3-Bromo-1,2-oxazole → 1-(4,5-dihydroisoxazol-3-yl)-1H-1,2,4-triazole-3-carboxylic acid

HRID 1746135Notes

Reaction equation

HRID 1746135 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][N:3]=1.C[O:8][C:9]([C:11]1[N:15]=[CH:14][NH:13][N:12]=1)=[O:10]>>[O:4]1[CH2:5][CH2:6][C:2]([N:13]2[CH:14]=[N:15][C:11]([C:9]([OH:10])=[O:8])=[N:12]2)=[N:3]1

Participants

3

Reactant 2

HCID 139338913-Bromo-1,2-oxazoleHCID 178499122HCID 178499122, compound

Product 1

HCID 866505651-(4,5-dihydroisoxazol-3-yl)-1H-1,2,4-triazole-3-carboxylic acid

Procedure

1-(4,5-dihydroisoxazol-3-yl)-1H-1,2,4-triazole-3-carboxylic acid I-171a and I-171b were prepared using the analogous procedure to Example 35 except that racemic compound I-75 was used as the starting bromo-isoxazole and 1H-1,2,4-triazole-3-carboxylic acid methyl ester as the nucleophile Additionally, at some point during the course of the reaction or workup, the ester hydrolyzed to the corresponding acid. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M−H]−=356.6 m/z. Activity: C

Workup

  1. customduring the course of the reaction or workup
  2. customThese compounds can be separated

Sources & evidence

ORD record
ord-7adede485c544c839a26c6e1342f94cb
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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