1.CC1C=C(C)N2N=C(C=O)N=C2N=1.[CH:26]1([C:31]2([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][C:42]=3[O:49][CH3:50])[O:36][C:35](=[O:37])[CH:34]=[C:33]([OH:38])[CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27]1.ClC1C=C(CCC2(C3CCCC3)OC(=O)CC(=O)C2)C=C(CC)C=1OC>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH2:11][C:34]3[C:35](=[O:37])[O:36][C:31]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)([CH2:39][CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][C:42]=4[O:49][CH3:50])[CH2:32][C:33]=3[OH:38])[N:10]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587622136-[2-(3-Chloro-5-ethyl-4-methoxy-phenyl)-ethyl]6-cyclopentyl-dihydro-pyran-2,4-dioneHCID 587625546-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 688676766-Cyclopentyl-6-[2-(2,4-dimethoxy-phenyl)-ethyl]4-hydroxy-5,6-dihydro-pyran-2-one

Product 1

HCID 587626233-(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-cyclopentyl-6-[2-(2,4-dimethoxy-phenyl)-ethyl]-4-hydroxy-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared analogously to Example B(97), where 6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde was substituted in place of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde and 6-Cyclopentyl-6-[2-(2,4-dimethoxy-phenyl)-ethyl]4-hydroxy-5,6-dihydro-pyran-2-one was substituted in place of 6-[2-(3-Chloro-5-ethyl-4-methoxy-phenyl)-ethyl]6-cyclopentyl-dihydro-pyran-2,4-dione of that example. 1H NMR (400 MHz, DMSO-d6): δ 1.51–1.73 (m, 9H), 1.92–1.98 (m, 2H), 2.38–2.58 (m, 3H), 2.79 (d, J=16 Hz, 1H), 3.71 (s, 2H), 3.73 (s, 6H), 6.40–6.5 (m, 2H), 7.03 (d, J=8 Hz, 1H), 8.89 (d, J=2.6 Hz, 1H), 9.52 (d, J=2.6 Hz, 1H), 10.9 (s, 1H). Anal. Calcd. For C26H29ClN4O5.0.25H2O: C, 60.35; H, 5.75; N, 10.83. Found: C, 60.40; H, 5.65; N, 10.74. MS (ESI): 513 (M+H)+.

Sources & evidence

ORD record
ord-cd02604217a645528640e812032138e6
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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