[(4R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl fluoride → (5R)-5-[(3-{5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-one

HRID 561233Notes

Reaction equation

HRID 561233 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[S:15][C:14]([C:16](=[N:18][OH:19])[NH2:17])=[N:13][N:12]=2)[CH2:7][CH2:6]1.[CH3:25][C:26]1([CH3:36])[O:30][C@H:29]([CH2:31][C:32](F)=O)[C:28](=[O:35])[O:27]1>>[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[S:15][C:14]([C:16]3[N:17]=[C:32]([CH2:31][C@H:29]4[O:30][C:26]([CH3:36])([CH3:25])[O:27][C:28]4=[O:35])[O:19][N:18]=3)=[N:13][N:12]=2)[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 86620466[(4R)-2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl fluorideHCID 1363601515-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-N'-hydroxy-1,3,4-thiadiazole-2-carboximidamide

Product 1

HCID 66696815(5R)-5-[(3-{5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-one

Procedure

The title compound was prepared in a similar manner as described for Example 13, step 2 from 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-N′-hydroxy-1,3,4-thiadiazole-2-carboximidamide and [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl fluoride.

Sources & evidence

ORD record
ord-59db6cf7f7dd4057b5451508086d8329
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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