Trifluoroacetic acid → (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine
Reaction equation
[F:1][C:2]([F:42])([F:41])[C@H:3]([N:28]1[CH2:32][CH2:31][C@H:30]([NH:33]C(=O)OC(C)(C)C)[CH2:29]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[C:16]([O:24][CH:25]([CH3:27])[CH3:26])[CH:17]=[C:18]([F:23])[CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1.C(O)(C(F)(F)F)=O>>[F:42][C:2]([F:1])([F:41])[C@H:3]([N:28]1[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[C:16]([O:24][CH:25]([CH3:27])[CH3:26])[CH:17]=[C:18]([F:23])[CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1Participants
3
Reactant 2
Product 1
Procedure
To tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (120 mg, 0.204 mmol) was added TFA (2 mL) and the reaction was stirred for 30 minutes. After concentrating to dryness, the residue was dissolved in methanol and added to 2N HCl in ether. The resulting solid was filtered and dried under high vacuum to yield (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine (105 mg, 105% yield) hydrochloride as a beige solid. LCMS APCI (+) m/z 489 (M+H). Specific rotation: [α]26D=+1.43° (c=0.93, MeOH).