5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 6-Cyclopentyl-6-{2-[3-ethyl-4-(1,3-oxazol-2-yl)phenyl]ethyl}-4-hydroxy-3-([1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-5,6-dihydro-2H-pyran-2-one

HRID 859693Notes

Reaction equation

HRID 859693 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][CH:24]=[CH:25][N:26]=4)=[C:18]([CH2:27][CH3:28])[CH:17]=3)[O:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C2(CCC3C=C(CC)C(O)=CC=3OCCC)OC(=O)CC(=O)C2)CCCC1.CO[CH:59]([C:61]1[N:69]=[C:64]2[N:65]=[CH:66][CH:67]=[CH:68][N:63]2[N:62]=1)O.CC1C=C(C)N2N=C(C=O)N=C2N=1>>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][CH:24]=[CH:25][N:26]=4)=[C:18]([CH2:27][CH3:28])[CH:17]=3)[O:11][C:10](=[O:12])[C:9]([CH2:59][C:61]3[N:69]=[C:64]4[N:65]=[CH:66][CH:67]=[CH:68][N:63]4[N:62]=3)=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587640596-cyclopentyl-6-{2-[3-ethyl-4-(1,3-oxazol-2-yl)phenyl]ethyl}dihydro-2H-pyran-2,4(3H)-dioneHCID 587641376-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dioneHCID 69063119Methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl-methanol

Product 1

HCID 587641426-Cyclopentyl-6-{2-[3-ethyl-4-(1,3-oxazol-2-yl)phenyl]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(1) where 6-cyclopentyl-6-{2-[3-ethyl-4-(1,3-oxazol-2-yl)phenyl]ethyl}dihydro-2H-pyran-2,4(3H)-dione (Example A(135)) was substituted in place of 6-cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione in that example and methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl-methanol was substituted in place of 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde. Yield (57 mg, 11%). 1H NMR (300 MHz, CDCl3): δ ppm 1.20 (t, J=7.44 Hz, 3 H) 1.53–1.67 (m, 8 H) 2.00–2.11 (m, 2 H) 2.35–2.47 (m, 1 H) 2.51–2.63 (m, 1 H) 2.65–2.72 (m, 2 H) 2.72–2.83 (m, 2 H) 3.04 (q, J=7.54 Hz, 2 H) 4.14 (d, J=3.77 Hz, 2 H) 7.04–7.10 (m, 2 H) 7.14–7.20 (m, 1 H) 7.25 (s, 1 H) 7.71 (s, 1 H) 7.82 (d, J=7.91 Hz, 1 H) 8.84 (d, J=5.46 Hz, 2 H). MS (ESI): 514 (M+H)+.

Workup

  1. customYield (57 mg, 11%)

Sources & evidence

ORD record
ord-84f6b42b840047f69b04ab67696d2b03
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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