5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 2-[2-Chloro-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)phenyl]-2-methylpropanenitrile

HRID 1438301Notes

Reaction equation

HRID 1438301 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[O:11]2)[CH:5]=[CH:4][C:3]=1[C:23]([CH3:27])([CH3:26])[C:24]#[N:25].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>>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:15][C:14]([OH:16])=[C:13]([CH2:60][C:59]3[N:55]([CH3:54])[N:56]=[C:57]([CH3:62])[N:58]=3)[C:12](=[O:17])[O:11]2)[CH:5]=[CH:4][C:3]=1[C:23]([CH3:27])([CH3:26])[C:24]#[N:25]

Participants

5

Reactant 4

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 498714082-{2-Chloro-4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-phenyl}-2-methyl-propionitrileHCID 587622136-[2-(3-Chloro-5-ethyl-4-methoxy-phenyl)-ethyl]6-cyclopentyl-dihydro-pyran-2,4-dioneHCID 834786731,3-dimethyl-1H-1,2,4-triazole-5-carbaldehyde

Product 1

HCID 587641942-[2-Chloro-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)phenyl]-2-methylpropanenitrile

Procedure

The title compound was prepared analogously to example A(1): where 2-{2-chloro-4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-phenyl}-2-methyl-propionitrile from step 5 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 1.47-1.74 (m, 8H), 1.79 (s, 6H), 2.01-2.11 (m, 8H), 2.36-2.42 (m, 1H), 2.56 (d, J=16 Hz, 1H), 2.60-2.66 (m, 2H), 2.77 (d, J=16 Hz, 1H), 3.53 (d, J=16 Hz, 1H), 3.62 (d, J=16 Hz, 1H), 7.25 (dd, J=8.2, 1.8 Hz, 1H), 7.4 (d, J=1.8 Hz, 1H), 7.45 (d, J=8.2 Hz, 1H). Anal. Calcd. For C27H33ClN4O3.0.25H2O: C, 64.66; H, 6.73; N, 11.17. Found: C, 64.88; H, 6.74; N, 10.86. ESIMS (MH+): 498.

Sources & evidence

ORD record
ord-a451c513c1184d749ef7e145034737d2
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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