Hydrochloric Acid → 4-(4-bromophenyl)-5-[(3S)-3-pyrrolidinylmethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one Hydrochloride

HRID 525239Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][N:10]=[C:9]2[CH2:14][C@@H:15]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]2)=[CH:4][CH:3]=1.O1CCOCC1.[ClH:33]>>[ClH:33].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([CH2:14][C@@H:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)=[N:10][NH:11][C:12]2=[O:13])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 673758331,1-dimethylethyl (3S)-3-{[4-(4-bromophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-1-pyrrolidinecarboxylate

Product 1

HCID 673774324-(4-bromophenyl)-5-[(3S)-3-pyrrolidinylmethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one HydrochlorideYield 96%

Procedure

In a round bottom flask under nitrogen, 1,1-dimethylethyl (3S)-3-{[4-(4-bromophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-1-pyrrolidinecarboxylate (3.54 mmol) in 4M HCl in dioxane (40 mmol) was stirred at room temperature for 2 h. The solvent was removed by concentration in vacuo to give the title compound as the HCl salt (1.25 g, 96% yield). MS(ES)+ m/e 322.9, 325.0 [M+H]+.

Workup

customThe solvent was removed by concentration in vacuo

Sources & evidence

ORD record: ord-1b8ec3ef22de4cfda4dd71fc9839068c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340529B2

Reaction notes

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