Hydrochloric Acid → (S)-3-(8-fluoro-1-(pyrrolidin-3-ylamino)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 1476879Notes

Reaction equation

HRID 1476879 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([NH: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]([NH: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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136597077(S)-tert-butyl 3-((8-fluoro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)amino)pyrrolidine-1-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 136596991(S)-3-(8-fluoro-1-(pyrrolidin-3-ylamino)isoquinolin-3-yl)-1H-1,2,4-triazol-5(4H)-oneYield 99.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of (S)-tert-butyl 3-((8-fluoro-3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)isoquinolin-1-yl)amino)pyrrolidine-1-carboxylate (300 mg, 0.72 mmol) in EtOAc (5 mL) was added a 4M solution of HCl in EtOAc (5 mL). The reaction mixture was stirred at RT for 45 minutes. The solvent was removed in vacuo to give an HCl salt of the title compound (250 mg, 99.2%). ESI-MS m/z [M+H]+ 315.2.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-be1698dff6d7465eb6bd6f49b5cecff8
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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