1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile → 2-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-propionitrile

HRID 858695Notes

Reaction equation

HRID 858695 reaction equation
[CH:1]1([C:6]([OH:32])([CH2:22][C:23]2[O:24][C:25]([CH3:31])([CH3:30])[O:26][C:27](=[O:29])[CH:28]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:19]#[N:20])CC[CH2:16]3)=[C:11]([F:21])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.BrC1C=CC(C(C)C#N)=C(F)C=1.BrC1C=CC(C2(C#N)CCC2)=C(F)C=1>>[CH:1]1([C:6]([OH:32])([CH2:22][C:23]2[O:24][C:25]([CH3:31])([CH3:30])[O:26][C:27](=[O:29])[CH:28]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:16])[C:19]#[N:20])=[C:11]([F:21])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 587622991-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrileHCID 587623452-(4-Bromo-2-fluorophenyl)propanenitrileHCID 587626531-(4-Bromo-2-fluorophenyl)cyclobutanecarbonitrile

Product 1

HCID 587625582-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-propionitrile

Procedure

The title compound was prepared analogously to 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile in step 3 of example A(236) substituting 2-(4-bromo-2-fluoro-phenyl)-propionitrile from step 1 below in place of 1-(4-bromo-2-fluoro-phenyl)-cyclobutanecarbonitrile. MS (ESI): 437.0 (M+H+).

Sources & evidence

ORD record
ord-7622c5fe2e8f41ed92c6ec223aa4b9b3
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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