Hydrochloric Acid → (3S)-1-((1R)-2,2,2-trifluoro-1-(3-(3-fluoro-7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine

HRID 339098Notes

Reaction equation

HRID 339098 reaction equation
[F:1][C:2]([F:43])([F:42])[C@H:3]([N:29]1[CH2:33][CH2:32][C@H:31]([NH:34]C(=O)OC(C)(C)C)[CH2:30]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[C:22]([F:23])=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1.Cl>C(Cl)Cl.CC(O)C>[F:43][C:2]([F:1])([F:42])[C@H:3]([N:29]1[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[C:22]([F:23])=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86707560tert-butyl (3S)-1-((1R)-2,2,2-trifluoro-1-(3-(3-fluoro-7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707561(3S)-1-((1R)-2,2,2-trifluoro-1-(3-(3-fluoro-7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amineYield 85%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3S)-1-((1R)-2,2,2-trifluoro-1-(3-(3-fluoro-7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.096 g, 0.159 mmol) in DCM (0.5 mL) was added 5 N HCl (0.530 mL, 2.65 mmol) in IPA. The reaction mixture was stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure. The crude residue was suspended in ACN (5 mL) and stirred at ambient temperature for 10 minutes. The solid was collected by filtration to give (3S)-1-((1R)-2,2,2-trifluoro-1-(3-(3-fluoro-7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine (0.078 g, 0.135 mmol, 85% yield) as a solid. LCMS APCI (+) m/z 505 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringstirred at ambient temperature for 10 minutes
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-420350054cee4c7893411c310c3f2240
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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