Trifluoroacetic acid → (S)-3-(8-(pyrrolidin-3-ylamino)-1,7-naphthyridin-6-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 1476861Notes

Reaction equation

HRID 1476861 reaction equation
[O:1]=[C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([NH:17][C@H:18]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]4)[N:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:20]1[CH2:21][CH2:22][C@H:18]([NH:17][C:15]2[N:16]=[C:7]([C:4]3[NH:3][C:2](=[O:1])[NH:6][N:5]=3)[CH:8]=[C:9]3[C:14]=2[N:13]=[CH:12][CH:11]=[CH:10]3)[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136597000(S)-tert-butyl 3-((6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-1,7-naphthyridin-8-yl)amino)pyrrolidine-1-carboxylate

Product 1

HCID 136596924(S)-3-(8-(pyrrolidin-3-ylamino)-1,7-naphthyridin-6-yl)-1H-1,2,4-triazol-5(4H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-tert-butyl 3-((6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-1,7-naphthyridin-8-yl)amino)pyrrolidine-1-carboxylate (80 mg, 0.201 mmol) in DCM (3 mL) was treated with TFA (1.5 mL) for 2 hours. The solvent was removed in vacuo to give the title compound, which was used in the next step without further purification.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1cfb119ce47d4d9bafd3c9395b8aa822
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…