Hydrochloric Acid → (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-(3-methoxypropoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine dihydrochloride

HRID 339047Notes

Reaction equation

HRID 339047 reaction equation
[F:1][C:2]([F:44])([F:43])[C@H:3]([N:30]1[CH2:34][CH2:33][C@H:32]([NH:35]C(=O)OC(C)(C)C)[CH2:31]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][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=[C:18]([F:23])[CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1.[ClH:45]>ClCCl.C(#N)C>[ClH:45].[ClH:45].[F:44][C:2]([F:1])([F:43])[C@H:3]([N:30]1[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31]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][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=[C:18]([F:23])[CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86707536tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-(3-methoxypropoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707537(S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-(3-methoxypropoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine dihydrochlorideYield 169.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-(3-methoxypropoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.12 g, 0.19 mmol) in dichloromethane (1 mL) was added hydrochloric acid (5-6M in 2-propanol; 6.5 mL, 0.19 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes. The solvent was removed under reduced pressure, and the solid obtained was suspended in acetonitrile (3 mL) and stirred at ambient temperature for 5 minutes. The solid formed was collected by vacuum filtration to give the title compound (0.095 g, 80%). FIA-MS APCI (+) m/z 519 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solid obtained
  3. stirringstirred at ambient temperature for 5 minutes
  4. customThe solid formed
  5. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-186189bdf51f42edbf8526fa32854083
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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