(S)-tert-butyl 3-((7-chloro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate → (S)-3-(7-chloro-1-(pyrrolidin-3-yloxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 1476884Notes

Reaction equation

HRID 1476884 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:25]3[NH:29][C:28](=[O:30])[NH:27][N:26]=3)[N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)=[CH:4][CH:3]=1>Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:25]3[NH:29][C:28](=[O:30])[NH:27][N:26]=3)[N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 136597003(S)-tert-butyl 3-((7-chloro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate

Product 1

HCID 136596960(S)-3-(7-chloro-1-(pyrrolidin-3-yloxy)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-oneYield 117.2%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A solution of (S)-tert-butyl 3-((7-chloro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate (200 mg, 0.463 mmol) in 4M HCl/EtOAc (5 mL) was stirred at RT for 2 hours. The reaction mixture was subsequently concentrated in vacuo to give the title compound (180 mg, 100%).

Workup

  1. concentrationThe reaction mixture was subsequently concentrated in vacuo

Sources & evidence

ORD record
ord-1996309a1fdd4c06b9eb97e8c556372a
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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