5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 2-[4-(2-{2-Cyclopentyl-5-[(1,3-dimethyl-1H-1,2,4-triazol-5-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-fluorophenyl]-2-methylpropanenitrile

HRID 859665Notes

Reaction equation

HRID 859665 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[C:18]([F:27])[CH:17]=3)[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(CCC2(C3CCCC3)OC(=O)CC(=O)C2)C=C(CC)C=1OC.[CH3:54][N:55]1[C:59]([CH:60]=O)=[N:58][C:57]([CH3:62])=[N:56]1.CC1C=C(C)N2N=C(C=O)N=C2N=1>O>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:26])[C:23]#[N:24])=[C:18]([F:27])[CH:17]=3)[CH2:11][C:10]([OH:12])=[C:9]([CH2:60][C:59]3[N:55]([CH3:54])[N:56]=[C:57]([CH3:62])[N:58]=3)[C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

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 587624232-{4-[2-(2-cyclopentyl-4,6-dioxotetrahydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl)-2-methylpropanenitrileHCID 834786731,3-dimethyl-1H-1,2,4-triazole-5-carbaldehyde

Product 1

HCID 587642232-[4-(2-{2-Cyclopentyl-5-[(1,3-dimethyl-1H-1,2,4-triazol-5-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-fluorophenyl]-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared analogously to example A(1), where 2-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl-2-methyl-propionitrile.from step 3 below, was substituted in place of 6-[2-(3-Chloro-5-ethyl-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione and 2,5-Dimethyl-2H-[1,2,4]triazole-3-carbaldehyde was substituted instead of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde in that example. 1H NMR (300 MHz, DMSO-d6): δ 1.49–1.69 (m, 8 H), 1.72 (s, 6 H), 2.06 (s, 3 H), 2.11 (s, 3 H), 2.12–2.13 (m, 2 H), 2.34–2.42 (m, 1H), 2.55–2.66 (m, 3H), 2.80 (d, J=17 Hz, 1 H), 3.42–3.65 (m, 2 H), 7.08–7.18 (m, 2 H), 7.35–7.40 (m, 1 H). Anal. Calcd. For C27H33FN4O3.0.25 H2O: C, 66.85; H, 6.96; N, 11.55; Found: C, 66.88; H, 6.99; N, 11.60. ESIMS (MH+): 481.

Sources & evidence

ORD record
ord-9434010f5099412e99689677733827bb
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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