L-Malic Acid → (2S)-3-(3-{5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)-2-hydroxypropanoic acid

HRID 561235Notes

Reaction equation

HRID 561235 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.[C:25]([OH:33])(=[O:32])[C@H:26]([CH2:28][C:29](O)=O)[OH:27]>>[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:29]([CH2:28][C@H:26]([OH:27])[C:25]([OH:33])=[O:32])[O:19][N:18]=3)=[N:13][N:12]=2)[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 222656L-Malic AcidHCID 1363601515-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-N'-hydroxy-1,3,4-thiadiazole-2-carboximidamide

Product 1

HCID 59738194(2S)-3-(3-{5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)-2-hydroxypropanoic acid

Procedure

The title compound was prepared in a similar manner as described for Example 16 from 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-N′-hydroxy-1,3,4-thiadiazole-2-carboximidamide and (S)-(−)-malic acid.

Sources & evidence

ORD record
ord-97355bc80a274058845262eb47c88613
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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