1-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopentanecarbonitrile → 1-(4-{2-[5-(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-2-fluoro-phenyl)-cyclopentanecarbonitrile

HRID 1453117Notes

Reaction equation

HRID 1453117 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.C(C1NC(C=O)=C(C)N=1)C.[CH:23]1([C:28]2([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([C:44]4([C:49]#[N:50])[CH2:48][CH2:47][CH2:46][CH2:45]4)=[C:40]([F:51])[CH:39]=3)[CH2:33][C:32](=[O:34])[CH2:31][C:30](=[O:35])[O:29]2)[CH2:27][CH2:26][CH2:25][CH2:24]1.C1(C2(CCC3C=CC(C(C)(C)C#N)=C(F)C=3)CC(O)=CC(=O)O2)CCCC1>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH2:11][C:31]3[C:30](=[O:35])[O:29][C:28]([CH2:36][CH2:37][C:38]4[CH:43]=[CH:42][C:41]([C:44]5([C:49]#[N:50])[CH2:45][CH2:46][CH2:47][CH2:48]5)=[C:40]([F:51])[CH:39]=4)([CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[CH2:33][C:32]=3[OH:34])[N:10]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 587623021-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopentanecarbonitrileHCID 587625546-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 688686862-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl]-2-methylpropanenitrileHCID 178437630HCID 178437630, compound

Product 1

HCID 587625371-(4-{2-[5-(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-2-fluoro-phenyl)-cyclopentanecarbonitrile

Procedure

The title compound was prepared analogously to Example A(97) where 6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde was substituted in place of 2-ethyl-4-methyl-1H-imidazole-5-carbaldehyde and 1-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopentanecarbonitrile (Example A(189) (was substituted in place of 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile. 1H NMR (400 MHz, CDCl3) δ: 1.41-1.98 (m, 17H), 2.30-2.68 (m, 6H), 3.62 (d, J=16 Hz, 1H), 3.71 (d, J=16 Hz, 1H), 6.99-7.03 (m, 2H), 7.21-7.25 (m, 1H), 8.74 (s, 1H), 9.45 (s, 1H), 10.8 (s, 1H). Anal. Calcd. For C30H31ClFN5O3: C, 63.88; H, 5.54; N, 12.42. Found: C, 63.73; H, 5.71; N, 12.17. MS (ESI): 564 (M+H)+.

Sources & evidence

ORD record
ord-607716989d7d4548b1504aa038e79350
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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