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

HRID 858663Notes

Reaction equation

HRID 858663 reaction equation
C1(C2(CCC3C=CC(C(C)(C)C#N)=C(F)C=3)CC(O)=C(CC3NC(CC)=NC=3C)C(=O)O2)CCCC1.[CH:37]1([C:42]2([CH2:50][CH2:51][C:52]3[CH:57]=[CH:56][C:55]([C:58]4([C:63]#[N:64])[CH2:62][CH2:61][CH2:60][CH2:59]4)=[C:54]([F:65])[CH:53]=3)[CH2:47][C:46](=[O:48])[CH2:45][C:44](=[O:49])[O:43]2)[CH2:41][CH2:40][CH2:39][CH2:38]1.C1(C2(CCC3C=CC(C(C)(C)C#N)=C(F)C=3)CC(O)=CC(=O)O2)CCCC1.[CH3:93][C:94]1[CH:99]=[C:98]([CH3:100])[N:97]2[N:101]=[C:102]([CH:104]=O)[N:103]=[C:96]2[N:95]=1.C(C1NC(C=O)=C(C)N=1)C>>[CH:37]1([C:42]2([CH2:50][CH2:51][C:52]3[CH:57]=[CH:56][C:55]([C:58]4([C:63]#[N:64])[CH2:59][CH2:60][CH2:61][CH2:62]4)=[C:54]([F:65])[CH:53]=3)[CH2:47][C:46]([OH:48])=[C:45]([CH2:104][C:102]3[N:103]=[C:96]4[N:95]=[C:94]([CH3:93])[CH:99]=[C:98]([CH3:100])[N:97]4[N:101]=3)[C:44](=[O:49])[O:43]2)[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 5

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587623021-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopentanecarbonitrileHCID 688686862-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl]-2-methylpropanenitrileHCID 1784376152-[4-(2-{2-cyclopentyl-5-[(2-ethyl-4-methyl-1H-imidazol-5-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-fluorophenyl]-2-methylpropanenitrileHCID 178437630HCID 178437630, compound

Product 1

HCID 587624291-(4-{2-[2-Cyclopentyl-5-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-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) 2-[4-(2-{2-cyclopentyl-5-[(2-ethyl-4-methyl-1H-imidazol-5-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-fluorophenyl]-2-methylpropanenitrile where 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 and 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde was substituted in place of 2-ethyl-4-methyl-1H-imidazole-5-carbaldehyde. 1H NMR (400 MHz, CDCl3) δ: 1.44–1.96 (m, 17 H), 2.14–2.22 (m, 2H), 2.56–2.62 (m, 8 H), 2.70–2.74 (m, 2 H), 3.79 (d, J=16 Hz, 1 H), 3.92 (d, J=16 Hz, 1 H), 7.12 (s, 1 H), 7.24 (s, 1 H), 7.26 (d, J=5 Hz, 1 H), 7.42–7.47 (m, 1 H), 10.9 (s, 1 H). Anal. Calcd. For C32H36FN5O3: C, 68.92; H, 6.51; N, 12.56. Found: C, 68.74; H, 6.60; N, 12.47. MS (ESI): 558 (M+H)+.

Sources & evidence

ORD record
ord-e2178fddffac43c99a2fbd9663a5cedc
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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