Hydrogen chloride-ethyl acetate → (S)-3-(8-fluoro-1-(pyrrolidin-3-yloxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 1476875Notes

Reaction equation

HRID 1476875 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([O:12][C@H:13]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)=[N:9][C:8]([C:25]1[NH:29][C:28](=[O:30])[NH:27][N:26]=1)=[CH:7]2.[ClH:31].CCOC(C)=O>>[ClH:31].[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([O:12][C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)=[N:9][C:8]([C:25]1[NH:29][C:28](=[O:30])[NH:27][N:26]=1)=[CH:7]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 136596973(S)-tert-butyl 3-((8-fluoro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 136597052(S)-3-(8-fluoro-1-(pyrrolidin-3-yloxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-oneYield 100%

Procedure

A solution of (S)-tert-butyl 3-((8-fluoro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate (90 mg, 0.224 mmol) in HCl/EtOAc (4M, 10 mL) was stirred at RT for 2 hours. The mixture was subsequently concentrated in vacuo to give an HCl salt of title compound (80 mg, 100%).

Workup

  1. concentrationThe mixture was subsequently concentrated in vacuo

Sources & evidence

ORD record
ord-316677ae938841cc91c349432faab701
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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